WTF with Marc Maron Podcast - Episode 800 - Jeff Ross

Episode Date: April 6, 2017

For the 800th episode of WTF, Marc welcomes back the show's very first guest, Jeff Ross. Just as WTF evolved since that first episode in 2009, Jeff evolved from the Roastmaster General to a comedian using his talent as a put-down artist in order to help us all better understand each other. He also talks about the unique relationships he built along the way with people like Buddy Hackett, Billy Crystal, Sid Caesar, Mel Brooks and, yes, Donald Trump. This episode is sponsored by Louis CK 2017 on Netflix, 2 Dope Queens on Spotify, and Kabbage. Sign up here for WTF+ to get the full show archives and weekly bonus material! https://plus.acast.com/s/wtf-with-marc-maron-podcast. Hosted on Acast. See acast.com/privacy for more information.

Death is in our air. This year's most anticipated series, FX's Shogun, only on Disney+. We live and we die. We control nothing beyond that. An epic saga based on the global best-selling novel by James Clavel. To show your true heart is to risk your life.

When I die here, you'll never leave Japan alive. FX's Shogun, a new original series streaming February 27th, exclusively on Disney Plus. 18 plus subscription required. T's and C's apply. Hi, it's Terry O'Reilly, host of Under the Influence. Recently, we created an episode on cannabis marketing with cannabis legalization. It's a brand new challenging marketing category.

legalization. It's a brand new challenging marketing category. And I want to let you know we've produced a special bonus podcast episode where I talk to an actual cannabis producer. I wanted to know how a producer becomes licensed, how a cannabis company competes with big corporations, how a cannabis company markets its products in such a highly regulated category and what the term dignified consumption actually means. I think you'll find the answers interesting and surprising. Hear it now on Under the Influence with Terry O'Reilly. This bonus episode is brought to you by the Ontario Cannabis Store and ACAS Creative. Lock the gates! and ACAS Creative. What the fuck, buddies? What the fucksters? What the fucking ears? What the fucking elics? What the fucking avians?

What the fuck, Arikans? What the fuck, Tuckians? What the fuck, Minster Fullers? What the fuck, O'Barry Fins? And the list goes on. I can't go through it all, but I thought I'd do a little more than usual at the beginning to make this episode a bit special because it is a marker but after a certain point markers as good as they are how many you know what are you going to do wait we're all getting older right and the show today is the 800th 800th episode of wtf 800 episodes astoundingounding. We've done different things at these milestones, and as the time goes on, they just become another day, but you do want to mark it because it is sort of an astounding thing.

thing let's let's get into the what we're doing here today in a second let me let me first get out that uh you know i've got a few tour dates coming out and i always like to have you guys and gals you people you folks i i like you to come uh i'm doing i'm going to be in boulder colorado tomorrow night at the boulder theater i'll be at the paramount theater on saturday in denver colorado the aladdin theater uh in portland on april 21st and 22nd they added a late show in portland on the 22nd on the saturday i believe there's still some tickets for that left milwaukee that needs a little love come on milwaukee april 27th at the papst the orpheum in madison wisconsin let's go midwest all right april 28th the pantages theater i'll be shooting my special for netflix on april 29th on april 29th in minneapolis there's two shows

uh i believe those are selling well but that second show let's go may 12th philadelphia at the miriam theater and may 13th dc at the warner theater not many tickets left for that dc show and the philly's going good they're all going really good but that one man that one in milwaukee what is it what i do to you milwaukee? Huh? Where we at? 800 fucking episodes. That is crazy. Today on the show, my guest is Jeff Ross. And that's for a reason. And I'll tell you what it is. Jeff Ross was actually the very first guest on WTF. It was a different show then. Now, I would like to tell you that as of today, WTF has been downloaded more than 330 million times. That's a lot of times. That's a lot of downloads, man. The first episode we did was recorded at the end of August in 2009. And we posted it on September 1st, 2009.

Now, where we were at, we had hijacked the studio at the Old Air America. Me and my producer and business partner, Brendan McDonald, were out of work because they canceled the streaming video show we were doing on there so we wanted to throw something together and we had done radio together we'd done me and brendan had been working together in in some form or another since 2004 so we were like let's figure out this podcast thing now we didn't really have a plan at the beginning. Not unlike I enter most conversations, there was no plan for the show other than we wanted to feel it out, figure something out. There were three segments on the first episode. There was a story about feeling morally justified stealing stevia from Whole Foods, which also

became an essay in my book. Stealing Stevia from Whole Foods, which also became an essay in my book. We talked to Jeff Ross, who was on the phone, and we did a WTF moment at a Ralph Lauren store. Now, the original intention of the show was for it to have a variety of segments, all right, which we did for the first few dozen episodes. There was some movie talk. There was some conversations with my father it was a kind of a variety show to a degree but there was this umbrella idea of what the fuck you know the most important philosophical question is not the meaning of life it's what the fuck and it was really that was the spirit that ran through the thing now jeff ended up being our first guest i because at that not

unlike now there were certain guests and at that time we had no track record who were out doing things and you know we could get them and i knew i wanted to talk to comics i liked comics i was a comic i am a comic i know how to talk to comics we're all of the same community but we had put a few in the can these shorter conversations uh with i think patton was on the phone over his book i think john oliver and we had those in the can and we were we had some things with to work with to put together the first show and maybe i should play this thing because because this was interesting listening back to this show because obviously the show became a very different thing over time.

You know, once I got out here, we had sort of foregone the multi-segment format. No more phone interviews. I can't stand doing phone interviews. Rare occasions where a friend of mine needs to plug something. For most of the hundreds of episodes, there's really no phone interviews. Face-to-face was what I wanted to do. At the beginning, for a while, we had a third part to the show, a third segment. That was an interview with a guest that may or may not be real.

And it was more to work with improvisers and do that kind of thing and improvise. But then it sort of evolved into what it's become, which is a, a, a candid, connected, genuine conversation as best I can do with somebody. But what was interesting in listening to this first episode was that we pulled this clip. Now, I don't know that there was ever a mission statement, but, but, but this was as close as I could find to it in this first show. Listen to this. I just felt like it was time to do this. It was time to focus.

It was time to ask these questions about mundane things, about political things, about personal things, and just getting out there again. I know a lot of you have listened to me in many different forms over the years, and I think this will be the freest of all of them. This will be the most unfiltered and the most representative of where I'm at, and I'll try to keep it as personal as possible. And also, I just don't know what the fuck half the time so i hopefully you know through this show and through uh hanging out with you people and my friends and some comedians we're gonna have jeff ross on here

in just a bit so you heard that the amazing thing about that is all of that remains pretty true including the fact that we're gonna have jeff ross on in just a bit here but what sort of evolved you know in the show is we were never rigid about the format. We basically let things evolve. We always knew why we were doing it. Because of where I was at my life and because we were hungry and wanting to do something, it wasn't so much ambition. It was a compulsion. We had this need to create a connection. And the true evolution was realizing the true connection happening during intimate, empathetic conversation. And that's really like you'll hear, that's ultimately the difference between Jeff in show number one and Jeff in show 800. He never got

his full hour interview. This is his real WTF interview the interview that that the show evolved into what we do here was a great conversation and it was interesting because at the beginning you know i was calling my friends so we could have some funny conversation yeah i mean that was it you know you get some laughs you can always count on a comedian i mean i knew that from doing radio when i did radio both as a a host of a radio show and as somebody who appeared on radio when the comic walked in you're like if this guy's on his game you know my my job is going to be easier so when i'm a guest on a radio show i always try to show up be present be funny go with the flow and when i had people on my radio show you were hoping for the same thing sometimes people shit the bed but i knew comics were dependable but what i didn't understand about

me and about comedians was that it's one thing to get to turn to a comic to get some laughs and good feelings the other thing is turning that comic into a person to find out more about who he is and what i learned over time and if you'll listen to the first many episodes and talking about comics, was that we're very well-equipped, most of us comics, to have conversations about anything because that's what we do. We sit and think about things, about everything.

And we live our weird lives that are outside of the mainstream, for the most part, I would say for all of it, we're a bunch of gypsies and rogues and strange people, perverts, heavy hearted, depressives, hyperactive, compulsive, needy, funny, loving, sensitive, all the good things too. A lot of times I forget to put the,

to compliment the bad list with the good list. And it's not, it's just human comics were my entry into being a person who was empathetic in conversation who enjoyed listening to people i mean i had i hadn't really had that since i was a kid because i'd gotten cynical and and just to you know to really learn things about not only people, but about life. And the difference between number one and 800 is profound, but the evolution makes perfect sense in that we honored that original idea. But to mark this part of the evolution by talking to jeff jeff who is you know really in terms of personality and being and and comedic style is a a kind of ever-present voice in comedy since the beginning of comedy in a way and i talked to him a little bit about that but

yeah before i go into this conversation i I do want to say thank you all. And thank you to everybody who's new, to everybody who's been through it with me. Thank you for hanging out. We were able to really make something here and to continue to make something. And every time I come into this garage, no matter how much I'm full of anxiety or panic or dread or whatever's going on in my life me in that orange chair across the way and I connect and we start talking, all that other stuff, all that other stuff goes away and I'm locked in and I'm listening and I'm engaged with another human being and I'm engaged with you guys out there, you people out there. I know that you're listening in and that what's happening is something profoundly human and profoundly good

and profoundly necessary especially in the culture we live in today where these kind of connections aren't made you know as much as they should if at all on a day-to-day basis as you know if i don't talk to someone in here a couple times a week i start to get squirrely and cranky and aggravated. And I need to do that thing that we all need to do effortlessly is, Hey man, how's it going? What's up? I'm okay. Not really. Really? Where, where have you been? What happened there? How's everything, uh, you know know at home yeah that you got to do that and you got to listen sometimes all it takes to show up for somebody else in a very deep and real way is to listen Listen. It's important.

Doesn't take much to be there for other people most of the time. Thank you very much for listening. This is me and Jeff Ross. Finally, he gets his full WTF treatment 800 episodes later after being in the bathtub on the first episode

talking to me from the Bellagio Hotel. This is me and Jeff just a couple of days. It's winter and you can get anything you need delivered with Uber Eats. Well, almost, almost anything. So no, you can't get snowballs on Uber Eats. But meatballs, mozzarella balls, and arancini balls? Yes, we deliver those. Moose? No. But moose head? Yes. Because that's alcohol, and we deliver that too. Along with your favorite restaurant food, groceries, and other everyday essentials.

Order Uber Eats now. For alcohol, you must be legal drinking age. Please enjoy responsibly. Product availability varies by region. See app for details. Death is in our air. This year's most anticipated series, FX's Shogun, only on Disney+.

We live and we die. We control nothing beyond that. An epic saga based on the global best-selling novel by James Clavel. To show your true heart is to risk your life. Will I die here? You'll never leave Japan alive. FX's Shogun, a new original series,

streaming February 27th, exclusively on Disney+. 18 plus subscription required. T's and C's apply. Go. Jeff Ross. Hi, bud. It's good to see you, man. This is cool. I can't believe you've never been here. The legendary garage.

I know, but you've never been here. Congratulations, man. Thank you. 800 episodes. This is it. The idea was you were on the first episode so why not be on the last but who the hell knows when that's gonna happen so we'll put you on the 800 the real issue isn't how you managed 800 episodes yeah that's how you managed to stop

talking and long enough to upload them what is what is it a roast now what is that what we're gonna do 800 episodes, buddy. Can you believe it, man? It's really incredible. I went to your Wikipedia page, and the first thing on your credits is you did the first episode of the WTF podcast, September 1st, 2009. That's a credit. I was in a bathtub at the Borgata Casino. I remember.

I don't remember what we talked about. It was only like 20 minutes. It was before the show was like it is now. no we talked about dancing with the stars i think is that what you were doing then yeah i just done in the middle of it but but it wasn't like a like a real w you know wtf interview wasn't the hour sit down i can't believe it's been so long dude i don't know anybody maybe ace was doing a podcast before you but i don't know anybody else was really into that but the weird thing is i've known you i feel like since we were children yeah you remember that picture you tweeted out the other day it was me and you and todd and louie and moon yeah everybody with hair i remember you from even further back than that let's let's just

put it in perspective like when did i ever you? How did I feel about you? Let's go real classic Marin conversation. I can't believe I'm talking about myself in the third person. I remember you were getting spots at Catch a Rising Star before most of us, before me or Todd. You had sort of a mulledy, dewy, curly thing, but it was definitely mulledy. You always wore a jean jacket, and your name was Jeff Lifsholtz. If I recall correctly, you had buttons on that fucking jacket most jackets have buttons no i mean like pins did you have pins oh that sounds like something i could have had

you don't you don't remember come on no i mean i wore weird stuff back then i would wear bracelets and clogs and right you know i was a little weird no but this was before you were a hippie you know before that period where i think you might have called me lift schultz but i was probably at that point performing as when did you start man i remember you as jeff my first time on stage was exactly april 1st 1989 i wouldn't have met you that first year no because i was in new york i was there i was on the Lower East Side starting 89. I moved down from Boston, and I was trying to get in. So I was at the Boston Comedy Club in 89.

Then you were probably doing spots, and I was probably on open mic or trying to get on the shows you were on. Really? I just remember you getting past a catch pretty early. That is a great memory. That is something that happened. I got past there before anywhere else, which was usually people's last club for some reason.

It was my first pass. I never really got past there. And I remember bringing, like, Lewis a present. Lewis Ferranda? Yeah. From Catch a Rising Star? He gave me my first $20 in the business. He put me up at the end of the night.

Yeah. And he saw something in me that up at the end of the night. Yeah. And he saw something in me that I didn't yet see in myself. Yeah, I didn't see it. No, I mean, you know, I don't hold a grudge against people who didn't see it in the beginning. You can. I always tell comics that. Like, you get better. Of course.

No one has time for somebody who's not funny. I remember when you got funny. I remember when Todd got funny. I remember when I got funny. It was just Todd got funny. I remember when I got funny. It was just like four years ago. It happened very late. Those early days, man. You only start out once, right?

But I remember, you remember we used to go over to the Ukrainian place, the Kiev? I still do. Oh, well, not the Kiev, but Veselka's. I go to Veselka's too. But like the Kiev was sort of the place. It was like me and you and Louie and Todd and Sarah and Attell. That was like the joint. It was kind of dirty, not as good as a Veselka,

but I don't think the Veselka was open 24 hours at that time. We would commiserate. Sure, yeah. Miserable commiserate. Is that part of that word? Sure, and I would say things like, how'd you get into catch? Why'd you get past? I brought a vest for Louis.

I bought him a present. Did you? And then when my grandfather died, he gave me like a little pep talk. He's like, now it's time for you. You got to think about you for a little while. Because I was taking care of my grandfather in New Jersey. And yeah, and I thought about those days recently because they were like cutting funding for Meals on Wheels.

And I remember taking the bus into New York every day from New Jersey. And then Meals on Wheels would check in on my grandpa. Yeah. They'd bring him a hot meal. Yeah. And make sure he's alive for the next 12 hours while I was trying to find work in New York. Trying to get on stage. Trying to start my life.

How old were you? 23, 4. So you grew up in Jersey? Yeah. What part? Newark, Union, and Springfield. Oh, yeah? And you got like a sister, right?

I kind of have bits and pieces. My sister Robin, she's a special ed teacher up in Washington State. So what were you doing in there? What kind of family situation? What did your old man do my dad my grandfather my uncles everyone in my family was a caterer my everyone my great grandmother rose who i'm technically named after ross is uh was a was a very rare female business owner back in the like 40s and 50s.

Clinton Manor Caterers. Clinton Manor. I worked there every summer. I worked there every weekend, all through junior high and high school and even parts of college. She owned that? Yeah. And they'd do events?

They would do weddings and bar mitzvahs and trade shows and that kind of thing. Kosher. Oh, it was kosher. And back when people were having big kosher weddings really and then i worked in you know in the coat room as a kid and then and then and then made meatballs and wound up feeding the help and working in the parking lot and once i got to college i was like i don't think i'm gonna be a caterer i think i'm gonna try something else you're gonna break the tradition yeah so was your dad the last one? My dad and my cousin.

Of the Rolf Schultz caterers? Well, my dad passed away. It basically became my cousin's, and his heart wasn't in it really. And it kind of fell off. I remember you telling me about your dad passing away. Because I remember the one time we had this conversation. I can't remember. It must have been down in front of the Boston.

I think I was all worked up because I didn't understand. You were driving some fancy car, like a Dodge Viper maybe. What a memory. Is that true? Yeah. But all right. So when did your dad pass away? My dad when I was in high school, in college.

What happened? Yeah, he did cocaine. Oh, yeah? Living the life? He had a good time. Yeah. Had a cerebral hemorrhage. Was in a coma for a few days.

Came home from BU, and that was it. That was it? And your mom had been gone for a while, right? Yeah. She'd already been gone five years. Wow, man. So you were kind of just you and your sis, huh? Yep.

Still is. Well, we have a you were kind of just you and your sis, huh? Yep. Still is. We have a good family and we're okay. We all get together quite often. I just got a beach house at the Jersey Shore for a couple weeks this summer. 25 of us will pile into that. The cousins and everything? Aunt and uncle and cousins. You're all so tight.

That's great. We do it for real. Do you feel connected to Jersey? I feel connected to the people. I don't know if i feel connected to the state right but you feel you're jersey yeah yeah like when you were when you were in high school you were you a bruce guy of course yeah of course but i feel like i would have been a bruce guy no matter where i was from or wherever he was from i think he he... It was in the stars. I learned a lot about performing, I think, watching those early Bruce shows.

You know how he goes fast and then he goes slow. Then he gets two fast ones and he goes slow. Well, what did you learn exactly? Just showmanship. Just to stay slow? Just to mix it up and keep the audience surprised. And the intimacy, even in a big theater like that. Sure.

And just that you could stay true to yourself. And we all aspire to have that kind of impact on their audience. I think that's a good observation. I think him in particular is unique to that himself. It feels earnest. It feels real. You feel special to be there. And he really turns it out.

It took me a long time to appreciate it. I think I appreciate it more now because I talk to him yeah you know it was a great interview and he also taught you talked about how you know you can open up on stage where maybe you can't open up off stage so easy and that was a good breakthrough and i think that's why a lot of us get drawn to the stage it's weird right yeah our Our lives offstage are just a mess. And then onstage, maybe you're not. You always seem kind of chipper. I'm doing okay.

I have my moments. Yeah? What are they like? Are they crying moments or yelling moments? I think the worst I ever got was probably a year ago. I came home from a road gig, and I just wasn't happy for some reason. And I grabbed a baseball bat and just started slamming the bed. Oh, really?

Just beating my bed. You didn't want to risk breaking anything. Yeah. Well, that's good. Did it feel good? It felt cathartic. Yeah? But I think for pretty much I'm pretty even-tempered.

Yeah, I feel that from you. So you grew up in Jersey. You're doing the catering. Now, were there – there did you see stand up at the catering hall where did you see your first stand up like who who were your guys earlier i had no idea i didn't know what any of that was you didn't know the jew comics no i heard their voices on johnny carson because my parents would watch it and i'd be upstairs trying to listen huh Huh. But I didn't know from the old time comics. Because like I was so into them when I was a kid. And you're only a couple of years younger than me.

Like I would look, I would watch, you know, Buddy Hackett and Rickles, all the guys that you got to know later, which I envy. But they were the guys I watched when I was a kid and I loved them. Jackie Vernon. Yeah, I didn't know until later. And everyone said, well, you must have been influenced by them it wasn't it wasn't like that for me i was influenced by the rock star comics eddie murphy yeah blues brother steve martin cheech and chong that's what i didn't even know that that was

comedy i just thought that was the same as i bought their albums at the same way i bought kiss or boston or oh yeah yeah stuff like that so i didn't even i didn't know about the the tuxedo comics until i was meeting them but you weren't also you didn't know about the culture of stand-up you didn't really acknowledge that there were this world of stand-ups no i had no idea it was alien to me i thought to be a comic i would have to be like the guys i'd seen pictures of or on johnny carson like you know, Hackett, Rickles, those guys. But I didn't feel a connection to them until later. But you didn't know their work even.

Right. And I also, it's weird. Like, people wonder about that because of the Rosen. Did you know those guys? It was more like I felt like I'd met guys I should have known my whole life. Well, I mean, I feel that too about you. You know, because I remember when we were coming up in the late 80s and early 90s,

you know, everybody had their own unique thing and you weren't really doing insult comedy at all. No. You were doing observational stuff, kind of long form-ish. Yeah. Yeah. Stories and poems and... Well, the poems came later, though. Yeah. That was later, dude. Yeah. Wasn't it? I mean, it was just straight up

observational comedy. Right. at a very deliberately slow pace. You know, I didn't know what I was doing. I was a film major in college and a political science minor trying to go. Yeah. Were we there together? No. You're a little bit ahead of me, maybe. But, you know, I was still running the radio station.

I was a music director and a DJ. At BU? in a punk band you did yeah i became a political science minor and i went to russia with my class and with political science yeah what'd you do in russia uh i wound up looking around it was during the refuseniks youiks. I remember meeting with Refuseniks and sneaking their art back to America, thinking I was doing something really cool and special. What'd you bring back? Just these guys. There was a real problem for artists, and Jews were scared, I remember. And I just remember going to a couple of houses and poking around and meeting people.

I was a kid yeah but i was also curious and also fearless my dad had just died i had nothing to do that's that christmas yeah my sister was with her friends yeah for christmas so i was like all right fuck it i'm gonna go to russia the soviet union yeah in the winter yeah and find out about vodka and eggnog and and everything else that we were trying to that was it everything else vodka and eggnog and the big list after that i just remembered doing those two drinks for the first time in my life i remember it was just super super exciting to be in a foreign foreign foreign country completely unleashed didn't have to worry

about calling home or disappointing anyone or my life became very unhinged in a series of happy accidents after after Russia after death yeah you go alright like him I guess I can do whatever I want this is kind of no parents you know when to tell me this isn't a good idea disagree you know but I also didn't have the support to write it what your grandparents didn't step in or anything? They were all gone. I had the one grandfather who I really took care of. So that is kind of bizarre.

Like you're sort of orphaned at 19 or whatever. Yeah. And you're still not completely grown up. Right. Wow. I don't know if I ever grew up. Yeah, I'm not sure I did either. Look at us.

I know we're doing okay for children. It is crazy. I do think sometimes sometimes like i never feel old and i never feel young i always felt this way since i'm 15 you know what i think has something to do with that with us we have no children must be part of it i think you know you have children you're like i'm yeah it's happening if they're getting taller i'm getting older right but we're just suspended in some strange non-growth thing, you know, emotionally or otherwise. But, all right, so when did comedy start?

So you go to Russia, you come back a changed man, you're drunk. You know, it's just more like experiences. The following year, I think I went off to Scotland with another college buddy and just seeing the world. And I knew I wanted to do something different. I just didn't know what it was. I kept thinking, I'm going to have a weird life. I just don't know what it is. Yeah. And I remember, I'm going to have a weird life. I just don't know what it is. Yeah.

And I remember like coming out of college, I started a production company with my college buddy, Brian, and we were epitome productions, making training films and trying to do commercials for like health and beauty aid stores. In Jersey? In New York City. So it was this weird little, like. I would take the bus every day.

I live in a house i grew up in my grandfather was now living with me came out of the bronx to live with me because we were both kind of on our own he was widowed and i was orphaned was he together yeah oh cool this is the greatest i'm wearing his ring right now oh that's cool it's a bolt from a nazi submarine that he took apart when he was in the u.s coast guard oh really yeah steel bolt i wear all the time i took off him right when he died was he one of the caterers or the other when he was in the U.S. Coast Guard. Oh, really? Yeah. Steel bolt that I wear all the time. I took off him right when he died. Was he one of the caterers or the other side? No, he was from the other side of the family.

He was a construction worker. Oh, okay. Tough guy. Very funny, very awesome, my best friend. Yeah, you don't hear about tough Jews enough. Do you know what I mean? He was the toughest. He was a foreman in Bronx Construction Union.

So he had to really like pretend. He was tough and he had to even pretend he was tougher than he was to get respect. Yeah, that's what always annoys me about the characterization of, you know, elites or the, you know, Jews run this or that. Is that there was that whole generation that he comes from that came over here, you know, from Europe or the generation after that. that he comes from, that came over here from Europe or the generation after that. There was a bunch of Jewish boxers, construction foremen, plumbers, cops. It was a whole...

There were some tough fucking guys. Yeah, you had to be. Yeah, to get by. Right. He'd get in fights with the Irish guys or something, or he'd have to exert his authority to different groups that were construction workers. And I just remember him telling me these stories and stuff.

And he's always kind of, he's always had like big hands and big arms and he was tough. Yeah. Tough juice. Yeah. James Caan style. My grandfather would give me money for the tolls. Yeah.

And a banana. Take a banana for the ride and I would go into the city and hit the open mics. So that started after the production company? What happened? We were failing quickly. We tried everything. We tried a home investment video,

home video with Louis Rukeyser from Wall Street League, and when he figured out we were 25, he was like, I'm just going to steal this idea from them and do it myself, and he did. And that was very successful for him. And then you knew how. That was your first lesson in show business. Yeah.

I realized how show business could really fuck me up when he finally died and I was happy. Like 20 years later, my friend. But you carried it with you. Brian called me up and said, guess who died? I'm like, Louis Rukeyser. You know. And I just kept searching.

And another buddy, my pal Mark Chapin, said, I'm taking this writing class in New York City. Comedy stand-up. I think you'd be good at it. Who taught that? Lee Frank. Lee Frank. Hi, Lee. What happened to Lee Frank?

Lee's around. I just talked to him. He's writing on a show right now. He's doing great. He's out here? Yeah. Oh, that's amazing. That's around. I just talked to him. He's writing on a show right now. He's doing great. Out here? Yeah. Oh, that's amazing. That's great.

I remember Lee Frank. Great teacher. Taught me a lot of cool stuff about stand-up and encouraged me to keep going. Because there were the two. There was Blakeman and Frank, I guess, who taught the classes. I guess so. Lee Frank. Yeah, great teacher.

Yeah, I remember him. I remember him as a stand-up. He told me if it doesn't offend somebody somewhere, it's probably not funny. That's pretty good. I was like, that's words to live by for a comic. I loved it right away. I was like, wow, I get to say whatever I want. This is always what I loved about America.

Freedom of speech. Yeah. I was always that kid drawing swastikas on my notebooks, just doing anything you could to... I did that too. I was like, oh, it's a free country. I can do whatever I... I can say whatever I want.

You just hit this weird memory with me when I was in like second grade. I think I was at Hebrew school and I drew Hitler. Pushing buttons is what it is. Yeah, I don't know what I was doing or thinking, but I got turned on by the idea of freedom of speech. So when somebody said,

you can just go on stage and just talk for five minutes about whatever you want, I thought, well, if I ever do this once on television, I wouldn't care if I ever did it again. Just the idea that you can have that platform. And then, of course, once I started doing it, I was like, wow, all right, this is a good way to meet girls. This is a good way to make money.

This is a good way to express myself. It gave me a social life and immediately you know quickly over time to it i took right to it even though there was a lot of haters telling me i was crazy like i still had my production company it was in a in the marbridge building and in on 34th and broadway it was all shoe uh retail uh shoe wholesalers in that building. I remember like the guy next door saying, so you guys are closing up your production company. Yeah, he goes, what are you going to do? I go, well, I've been trying stand-up.

He goes, oh, well, you'll figure something out. Tapped me on the shoulder and wished me luck. And, you know, the family was like rolling their eyes. But you started doing the open mics. Who did you meet first? Oh, wow. I remember Johnny Lampert telling me, don't go to catch. They'll never pass you.

He would give me like, if you get heckled, say this. And he would give me Dangerfield lines. Yeah. So I think he was sabotaging me. Oh, really? So that if I said those, Lewis would go, that's stolen. Oh, really? Yeah, I do think he was.

He set me up. I never asked him, but he would be like, that's why. Now I know why. He'd say, if somebody messes with you, say, now I know why lions eat their young. Like, it was like those kind of, I think he was testing me to see if I had ever heard any of this. I hadn't. Yeah.

But you didn't do it. I didn't. I kind of caught that. It's didn't sound right coming out of me. Who else was hanging around? So that was Todd Barry and I were the two backups at catch. Yeah. Cause Todd used to go up there and sit there and I would not go up there.

Right. That was where I would get on early on. And then I broke in downtown, stand up New York, theork the boston comedy who was on the stage of ketching like i'm trying to remember oh well that was amazing what what era that was oh well that was like early mario joiner and john stewart was the was the big um closing act he wasn't famous but he was a killer yeah right yeah i remember he would just lay flat on the stage and yell up the ceiling and he had that dirty denim jacket on and boots and he was fearless and he was cool and he was jewish and i was like that guy's cool what's his name oh it used to be leibovitz oh maybe i can pull off jeff ross instead of changing let me use my middle name like he did and i was like okay that was it

that's what inspired you it wasn't even a jew thing. It was more like when I finally got on TV on Star Search a couple years later, they had to use a smaller font to fit Lipschultz. And I was so humiliated about Ed McMahon mispronouncing Lipschultz three times. Every time I won, it was like, you're a challenger, Jeff Lipschitz. And I was like, oh. And I wasn't strong enough of a comic to like not let that stuff bother me now it's stuff i don't care but sure well you gotta get you got tough before i did i'll tell you that i mean maran moron it never ends m-a-r-k marin mark with a k moron yeah try lip shits every

time well you you solved that problem right you changed it like you know like all of them do like all of those jews it wasn't a never a jewish thing it was always a show business if you're gonna be in show business i was flying home from star search and i said either i'm gonna have to change my stage name or my entire family is gonna have to change their last name that was your first tv thing the The Star Search? Probably, yeah. And that was, okay, so you're kicking around with Stewart. This is what, in 90, 89, 90? Right. Mattel was kind of hosting them.

I remember Reggie McFadden, Sarah Silverman bopping around the third street, borrowing money from me so she could give it to homeless people. It does occur to me like the jobs, the the gigs the tv shows can come and go but it's these relationships that sustain us you know look how long we know each other yeah you know why they sustain us is because we're all selfish and we're and and generally you know the bond remains intact somehow you know like like i'm i'm you're i'm sure you have close friends but i don't hang out with too many people but every time i see you i, I don't think like, oh, what am I going to say to Jeff? You know what I mean?

You have this community where there's a shorthand to it. Right. Like when I see Todd Berry, we used to wander around all day long together and hang out. And sometimes I'm sad that we don't hang out more. But when we do hang out, you know, I'm like, well, that's enough. No, Todd has definitely evolved into a huge pain in the ass. So it's much easier to see him once in a while, give him a hug that he doesn't want, and move on.

He just did the roast battle, and he killed, but he was so hard. He's so funny, though. But he's always been. I love him, and I love Attell, but it's just in Louis. I see everybody infrequently, but it's always good to see him, and I never feel like there's a lot of distance. Well, comics, if I haven't seen you in a while i don't have to say hi how are you what have you been up to i could just say how's the crowd i like your boots and you know

that i'm saying how are you yeah and i i would see you at different times but all right so you do star search did you win i won one and lost one what the big prize no i won the first round and i stayed an extra few days it was very exciting because i'd never been on a show that were other people that weren't comedians on it yeah singers and dancers and yeah keith robinson was down there and he helped me keep drag i really went to win i brought like two duffel bags of clothes yeah and thought i was going to be there for two months i was there for four days the. The core group, it seemed, that I was friends with, and you were always part of it, although you were up to catch a little more,

it was me, you, Etel, Louie, Sarah, Todd. Well, you remember the ones who rise to the top. But we were hanging out. I mean, I remember hanging out with you guys, right? Of course. Well, the alt-comedy scene. We were doing rebar. I mean, we were all that's rebar i mean you were we were all

doing our open mics downtown but in addition to that a scene came out of it yeah but that was the weird thing and that's what i really think gelled a lot of it but where you would actually remember it because instead of just being friends we were now like doing interviews together and people would come cover these things that's right there's we would do festivals together i remember being an aspen for the first time when you were there. Oh, for Comedy Central. Yeah, I remember us all auditioning

for Letterman together. That's right. And you not getting it. We're at Stand Up New York. Yeah. But let's talk about that because we weren't doing, like the way alternative comedy happened

in New York City was different than in Los Angeles because in Los Angeles, you know, it was like Dana Gould and Kathy Griffin and the Uncabaret and then the bookstore and this and that. But we, all the guys in New York that started it, were working at clubs.

It wasn't like we were some nerd crew that wasn't working. No, their whole thing out here was much different. Our thing in New York was a new space. Literally alternative, like a break from what we were doing at 2 a.m right trying to get on in the real clubs right and suddenly like someone said hey tell a story right what we're going to do without a stage maybe not even a microphone

do you remember though the very first one before rebar there was like two at that place you had to walk upstairs no no that was after rebar But the very first one you hosted it, the actual eating it show by that was put together by Michael O'Brien, Dave Becky. That there was one show that we all did before Rebar and then Rebar, which was a very impractical performing situation. But that's where it became a thing. Was it Rebar? I remember I remember learning so much about myself from that scene because, you know, I wasn't an actor. I wasn't a real entertainer. I was just basically putting a, you know, trying stand-up. Yeah.

Not really popping, not getting on the late night shows or MTV or any of those shows. Right. I was not quite there yet. But alternative comedy kind of loosened me up where I wasn't afraid to try to tell just a story. Me too. And not worry about the laughs per minute. Me too. I just started talking about my grandfather.

And I remember I got encouraged to talk more and more about my life. And it kind of freed me up as, you know, I was always loved Garrison Keillor and that kind of stuff. I was like, okay, maybe I don't have to be so sticky. Maybe I could just talk. And that led to me going, what else can I do that I don't realize I could do? And that's when I started doing the roast. I was like, I went to the roast as alternative comedy.

I was like, it was like a hoot. Yeah. I was like, oh, this is weird. Well, wait, let's fill in some gaps. So you're working at Catch, and we're doing Boston, and then we got this alternative thing. And I think, like, the rebar thing, I think that's where that picture of us was taken with Moon,

was at the rebar. Okay. And then it moves to Luna thing. And I think like the rebar thing, I think that's where that picture of us was taken with Moon was at the rebar. Okay. And then it moves to Luna, which is a different situation, but it's already hot and it becomes like, I didn't even realize how hot it was. I was sweaty and on Coke and yelling. But right. But you, I remember because you and Alon Gold were Friars and there was this weird push. When did you join the Friars Club?

96 maybe. Oh, that late? That's about right. I was the last one of that group. Because I remember Elan. I couldn't afford it. Was like, you know, come on, let's make it young and hip. Like, they have a gym there.

It's like, really? And I remember I went up there and I'm like, I can't. I can't do this. I mean, I love these old men, but, you know, but I can't. What am I going to do up here? I'm going to sit and watch Alan King eat? I love that. So, yeah.

To me, that would go, yeah. So, when did you go the first row? So, it was before you joined the Friars Club? No. That's how I joined. I got invited there to play poker a few times. With? Judy Gold, Elon Gold, and Greg Fitzsimmons is what I remember.

Okay, I remember. Right. Greg's dad had been an influential member. Right, he was part of it. The next wave of Friars. Bob Fitzsimmons is what I remember. Okay, I remember, right. Greg's dad had been an influential member. Right, he was part of it, right. The next wave of Friars. Bob Fitzsimmons. Yeah. And I remember I got him to play poker.

It was like, I would always play poker in, you know- Mark Cohen's house? Mark Cohen's overheated studio. Yeah. So now to suddenly be at the Friars Club where a waiter comes up and says, would you like chicken salad or tuna salad? You know, and you're getting a drink while you're playing in a special air-conditioned room.

Right. Instead of, you know. Instead of in bong smoke. Right. With four other comics. Seven other comics. So suddenly it felt very, I don't know, showbiz. Legit.

Right. Yeah. And I loved it. I just loved that. old school though greg fitzsimmons asked me to perform at the bob fitzsimmons memorial golf tournament for his dad honoring his dad and the charity out in jersey yeah and i didn't play golf so i showed up just in time for the show and they were all drunk all the friars guys freddie roman was hosting yeah and he liked shit on me when he introduced me i never met him yeah and i was like oh well here's an easy target and i just for the sake of survival yeah started goofing on him they call him freddie roman

because he talks so loud you can hear him in italy or something like that just light-hearted did it work it killed i didn't think much of it it just kind of of did a favor for Greg. And then like a month later, Jean-Pierre Trebeau, the head of the Friars, called me up and said, would you like to roast Steven Seagal? And I was like, why? They're like, well, that's how we do our roasts. And there was no YouTube. I couldn't Google it back then. So I went to the Museum of Broadcasting and I looked up the roasts. The Dean Martin. And I saw, oh, it's not just Steven Seagal who I didn't Google it back then, so I went to the Museum of Broadcasting, and I looked up the roast, Dean Martin, and I saw, oh, it's not just Steven Seagal, who I didn't care about.

It was Henny Youngman and Milton Berle and Buddy Hackett would all be there. I was like, all right, I think I could get that. And that, to me, sounded like another ambitious attempt at alternative comedy. Like, oh, let me try writing this kind of comedy. So, like, old-timey. So there was an ironic thing to it? No, not old timey, but pointed. Okay.

About a certain person on a certain date. But it's a class. What they call special material. Right. You know? Yeah. And I thought, oh, okay, that could be fun. Like putting a suit on and riffing with these legends at one in the afternoon, that was

really different it was yeah yeah yeah and of course you todd and a couple other people made fun of me when i would go back down to rebar or luna lounge to the alt scene yeah and i go this is the ultimate in an alternative what are you talking about you guys are being pussies they're like you're going to some safe old jewish thing that we're trying to forget about. And the Friars and all that wasn't cool then. It's right after Whoopi Goldberg and Ted Danson caused a stir with blackface. But it was also in-house. This is before they were televising the roast. It hadn't been televised since Dean Martin and that was its own thing. But the Friars roast was an in-house thing. Was it an honor to be roasted? Is that why they did it? Yeah, they would do a career achievement

or a man of the year kind of thing. So who was that first one, Steven Seagal? Steven Seagal was being roasted. Milton Berle hosted it. It was his last time emceeing one in 1990. And you'd never met him before? No, I didn't meet him until he introduced me on the dais. Yeah, who else was there?

Buddy. Yeah, had you met him? No, I didn't meet any of these, never met any of these guys. This was the first time you met Buddy Hackett, Milton Ber Yeah, who else was there? Buddy. Yeah, had you met him? No, I didn't meet any of these, never met any of these guys. This was the first time you met Buddy Hackett, Milton Berle, who else? Right, and I walked right into it. There's always those other weird people

like Patricia Hurst would be there and the mayor, David Dinkins, would be there and Leon Spinks and Michael Spinks and Don King, you know? So it was like, oh, well, not only am I not performing for like drunks at 1 a.m., these are like New York socialites and people who I didn't have to dumb it down for. Like I could try to write the smartest jokes I could think of. Right.

And I really took to that. So Milton brings you up. Oh, terrible intro. Just back from Vegas where he performed at a convention for lesbians with dildo rash. And he lost a look at the card again to remember my name. And of course, you know, I'm on late. Yeah. Some guys killed, some guys bombed.

Yeah. And did you do well? Yeah, I did very well. My first time, I had some good jokes, but I had way too many. So my opening joke was, I looked at Steven Seagal, I shook his hand. There's 2,000 people to New York Hilton. I realize a lot of you don't know me, but I feel uniquely qualified to be here today because I'm also a shitty actor.

Oh, so it was one of those ones i'm like got my one suit on that i bought to do letterman maybe one day or went for a wedding yeah you know so and and i have my notes and every time i got a big laugh milton would poke me right in the ribs from behind the dais only i could no one could see it and after three or four times i'm like what the fuck are you doing milton like it was driving me crazy yeah everyone thought i had like a tick and he's like he's like just starts messing with me so i had a few you know sort of riffing with him yeah and that must have been great and it was good and he kind of wouldn't let it go and finally from like 20 yards down the dais buddy hackett was like milton let kid work. Remember when you used to work? And that was it.

Milton ran down the dais, kissed Buddy on the lips. I made some joke about the two of them fucking after the show. And that was it. I have pictures in my house. You were in. Of Milton like hugging me and Buddy taking me out after. And Milton, I said to him, I asked Buddy, why would Milton have done that?

And Buddy said, Milton doesn't like when a new guy gets big laughs. And I asked Milton, you know, after that, we'd go back to the Friars Club after. Buddy would be drinking in one room and Milton would be smoking in another room. And they'd both hold court in separate rooms. Yeah. Because one didn't like drinking and one didn't like smoking. Yeah. And Milton said, you know, well, you had good jokes, but

they only remember the home runs. Just tell the home runs. And I was like, oh, that's a good lesson. So he didn't like that I was going on too long. That's what he claimed. So it was a good lesson. I remember that all the time. It's like, you don't need to tell every joke you think of. You need to narrow it down and destroy. Yeah.'s a that's a good note for me to take right now i'm trying to put together an hour when did you make sort of like feel like this was your thing like you know outside of enjoying doing it at one in the afternoon or at the hilton when did you realize it yeah i i did it for fun for fun and i was like wow i'm really good at this yeah i got everyone i need everyone to see it somehow yeah that's when i talked to friars and comedy central and drew carrie into getting letting it be on tv yeah and what was the first one drew it was drew carrie is to comedy what mariah carrie

is to comedy that's a good one that was your opening yeah so so you do drew and they put it on comedy central and they put it on Comedy Central. I remember right at the beginning, those deuses were fucking huge. Yeah. Why? They had like 30 people. Why? Because the Friars would always invite every cool person that might want to come that was a celebrity.

And then Freddie Roman would go on before the actual roast started and have everyone famous take a bow. And there'd be like every actress who's ever been on a soap opera, whoever was on Broadway at that point. We would have people like the police commissioner would come. The Friars was very, it was a scene. Yeah, it was.

And it was something they only did once a year at noon for two and a half hours. So everybody had to see it. Howard Stern would sit in the balcony out of firing range just because he loved watching it. only did once a year at noon for two and a half hours so everybody had to see it so howard stern would sit in the balcony out of rain out of firing range just because he loved watching it so you always wanted to kill because everybody was there from donald trump to howard stern to the mayor to the police commissioner to to all these notorious boxers and and and it's where it's where mobsters would mix with politicians and it was okay.

Right. And I love that. Out in front of people. Like Seagal invited all these mobsters, but yet there was also like, you know. It's New York. Yeah. That was New York. It was very pure and I love that

and I love being part of something that was different than the normal late night comedy scene. Sure. My parents loved those guys. Don, Buddy and Don and those kind of guys so i was like there's a lot of like god i wish they were here kind of moments while i was sitting there yeah but my friends came and my family my cousins and they'd always come my aunt and uncle got real supportive and they loved meeting everybody so i got a big kick out of it too

so who did which one of the old guys did you become real friends with? Yeah, right? Buddy and I were like brothers. He's a Jersey guy. He was originally from Hackensack. Yeah. His name was actually Buddy Hacker. Really? His real name, Leonard Hacker.

I loved him when I was a kid. I sent away for an autographed picture to him when I was probably 14. And he sent it. I got one. I got to be better. I get emails. Can I enter on there. And he sent it. I got one. I got to be better. I get emails. Can I enter on there? And I just delete. I usually send the pictures.

I don't get a lot of them because it's sort of a dated thing. But I'll send them usually. I got to get better at outreach. I don't send just the autographs. Because then what happens is, like, who are those guys that hang outside at Kimmel and Conan that want you to sign shit? I'm like, what do you think you're going to get for that? You know the guys I'm talking about? There's like four of them. Yeah. And they have these signed pictures. Somehow they already have eight pictures of you to sign shit. I'm like, what do you think you're going to get for that? You know the guys I'm talking about?

There's like four of them. Yeah. And they have these signed pictures. Somehow they already have eight pictures of you in a folder. Exactly. You don't even know how they know you were going to be there. Right. How did you know I was on a Southwest connecting flight?

With eight pictures of me dressed like Gaddafi. Yeah. What are they doing with those? All right. So you do Drew Carey and that's a success for Comedy Central? Yeah, so much so that we did a bunch more with the Friars and then we did Hugh Hefner going into 9-11. That was a big one.

Going into 9-11? Well, 9-11 happened and we had a roast scheduled for like two or three weeks later. Did you do it? We wound up doing it and canceling the after party and using that money towards the Twin Towers Fund. Yeah. And it was a big thing.

I was a producer on the show. That was a horrible time, man, for months after that. It still smelled in New York. Oh, terrible. But we had to decide whether to go ahead with the show. And I wrote a letter, which I still have somewhere, to the Friars to hef and to comedy central saying this is before it was a cliched expression i said if we cancel the terrorists

win this one let's not have a party yeah let's put the money towards the charities and go on with the show and and and and start to shake this off a little bit yeah and did it work it worked it was a great one of the best roasts ever that's the one where gilbert did the aristocrats oh yeah jimmy kimmel hosted yeah and it was like adam carolla sarah silverman cedric the entertainer plus like tons of other cool people that went on to become a huge star steve carell stephen colbert triumph Triumph, Patty Hearst, Rich Eisen. They were all there just as guests. Like we kind of got whoever we could get after 9-11 just to be there.

Yeah. And you were the producer. You were brought in as the producer. That was your thing? I wasn't brought in. I was like, you know, I would help people write their material. I got a co-producer credit or something. I was making very little money.

And was Barry Katz involved in that? I was doing it strictly for the love of the game at that point. That was always what was fascinating. I don't think what people know about the roast is that from the very beginning, you guys, you put together a team of writers to help people out? At that point, we had no team and no money. It was just like who wanted to try to get this going and who wanted to help out and who wanted a credit?

Who wanted to get their jokes on. Yeah. Yeah. Because that way you could say, hey, I wrote some jokes for Kevin James. Whatever. You know, when he roasted Jerry Stiller. Kevin's funny. Yeah.

He was good. That was always the goal, to just get some jokes on. They were like currency. You had the jokes, you know, tell me your best joke. Everywhere I went, people wanted to hear the roast jokes. Yeah. And also, because they're roast jokes, if you get, like, eventually you got writers to, because they'd be like, there's these guys would show up, like, here's a bunch of, you take what you want.

Right. You're like, all right. And I got better at recognizing if somebody was funny, like, oh, I'd heard that, or that seems derivative. Or people would go, well, can't you just mix them up and rewrite them for the guy you're roasting? And I'd go, some people can, but I'm now under the pressure of being good at this. Yeah. And I kept thinking for those first five or ten roasts, like, all right, well, now I've done three in a row where I killed, five in a row where I've killed, eight in a row.

This is going to turn bad eventually. Right. But it never did. I just kept doing it. You got better at it. Yeah. I mean, it is a specific form. And I remember when I did it,

I'm not good at insulting people if I'm not mad at them. So I think I could probably do it better now. Right. But some guys were just great at it. They just found that tone. You, Geraldo, was very good at it. I miss that guy.

I mean, right now, could you imagine what he would be doing? The work he would be doing? Yeah. The resistance? It's crazy he's not around. Yeah. So you did roast Trump. I roasted Trump 2005 and then again 2000

before. I've roasted him twice. Was it on TV? One was, one wasn't. And what was your impression of him? I mean, you saw him a lot. He was always around. Oh, I traveled with him. He hired me.

For what? I went to Mar-a-Lago. Yeah? Performed in his clubs. Yeah? Plane. Really? You've been on the plane?

Been on the plane. Now, let's say he's not president. He was fun. He was? Yeah. Yeah? He was really fun. Charming.

Paid well. Yeah. Great sense of humor. Good host. He was waking up, would blow off, talk in business to talk comedy. Are you surprised by the turn of events? Yeah. Yeah.

It's intense. Yeah. It's intense. Yeah. To know that guy. I ran into him over Christmas in Florida. Had a nice chat. Really?

Still loves comedy. After he was president? No. After he won and before he became president. Yeah. And he was still sort of like, how you doing, buddy?

Dipping his cheeseburger in mayonnaise. Having a good time. I asked him, how you doing, buddy? Dipping his cheeseburger in mayonnaise. Having a good time. I asked him, I said, what would Joan have thought about all this? Joan? Because he loved Joan Rivers. Oh. And she won that Apprentice show.

Yeah. And he's like, she wrote me a letter years ago encouraging me to run for president. And I was like, I don't know, man. She would have given you a hard time about a lot of this stuff. He kind of shrugged it off like maybe, but he didn't think so. Is your impression of him that it's really about him most of the time? Do you know what I mean? I know you don't really talk politics, but do you think he really wanted to be president?

I think he wanted to win. I don't know if he wants to be president. Yeah. I think he wanted to be, for a minute, because he's skipping the fun parts of being president, like the victory lap, the White House Correspondents Dinner, where he got roasted. You thought for sure he'd want to go up and go,

ah, you got me once, but now look who's here, and throwing out the first pitch and all that stuff. He's missing that. So I think this could be bad for his health. Well, yeah. I think it's going to be bad for everybody's health. It's starting to look like. That's understood.

You asked me about the man. Yeah. Right. No, I agree with that. I look at him. He's eating too much. He doesn't look well very quickly. Right. No, I agree with that. I look at him, he's eating too much. He doesn't look well very quickly. Right.

But the weird thing is that people who live in New York, people like you, who were sort of ingrained in the fabric of the city for all those years, knew him. He was a guy. He was a New York phenomenon and was very part of the fabric of that city in a very sort of prominent and entertaining way for one way or the other. He was brash. Yeah. And he represented like you know no bullshit New York. Right. I want to build an ice skating rink right here. Wollman rink. If he put that kind of effort that he put into the Wollman rink into health care he would have passed it. Sure. He had a real tenacity that represented New York well. When he had control. Yeah, he's an old school Queens style. Well, it does frustrate me when people underestimate him

and go, well, he's tweeting all night. He's not carefully thinking about this stuff. I go, this guy builds skyscrapers. He's diabolical. He's patient. Don't underestimate him. Yeah, and that's a warning this is not we're not i i i do think that it is yeah underestimating him is is a

hobby in this country well yeah but i think uh right but i think there's a mixture of uh like uh wanting to think it's chaotic and also being terrified. I don't know that anyone's necessarily underestimating him. They just don't know what the fuck he's going to do next. And now he's working with all these factions that he never had to work with. And now he's what he represents politically because of how he chose to do it and who he chose to surround himself with. He's not, you know, that, you know, whatever charm that he had when he wasn't this powerful

is diminished for a lot of people. But, all right, so what was the Bea Arthur thing? She showed up at Jerry Stiller's roast. Yeah. Jerry Stiller was an interesting guy to roast because he fully understood the honor of it. Like to him, it was his Oscar. Right. He couldn't believe that he had had a career that now was going to be honored.

In a roast. In that way. Yeah. In New York. Yeah. career that now was going to be honored in a row in that way yeah in new york yeah and it was one of the first times where his son and him were going to be on stage together yeah ben was now the biggest movie star in the country doing like you know cool movies with janine garofalo was there it was like super hip yeah so now the roast was getting suddenly like a little hip factor to it and it was going to be on tv and um jerry invited all his old school funny friends yeah and b arthur came and i see b arthur is on the dais but not speaking now i am in awe of that woman i mean yeah maude the golden girl yeah she was the funniest

to me yeah and i remember thinking wow it's so weird that she'd just be sitting there but never be acknowledged uh-huh never take a bow never speak it was like that to me that was strange yeah so i was like i gotta find a way to mention her. And I had my jokes that I worked. Didn't realize she was going to be there, so I didn't write about her or anything. It was about Jerry. But I just sort of wrote in my margin on my script, be Arthur's dick. Yeah.

Didn't know what the joke would be or what would happen, but I thought if I'm killing and there's a space to think, maybe there's something there about her dick. I don't know why. Maybe someone said something. I don't know if I'd heard that in the walk out to the kitchen if someone said, I don't know where it came from. I honestly don't. Yeah, yeah.

And we're doing the roast, we're doing the roast, and dirty words like Jerry would kind of squirm. He's still kind of like that. Yeah. Old school. Sandra Bernhard went on right before me. Yeah. Which she sang a sexy, seductive, lap-dancy version

of Magic Man, I think, to Jerry. She like grinded on him to embarrass him. Yeah. And I was next. Sandra Bernhardt, holy shit, I wouldn't fuck you with Bea Arthur's dick. The joke's okay. It's pretty great.

But what made it a home run was, they only remember the home runs, what made it a home run was Bea leering at me, giving me a huge take. Like her head just turning around yeah on the jumbo tron you know yeah in the big screen and just making that triple into a grand slam yeah so then now they holding on they're holding on her well she's just looking no one's mentioned her for an hour and a half i'm like at the end like she's just been sitting there yeah so you know anybody's fair game at a roast yeah and i just kept hearing about that joke yeah somebody wrote about it in time out mag new york and then you know i'd go on morning radio shows to promote my gigs and suddenly i'm like i'm

hearing about this every single where i place i go i go, she must be hearing about it. And she was doing a one-woman show in L.A., and I was like, you know what, I'm going to go thank her and make sure she's okay with it and say hi so that when I get asked about it, I can say she took it well. I didn't know anything about her. I didn't see her after. I didn't know her. And I tracked her down, and I went to her show.

She did this beautiful show where she sang and told stories. She was barefoot and I waited the whole line of well-wishers. I got in at the very end. I had flowers. I wore a suit, a seersucker suit. It was summertime. And I said, Miss Arthur, that your show was amazing tonight. I don't know if you remember me.

My name's Jeff. We met at Jerry's Roast. And before I could even get it out, she goes, you nailed me, you name's Jeff. We met at Jerry's Roast. And before I could even get it out, she goes, you nailed me, you prick. Perfect. And she took me backstage to the dressing room. Fuck this shit out of me. It's one of the greatest days of my life.

There you go. Long live Bea Arthur and her dick. So she was good with it. She was good with it. And I wound up seeing her again. She came back and did another roast for Pam Anderson. She was there, and I did another take on the same joke. How'd that go?

It was fun. It was fun. People say she got mad and left early. I don't see it that way. I think it was just long, and she didn't want to be there while Courtney Love was flashing her tits and stuff, so she split. But yeah, I mean, Bea was, you know, one of the best.

Yeah, great. So like, so you do all these roasts. You're also like, you did some writing for the Academy Awards. You were one of those guys they hired for that kind of writing, right? I remember after I did that Drew Carey roast, I sent the unedited tape to Billy Crystal. I wrote him a fan letter. Yeah. I somehow looked up where his office was.

I still lived in New York, but I sent it to LA to Maple Drive. Yeah. And I said, dude, somebody had just done the Oscars poorly. And I was like, you need to do this again. I'm a big fan. I saw him on Inside the Actor's Studio. Some of the things you said really had an impact on me. Basically, I wrote him a fan letter.

Yeah. With a VHS cassette of me roasting Drew Carey. Yeah. So if you ever host the Oscars again? It wasn't even a real job. It was like, if you ever do this again, I want to come help. Yeah. And I think a year later, Barry Katz calls me and goes,

I was on the phone with him. He's like, holy shit, David Steinberg's on the other line. And the Oscars were like about to happen again. Yeah. They had just announced Billy. Yeah. And he and he goes hold on I'll call you back that's very yeah yeah no news the only wants to meet with you in LA in two weeks yeah so now I'm like wow it worked and I get there and I'm thinking he's gonna interview me maybe I'll work on the Oscars and I walked into his office

and he shook my hand and asked me to write on the oscars before he even started to talk so it was cool i learned a lot learned you know what i learned on that one besides that i could write jokes for a big audience and and and make billy crystal laugh i learned that as hard as i was working as a struggling starting trying to make it name in new york and la he was working harder than me he was like directing a baseball movie about mantle and maris while he was hosting preparing the oscars yeah and he would write all his you know he did all the press he had the musical opening he had bits in between i was like oh okay so when you become a star you don't cruise yeah it first gets hard yeah and that was really an

eye-opening thing for me like oh okay well you know what this is good news because i have the the the the the will to work that hard where a lot of people would see that and go oh forget it right no no that was that is important lesson to learn that you it it is work it's very very hard yeah and i i learned from his work ethic. So thank you, Billy. So in all this time, so you're living your life. And how often do you hang out with Buddy? Is it a regular thing?

By then, Buddy and I became like brothers. It was almost like I was the older one and he was the... How much laughing did you do? Lots of laughing. Oh, my God. And when I had a big roast, I'd call him up and read my jokes to him and give me a few ideas. And I'd sit in his backyard when I was in L.A. and he had swings back there and he'd make matzo brie or chicken salad and we would eat. Or, you know, we'd have a drink and go to this fried chicken place in Burbank he liked.

And he would take me to poker games and And we would do animal charity gigs together. Who was he hanging around with? He was friends with a lot of animal people. Oh, yeah. It was always weird. He was friends with Dom DeLuise and his wife. And he was friends with Shecky. And he was friends with Sid Caesar.

Oh, yeah. And we would go to Norby Walter's poker game. They'd have Chinese food. Yeah. I don't think I've ever told this before, but I just remembered it the other day. Norby's an old comic? Norby was a music business guy that got kicked out of the music business for payola. Uh-huh.

But since he broke like Grandmaster Flash and all these guys. Yeah. He was legendary. Right. He got mentioned in like early 90s, late 80s rap songs. Oh, okay. So he's that guy with like gold records

all over his apartment. So you'd see him with like Grandmaster Flash and then you'd see him with like Buzz Aldrin. He was one of those guys. Yeah, yeah. So he was super cool.

But I remember he had this regular poker game. He couldn't be in the music business anymore but he still had all these Hollywood friends. So he had this nice apartment and you know like young comics would go later on but in the beginning it was just kind

of me and buddy brings me and sid caesar's playing and charles derning's playing and and charles derning had this great thing he would do once once a game yeah remember charles derning yeah of course right great great actor and he was a war hero, among other things. And when the game was particularly kind of dull, he'd wait until it gets to his bet, and he would just say, two-time Academy Award nominee Charles Durning checks. And then I remember one time, like,

Norby would put out a little Chinese buffet. Yeah. And Buddy Haggart and I are standing at the buffet. Yeah. Like, with our plates, shoveling food into our mouth, not taking the time to even sit down. Yeah. Just before the game starts, just standing there eating.

Yeah. And behind me, I look over and I see Harry Hamlin from L.A. Law, number one show at the time, tan, gorgeous, eating some fruit salad, sitting politely by himself. And I was like, buddy, that's why he looks like he looks when we look like we look. Yeah. Two fat Jewish comics eating Chinese food.

Yeah. And Bunny kind of looks at me and looks at him and he goes, yeah, but in 20 years, he'll look like shit and we'll still be funny. Another good one. Yeah, that's a good one. It's true. I saw Harry Hamlin recently. Don't look that good.

Not anymore. So you became close to Sid. You used to go to the hospital, right? I used to see Sid at his house. I would go to Sid's house. When he was sick? Yep. When he was sick.

We had my friends, my friend Fran would have these dinners in his honor for his birthday or it was a Jewish holiday. Yeah. She'd invite Carl Reiner and Mel Brooks and Dick Van Dyke and then a couple comedians that Sid liked, Richard Lewis and myself. I was always the youngest. I really had a great affection for Sid. Sid had the best laugh.

Like if you made Sid laugh, you'd think you were going to kill him. Yeah. I have a picture on my fridge in New York of Sid just laughing at a joke, at something. And, you know, it was the only time where I really saw Mel Brooks and Carl Reiner back then. And you could really see the love they had for Sid because he kind of discovered them. Sure. And I remember later, in the later times, when Sid was really kind of out of it in a wheelchair almost. And he wasn't really sure if he was there for his birthday or if he had a show.

Like he would come in and out of sort of reality. Yeah. I remember like Mel would walk in right ahead of Carl. And Mel would get on one knee right in front of the wheelchair and go, Sid. Just loud enough for me. He goes, Sid! It's your friends, Mel Brooks and Carl Ryder! And they would do it like a big opening,

like with their arms out, like a real stance. And Sid would just light up. He just loved that. That's a beautiful thing. It was amazing. It was amazing. Good friends. And I got to become friendly with those guys because of that, where they... Oh, that is so funny. It's so sweet. It's amazing. Good friends. And I got to become friendly with those guys because of that.

That is so funny. It's so sweet. It's your good friends. Yeah. But he was saying that kind of in jest, like, of course, we're your good friends. No, but because he was in and out, he just wanted to deliver it. Right. Right to him, right to his face.

And Sid would just light up. Oh, that's great. And Sid always held your hand when he talked to you. He's always real sweet. Yeah. And he never had a mean thing to say about anybody. And, you know, he would invite me to these weird things where he'd get honored by some strange, weird group. Yeah.

You know? Yeah. And I'd always come up and make a few jokes about how old he was. Uh-huh. The jokes got funnier and funnier every year. Sid got older and older. Look at this place. I've seen younger faces on cash. Right.

Yeah, yeah. Go for it. And you became friends with Mel, too? Mel was so intimidating in the beginning because it's Mel Brooks. Yeah. But we got to know each other through those Sid. He really loves Sid.

And he always thanked me for being nice to Sid. Yeah. And talking about Sid in a nice way to other people. And my Uncle Murray was in his late 80s, almost 90. He'd never been to L.A. My Uncle Murray was a caterer. Before that, he was a silver star purple heart world war ii hero medic yeah a really amazing guy yeah it also traveled the world and had the most

full life ever we called him mean murray because he was like the family ball buster he really toughened my skin up as a kid yeah so murray's never been to LA. This is like three years ago. Really? Yeah. And I said to Uncle Murray, I said, well, you're going to come to visit me. Come visit me. We'll go to Jared's Bar Mitzvah in Seattle, and then you'll come visit me for four or five days. And I go, it's a couple months out now.

I said, what do you want to do in LA you never been to Hollywood you've been all over the world three times yeah you walked across Europe in World War II you went back to every nice hotel you had the best he outlived two wives who died of breast cancer he goes I want to take a picture I want to shake hands with Mel Brooks I go well that ain't happening what else you got so I start writing Mel Brooks through his office. I knew who his assistant's name was. Yeah. And I don't hear back.

Yeah. And now my Uncle Murray's there. He's in LA. We're having fun. And it's getting closer. And he forgot about Mel Brooks and all that. And I'm taking him here and taking him there. Yeah.

And now it's Fourth of July weekend and I go, all right, fuck it. Yeah. I'm calling Mel Brooks' office. Yeah. I get the assistant. I said, I know, I kind of know Mel from Sid and this is this. And he says, you know, I think you guys, you know, my uncle's a war hero and he just wants to shake hands.

Is Mel anywhere in town? And he goes, oh, i'll tell mel you called hmm all right i have to go to the dentist my god a tooth falling out take my uncle murray to the dentist in beverly hills and it's just a miserable fucking morning yeah now i'm have nothing to do so we're just driving around beverly hills after and showing my uncle around Beverly Hills. How old is he? He's almost 90. Yeah. And at the top of Mulholland, my cell phone rings.

It's Mel. Where are you? I'm at the top of Mulholland with my Uncle Murray. I really think you guys would like each other. You have a lot in common. The only thing we have in common is that I'm a nice guy. I go, well, my you just you know come meet you just take a picture five minutes anything and all he goes i'm either going to be at my office or the barber i'll call you back in an hour and i'm panicking because i'm at the top of mulholland where my phone wouldn't work

and now it's mel brooks calling me 10 minutes later mel says can you be at my office at culver city in half an hour i go yes there at my office in Culver City in half an hour? I go, yes. There's no way we can get there in half an hour. We're in shorts. Yeah. You know, I never saw my uncle move this fast. We screech into my driveway, put on long pants,

get right back in the car. I've never seen the guy nervous. Now he's practicing lines. It's good to meet the king. Can I call you? You know, stuff like that. My uncle's really, I mean, he's done lines. It's good to meet the king. Can I call you? You know, like stuff like that. My uncle's really, I mean, he's done it all. Yeah.

But this was like making him nervous. We pull into Mel's office. My uncle had bad, bad knees. He flies right up the stairs to Mel's second floor office. Yeah. You know. Yeah. The door opens and you could tell Mel's got five minutes

yeah an hour later they're best friends they know all the same caterers the same deli owner from Brooklyn to New Jersey they both were in Patton's army they're talking Yiddish that that you know they're they're setting each other up they're my uncle was very funny they're talking Yiddish that you know they're setting each other up my uncle was very funny they're cracking each other up I can barely get a word in I don't need to get a word in I'm just watching it and they really had

it was great it was like one of the greatest things ever Mel signed a bunch of a book and gave it to my uncle and walked this out and my uncle who always had a witty comment or something to say he he walks the door closed the bell walks him out the door shuts so the office we're walking down the hallway and my uncle goes wow wow wow wow wow just can't stop saying wow we went out to eat after it was just just the greatest thing ever. And I remember him coming back to New Jersey,

telling everybody about his meeting. Never mentioned me in the story once. Just told everybody about how he hung out with Mel Brooks. And maybe six or eight months later, within a year, my uncle passed away. And I'm back talking at Sid's house. I think it might have even been Sid's funeral. I see Mel.

How's your Uncle Murray? I said, well, you know, he passed away, but what you did for him was pretty amazing. And Mel would, that whole year when I would see Mel, he would tell everybody how nice he was to my Uncle Murray. Oh, he said, how's Murray? He remembered everything about it. Yeah.

And I said, you know, Mel, it meant so much to me and if any of your uncle's ever want to have lunch with me I'm in and Mel always loves that so yeah it's great it was a cool there's a mitzvah that's really really something so what when did buddy pass away 2003 yeah that's summer suddenly attack oh that's the best way to go huh i guess he didn't take care of himself he wasn't really performing anyway he kind of had stage fright and into his 70s is that what happens a lot it does it happens people older their confidence shakes and uh well you forget how much it takes. If you're in it, you're just doing it.

And then if you get away from it, all of a sudden it's like, oh, my God, how am I going to do? Yeah. It's got to come back, right? It wasn't really performing. And I felt really lost. I had a lot of time invested in that friendship. Yeah. Like a real mentor thing. So when losing him was tough, and I really felt lost. And that's sort of when I started to find other things in my comedy.

Like what, poems? No, I went to Iraq. Oh, yeah. Not for any other reason than I didn't know what else to do with myself. But that changed your life too, right? Yeah. Performing for the troops. You mean you were existentially depressed? It's like making fun of drunk people yeah talking about like pot

and and so he has a stage and so like what you were like what am i doing with my life yeah i was single yeah and just kind of doing it for the i don't know just didn't have a purpose didn't really have a direction and a purpose and it wasn't big enough i don't know. Just didn't have a purpose. Didn't really have a direction and a purpose. It wasn't big enough. Uh-huh. I don't know. You wanted to give something back. I didn't even know that.

Yeah. But I remember I was at the improv, and Drew Carey was like, even before that one, Bob Hope died. Yeah. Now we're like at war. America's back at war, and that was depressing.

Yeah. Bob Hope dies. And I'm looking at the cover of the New York Times. And I'm sitting in Washington Square Park. And I see Bob Hope on the cover of the New York. And I never gave a shit about Bob Hope. He was so boring. Right.

Jokes were so boring to me. Like, wasn't my generation. Sure. Wasn't even my parents' generation. It was the one before Buddy Hackett. Yeah. But I noticed he lived to 100. he had all these like medals and was the only British citizen ever made an honorary vet.

Only Americans. He was British, but he only ever made an honorary vet by the military. I was like, wow, that's what a comic can do? What is that? What was that about? And then I remember showing it to my mailman in new york and there's an african-american guy in his 50s at the time yeah and like bob hope died and look and it showed and he started to get he started to get like emotional he's like i was in

vietnam and that guy showed up and he didn't have to and i was miserable i was suicidal and he made me laugh and i was like wow and then by coincidence he made me laugh. And I was like, wow. And then by coincidence, a couple of weeks later, I'm at the improv in Melrose and Kathy Kinney and Drew Carrier are like, we're going on a USO tour. And I was like, oh, that sounds wild and like a cool adventure.

Kind of reminds me when someone asked me to go to Russia after my father died. I was like, all right, I'll just go. I got nothing to do. I'll go do that. You're in the shadow of death again. And I was like, all right, I'll just go. I got nothing to do. I'll go do that. You're in the shadow of death again. And I was like, had a couple beers, and I agreed instantly,

and I woke up sober the next day and read about the UN headquarters getting bombed and Saddam's on the run, and the whole war is looking pretty ugly, and I tried to get out of it for a month. I was like, oh, God, my parents, if they were alive, they would kill me before they would let me go to a war zone. Right.

It was really intense. Yeah. And the insurgency was just starting, and I didn't want to go anymore. And I had an expired driver's license, and I had no passport, but they somehow worked it all out, even though I was trying everything I could not to go.

And my buddy Steve Ross somehow managed all the paperwork. He's a friend of mine and Drew's. And he got seven comics into Iraq around the Sunni triangle. And we did shows, a couple shows a day, Black Hawk helicopters. Our hotel was mortared, the Al Rashid Hotel in the Green Zone. Yeah. And I was like, wow, this is what it really feels like to be alive. And not only that, I'm doing comedy with a little bit of a different energy out here. And they're way more diverse and sophisticated, the audience, than I imagined they would be

watching war movies. I didn't know soldiers. Yeah. I only knew a couple of old World War II guys, my uncles. But I didn't really know what it was like to be in the military and to see that they're not like yahoos like you saw in Apocalypse Now and stuff. It was more like, oh, they're like engineers and technicians and moms and dads and every ethnicity. And it was much different than I had anticipated. And I really liked it. And I liked that everybody was thankful and gracious. And they weren't drunk. They were there. Appreciative.

Yeah, I bet. They kept thanking me for coming. And I was like, I should be thanking you. I got a lot out of this. And also, you're in the service. Yeah. I made a documentary that brought me right back to my filmmaking roots.

I shot the whole thing on that trip kind of as a home movie and then wound up realizing that some of the comics were going through something very emotional. Blake Clark was a Vietnam vet. Yeah, Blake Clark. Suddenly he's back in helicopters over a war zone and he would get very telling me these stories. very emotional. Blake Clark was a Vietnam vet. Yeah, Blake Clark. Suddenly he's back in helicopters over a war zone,

and he would get very telling me these stories. And the soldiers were telling me stuff that they wouldn't tell anyone else. They were opening up to me. So that became the next year and a half of editing this documentary of home footage called Patriot Act, and showed it at film festivals. And I think my comedy started to evolve a little bit from that. I bet you probably evolved as a person.

I think I did. Yeah. I started paying my taxes. I started voting. I got a valid driver's license. I started, like, upping my game a little bit. As a grown-up and a responsible American. And I was also doing comedy that was, you know, not quite as silly.

And roasting had a little different purpose for me there. And I was proud of the movie I made. Patriot Act, the Jeff Ross home movie. You can pick that up. I know that you shot the last special at a prison. Yeah. Now, what was the incentive for that? Well, roasting became predictable in that it was always a celebrity.

And to mix it up, I would do something different every time. Yeah. And I kept thinking, well, why do I always have to wait for celebrities? What if I just started bringing the audience up? So I started doing that in my live shows, which I still do. Yeah, And I kept thinking, well, why do I always have to wait for celebrities? What if I just started bringing the audience up? So I started doing that in my live shows, which I still do. Yeah, I've seen that. And I thought, well, what if I started roasting inanimate objects or ideas or then. Right.

I thought like crime. America was getting violent. Game of Thrones was getting big. Yeah. And video games. And I started reading a little bit about minimum drug sentencing and weird other things I didn't normally know that much about. Yeah.

And I started thinking about my own past, selling pot in high school and how lucky I was. I kind of didn't get busted or what. And I thought, like, well, what's a fun thing to roast? Like, crime in America seems interesting. Then you got to personify it somehow, and that to me meant orange jumpsuits. Now I go, how do I find a jail

that's going to let me do a show there? And would it even work? Other comics have tried. Some have done it. Paul Rodriguez. Paul Rodriguez did it. Monique did it. But they were all 20 years ago or 15 years ago,

and none of them were roasting. I spent months and months and months and months writing an act just for them yeah but didn't have a them no jail would let me in it was way too sensitive yeah and there's all kinds of laws about certain types of jokes in jail yeah like it falls under some american law where yeah you can't even do certain ethnic jokes, rape jokes, those kind of things. It's against the law to do that in a jail. So I had to find a jail that would let me in, and I finally found the one. Only one said yes, and that was in Brazos County, Texas, where they have a lot of autonomy.

The local sheriff, the jail administrator, Wayne Dickey, saw it. The local sheriff, the jail administrator, Wayne Dickey, saw it. He thought he could use it by getting his inmates to behave for a month in order to get access to the show. So admission was a month of good behavior. And they'd never had that many inmates in one room at one time, so it was a huge security issue. But they take law enforcement very seriously in Texas, almost as as seriously as i take roasting and it was a good fit and i went in i did the women's jail i did the guys and just the other day i was at a college and some kid like came running over he's like dude i was in the audience at the jail now i just saw you at florida international university I'm a freshman. It's like, it had an impact.

Yeah. And the whole theme of it is second chances. And shortly after that, the president went and spoke at a jail. And shortly after that, the Pope went to a jail in Philadelphia when he was in America. And I thought, I hadn't seen any of that before. I think I, I'm not saying I did all that but what i think i do think it helped sort of take some of the stigma out of the inmates and it made it a little cooler to talk about whereas not everybody really understood what was happening in jails just you know since then the

obama um he let a lot of non-violent drug offenders out and i think roasting can be healing and roasting can be about second chances and i found that i was doing that with celebrities like charlie sheen was having a rough year we roasted him he came back with a new show and we roasted bieber and after all his weird stuff and and acting like a punk and suddenly he had a number one album and worldwide tour and i was like what if i did did that for actual human beings who could benefit from it? It has a humanizing component. And then I went and did the cops.

The cops were getting demonized, not humanized. And I remember thinking I loved cops as a kid. They were my karate teachers. And what do cops think about what's going on with black lives matter and and and all these bad cops um upstaging the good cops so i went the only big city police department that would let me in was boston where an unarmed person hasn't been shot by the bpd since in 25 years or something so they had a lot to brag about. Yeah.

So, and community policing and stuff like that. And I thought, well, actually, cops were a very skeptical, tough crowd, much tougher than the inmates. Yeah. So that one's out there too. You can watch them both on iTunes. Jeff Ross roast cops.

Did you get them? I did. The first time I tried to perform for them, I bombed terribly. And that's in the special, actually. I mean, they protested me by not laughing. They didn't trust me. The union reps had seen that I had gone to a Black Lives Matter rally in Washington Square Park. and the brass never explained to the unions that I was coming and that I was there to be diplomatic.

Yeah. Try to find common ground. Right. But the running theme in the show is which side are you on? The Black Lives side says that, but their signs literally say which side are you on. Then the cops say you're either with us or against us. Right. And I thought, can side are you on? Then the cops say, you're either with us or against us.

Right. And I thought, can't you be on both sides? I mean, this is a complicated issue. And I don't know if it'll ever get better, but it seems like people are talking to each other more than they used to. But the second show went well? Yeah. I went back after doing a bunch of ride-alongs and winning them over, and I did a show as a copsops for Kids with Cancer fundraiser.

Yeah. So they were able to come and kind of have fun with it and loosen up a little bit, and it wound up being a pretty cool show, actually. Well, so now that we're even more polarized, and it becomes about liberals and right liberals and right wing and you know uh democrats and republicans and like i think about that a lot have you thought about how to bridge that gap yeah i do think that there's some missed opportunities lately the the one thing is i thought that white house correspondence dinner would have been a good place to find some

I thought that White House Correspondents Dinner would have been a good place to find some... Yeah, he pulled a plug on that. Yeah. To find some, you know, to find some civility between the press and the White House. Mm-hmm. And I think things, I don't know. That one's a tough one.

And how's the roast battle business? It's great. Do you think it's good for comedy? Oh, yeah. It's so good. What's your problem with it? I just never want to update. You know, it's like I love watching roasts, and I like celebrity roasts,

and I like what you do, and I like the idea of roasting. But the whole competition, I don't like competitions, comedy competitions. This is a tournament. It's not a traditional. It's not like Star Search or Last Comic Standing. Yeah. This is the only,

Roast Battle on Comedy Central, which we'll do again, is the only show where comics who aren't in the competition come to watch their friends. And it's giving voice. It's giving, a lot of the comedians who do it

are doormen at the comedy store. Right, it's very, it's specific. It's very specific. It's not like, you know, what's your best five? It's like, you know, it's got a context and, you know, you're going to go at it with this guy. Right. And there's no holds barred. And the job is to deliver the goods.

It's not like, you know, you're not sitting there going, what's my best five or how do I get on camera or whatever. No. It's like you're a soldier here. Right. Yeah. And it's, you know, you're funny or you're not funny. You kill or you don't kill. And it's giving opportunities to a lot of comedians who wouldn't get it.

They get to show off their writing. It's a lot like wrestling. Yeah. You know, people are into it. And it's one of the few safe havens left for politically incorrect or provocative comedy. We say everything. And, you know, maybe we're a little older. The young comics, they don't get offended the way older people get offended.

Yeah. So you really go. So we really go. And also it's directed at the person in front of you. Right. So as long as they're going to take it and they're all right with it, who are you to fucking judge? And it's everybody from Frank Castillo, who works the door at the comic store,

to Jimmy Carr, who's a worldwide star. You know, it's very fun to see different personalities. All levels. All levels. It's an even playing field with the roast battle. It's a great sort of equalizer in that thing. So we love doing it. And it's one of the fun. It's just also like a party.

There's always like wild scene there, and chicks, and Snoop Dogg came, and Waka Flocka was there the other day, and we just do it for fun on Tuesdays at the Comedy Store. Well, you know how to have a good time, it seems. That's the life, man. I know. And enjoy the process. That's what I always tell myself. And you've had an amazing life. I mean, even since we talked on the first WTF, I mean, all this stuff has happened.

You represent the history of comedy somehow to me. Like your grounded force that seems to have always been there and your respect and love and admiration and your ability to learn from these old guys and then honor them you know in in your life and also you know as a comic you know always touches me but now it's other stuff that you know you you know with the the troops and the prisoners and cops and you know the the equanimity if that's the right word with the young people the young comics with the roast battle you're a good guy good-hearted guy that's the right word with the young people, the young comics with the roast battle. You're a good guy, good-hearted guy.

That's nice to hear. Thank you, Mark. It's great talking to you, buddy. Let's tell a Mark Maron story real quick. You got one? So you know this story. You might not remember it, but you'll remember it in a second.

Is it going to hurt me? Nah. All right. What could hurt you at this point? Nothing. Maybe something. Go ahead. We're in Boston.

We're both Boston University college graduates now we're out of school you know I'm out a few years and Mark's probably out five years

and we're booked at some Chinese restaurant in Boston for a couple days for the Jewish thing no no no no we're like

Nick's or something one of the companies oh the Calhoun so whatever that place was. And Saugus. So Mark's headlining and I'm either emceeing or middling and we're at the condo that the club owns

in downtown Boston. Yeah. You know, it was a shitty condo but still nicer than my apartment. Thrilled to be working with a respected comedian that I kind of knew from New York but we were becoming friends that week. And we did our first night, and it went pretty well.

And maybe you weren't thrilled with your set. Maybe you were. It doesn't matter. You always had insecurities. Yeah. And you're funny, but you weren't confident. Right. And I knew you just enough to know that.

And the next morning, we're in the condo, and now there's a big headliner bedroom where you're in. Yeah. There's a little tiny MC bedroom where I'm in, and in between is a big, long living room, this roach-infested, shitty condo. And all of a sudden, about 10 10 11 in the morning you know we'd been up late i hear your door like creak open your bedroom door and i hear like like you walk across

this long linoleum floor you knock on my you crack the door open you peek one eye in I go what then your nose comes in and the rest of your face yeah I go what you go hey Jeff I go what you go I'm funny right I go yeah mark you're really funny you're really funny you're funny last night you go you go I'm. I'm going back to bed. You close the door. You went back to bed. That should be the name of your next special. I'm funny, right?

So happy anniversary. 800 episodes. Thank you, buddy. That's fucking crazy, dude. Thanks, man. Whoever thought America's alternative comic would be the biggest star fucker in Hollywood? It's a joke. It's all right. I'm funny, right? You interview celebrities. I'm funny, right? Right? Whoever thought America's alternative comic would be the biggest star fucker in Hollywood? Oof. It's a joke.

It's all right. I'm funny, right? You interview celebrities. I'm funny, right? Right? Yeah, no, it's all right. I can take a joke, Jeff, and I'm just happy that you found your groove in this very predictable format that seems to work for you over and over again. It's about roasts?

Yeah. I've made it unpredictable, didn't I? You don't know what I'm roasting next. You don't know who I'm roasting next. I don't even know how to take a shot at you. You just absorbed it, and then you made it like real conversation. It's like kung fu.

It's like verbal jujitsu. Oh, God damn it. I got to get better at it. Maybe I should do a roast battle. Why don't you come judge me one time? Okay. Warm up a little bit. All right.

See what you got. All right. Thanks for doing doing this i really appreciate it happy anniversary thank you i love jeff ross that was a nice conversation we caught up we talked about old times he shared some stories about some people it made me choke up moved me. What a great way to celebrate the 800th episode. Also, Jeff Ross is performing August 3rd at South Shore

Music Circus in Cohasset, Massachusetts. It's our old stomping grounds. August 4th at Cape Cod Melody Tent in Hyannis, Massachusetts. Go see Jeff. Thank you again. Thanks for listening. I like talking to people, and I'm glad you like listening to it and I'll play us out. I'll play us out.BELLS CHIMING Thank you. Boomer Lives!

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