Inside Late Night with Mark Malkoff - Greg Fitzsimmons

Episode Date: March 4, 2025

Greg Fitzsimmons joins Mark to discuss his Letterman debut, 40 plus Chelsea Handler appearances, Howard Stern, writing for Ellen DeGeneres, and his standup special. Official Website: https://gregfitzsimmons.com/ Stand Up Special “You Know Me”: https://www.youtube.com/watch?v=yvUqkWh_x4U Follow on X (Twitter): https://x.com/GregFitzShow Follow on IG: https://www.instagram.com/gregfitzsimmons/

Hi, I am Mark Malkoff and welcome to Inside Late Night, presented by latenighter.com. Today's guest is comedian Greg Fitzsimmons. We discuss his Letterman debut, 40 plus Chelsea Handler appearances, and much more. Now, it's time to go inside late night. Greg Fitzsimmons, nice to see you. Mark, it's a pleasure. Thanks for hanging in with me to schedule this. I know I had a lot of, I've been very busy and, and I enjoyed, I did your podcast once before, didn't I, a while ago.

I must have had a guest host of Leno or somebody else like Carson because I wasn't there, but we do have a connection. That's what I was going to mention a little bit later, but let's do it now. So I'm the door guy at the Boston Comedy Club in the mid-90s, and I have to ask you a question. Yes, it was after Neil and after Sarah, and I have to, that's Neil Brennan's, I have to ask you a question. So you would come with the book bag. You're always with the book bag just to see you're dating. You've talked about this publicly. It's in the New York Times, Sue Costello, you're dating Sue, who was going on every night at the Boston. So you would come over, but you would never go on stage when I was there. Why was that? You would just come to see Sue

and say hi, but you were doing all the other clubs and stuff. Do you remember? I mean, I used to go on the Boston a lot. I think maybe I got to where, um, I don't know. Uh, I have a theory. What? They sent me over one time to talk to Ray Romano and ask him if he would come over and do Boston. He's just like, in Louis C.K said the same thing because I had to beg him to do it and he didn't want it. Even though he helped build the Boston Comedy Club with Eddie Grill and Barry Katz, Ray's basically like, you know, my, it's like more family, more mainstream act. that Boston can be rough. I mean, I saw the Boston Comedy Club be rough. And the people, a lot of the audience wanted, some of them wanted really blue material and stuff. And the comics that didn't work that way, some of them didn't really want to be working those rooms anymore.

That's what Louis said. And he wasn't famous at the time. This was like 95 or whatever. No, I think I worked there when I first got to New York, you know, I guess, I guess it was just a lot of crowd work comics. And they would beat the shit out of the crowd. And I, didn't like the crowds it was tough that was a really tough room there would be fights i mean it was it was definitely an experience i think my focus was more on the comedy seller at that point and then i would i had a car so i used i had a mazda 626 it was beat up uh it had dense all over it i never why i was in new york city for 10 years i never watched that car one single time because i didn't want it to get stolen i wanted to look like a piece of but it had a great

engine. So I would go to stand up New York on the Upper West Side, then I would go to the comic strip on the Upper East Side, then I would swing by Carolines in Times Square, and then I would go to New York Comedy Club, and then I'd always end up at the cellar. I think Boston Comedy was a place that never really opened its arms to me, and then when I was in and I could work, I just felt like I didn't have the history there that I had in other clubs. You know, Barry Katz was there and Jason. Jason Steinberg, Jason Steinberg, our friend Jason. Jason was always good to me, but I don't know.

It just didn't feel like. I remember one time there was an audition for the MTV Half Hour Comedy Hour. There used to be a lot of auditions over there. And I remember I was just kind of coming up. I finally got in at the club. And then Jason goes, hey, there's an audition on a week from Wednesday. for the MTV for a comedy hour

and I mean my heart jumped out of my chest I was like oh my God a TV credit and so I said yeah that would be amazing and he goes all right come by Wednesday night

blah blah so I was I was doing a lot of college shows at that time and I had a run of 10 college shows in the Midwest and so

this audition would have been during one of the colleges I canceled the college which was probably about $1,200 which was a lot of money for me back then. And I booked a ticket in the middle.

So I flew out to the Midwest, did four shows, flew home to New York to do this showcase, and then the next day flew back out to the Midwest to finish the tour. And I get to the club, and Barry Katz is there, and he goes, no, no, no, you're not on the lineup. And I was like, Barry, I just flew in from the Midwest to do this showcase. Sorry, pal.

And Jason's just standing there like, I don't really remember. And I was like, I don't know. The club was kind of dead to me after that. I get that. And I mean, he had so many of his own clients, I'm sure that he wanted to throw on. I mean, it was incredible who he had at the time.

I mean, every night at that place was Chappelle, you know, would come over. Daryl Hammond right before he got Saturday Night Live was there pretty much. nightly and then it was um i'd have to look at the list but brewer right before he got saturday night live and then um patrice it was not a good club it was no it was next to the cellar which put it on the map but it was a lot of drunks um it was always one quarter filled it was like disaffected NYU students with you know um kind of urban people that didn't give

a fuck about my style of comedy. I didn't, you know, I just didn't, I didn't love the Boston. The weekends were packed depending on during the week. I will never forget, sorry to name drop so much during this. I didn't know we talk about this, but I'll never forget that summer. I think it was 95 when Chris Rock had just, he had left SNL and it was before bringing in the pain. And he was, I had no idea. He was basically being Rocky and going to every single club. Yeah. To get stage time. Even the ones, I couldn't believe he wanted to get on stage. at the door guy and he's like, can I get stage time? And I'm like, you're Chris Rock, of course.

And he went on and it was like what you were saying, a Tuesday might have been 12 people in there, maybe something like that. And it was purely, and he talked about it later, just he was going to any club he could. The, you know, the Carolines are like the lowest, the lower ones. Not that the Boston was the lowest or lower, but he would just, to get in from any crowd. And then I saw his special and I'm just like, oh my goodness, he was Rocky. Well, dude, at that time, he was telling me at that time, his agent dropped him, his manager dropped him, he couldn't get arrested.

Like, his career was completely stalled out. And I think everybody watched him. And the thing about Chris Rock is, like, he's one of the best comics to ever do it. But he's not like a Chappelle. Chappelle walks on stage, and he could read the phone book. I mean, that guy is so funny. His style is so good, his confidence. Chris is not that kind of comic.

He goes up with new stuff, and it does not go well. And then he's a craftsman, and he puts sweat, blood, sweat, and tears into it, and he turns that material into brilliant material. And the confidence comes, even now, I see Chris do new material, and it's just not the same as watching Chappelle do new material. It's incredible. I mean, I opened up, I can't believe, I never thought I'd be talking about these stores. I had a sketch group.

we opened up for Chappelle. This would have been like late 90s, maybe two, right before he got his Comedy Central show, we're at James Madison. And they're booing us as an opening act even before we say anything because they just want to see Dave Chappelle. Contractually, the guy has to do 90 minutes. He's doing two shows. And the first one, I think he did two hours. And the second show, and I'm not exaggerating, was three and a half hours. I mean, he. And how old is he at this point? Oh, goodness, in 2000. I don't know. I mean, probably like late. 20s maybe maybe he's 30 and he's reading out and it gets to the point where he's just reading out of like his notebook and getting as many hard laughs as he was getting with prepared material

and the guy was unbelievable and I remember afterwards he was very very nice he hung out with us and he's like don't I know you I'm like yeah he used to be the door guy at the Boston he was very very kind yeah to me but the evolution no he would be I remember he'd live in like union square in that building and he would just show up to the Boston without doing any prep I remember seeing him in the fountain at Washington Square Park the summer of 95, just doing like a pop-up thing where nobody really knew who he was at this point. And he's just holding court and stuff. The guy was unbelievable, but he would just kind of show up and wing it and kill. Well, his hero was that guy who, who that's how he started was in Washington.

Charlie Barnett. It was Charlie Barnett was. And, like, he was very tight with Charlie. And he really was like, Charlie was like a role model for Dave. Yeah, he wrote a screenplay, I remember, around that time Dave did that never got produced called King of the Park or something like that, where I think, I think maybe he wrote it or somebody, but there was talk. Maybe he'll go back to it and stuff. But now, watching Dave, I mean, I have to, I do have to say from 95 until I saw him at James Madison, he was almost unrecognizable in terms of the, he had the same great persona and point of view, but in terms of his material and in terms of like his just ability, I just was below. away. I mean, that all happened. I mean, after a couple of years and stuff, because when I moved to New York, everyone's like, this is going to explode. But it took him a while. And I mean, if people watch a very first letterman, I remember watching it, he did okay. I mean, I remember Jeff Ross

blew the lid off the place soon after, right before. There were Ray Romano. They just did okay with it. And I was just like, this guy, maybe he needs a little bit more time. And it did take him a little bit more time. I mean, he was always really, really funny, but I think to maybe to get to where he needed to be Dave Chappelle, he just needed a little bit more time, which I don't think people really talk about. But when I saw him in James Madison, I was like, who is this? This is Superman. And right after that, got this Comedy Central show and just absolutely exploded. But I do want to segue into Letterman. You are the only person to my knowledge that was hyperventilating backstage before their Letterman appeared. Yeah. Now, can you talk about that? I have hyperventilated

on stage before. I mean, I haven't hyper than in a long time, but when I used to go on stage, I did it before the show. I would do it sometimes even during. It's a very scary thing. This is going to be, you think, it's going to be your very first letterman appearance. This is December 19th, 1995. Jack Lemon is also a guest. Where are you when you start hyperventilating before the show? Well, actually, the Jack Lemon show I got bumped from. I got I got bumped three times before I did my first appearance. And Jack Lemon was the one that I really didn't begrudge at all. I was such an honor to be backstage and to watch him,

and he was on fire, and they gave him an extra. The one I was on was with Faith Hill. And so I was backstage, and I've been running the shit out of the set. And Zoe Friedman was coming around the city with me. Robert Morton looked at the set. Everybody looked at the set a million times. And I had gotten it because I was at the shit. the Montreal Comedy Festival.

And I kind of like had a crazy experience up there where I went from a completely unknown comic in New York, in the trenches, doing spots. And then I got red hot at the festival and I got a huge six-figure development deal with Fox. I got booked on Letterman. I got a show on the USA Network. I signed with an agent.

I sign with a manager. And then I, so then I come down to the city. And I do the set. And now I'm backstage and like, I've only been doing comedy about seven years at this point. I was backstage and I had complete imposter syndrome. I could see Letterman through the curtain. And I'm waiting to go on and Biff Henderson is standing there. And he's got his hand on my shoulder.

And all of a sudden I just start to, yeah, I started to hyperventilate. And I started and I just had to stop. And I thought about my dad. My dad had just died. And he was my biggest fan. And he meant a lot to me. And so I kind of talked to my dad, you know, like, we did this, we're going to do this. And then somebody once said to me, pretend you already killed before you go on and then go on.

And so I said, Dad, we already killed. So I go on stage. I got one laugh and then the universe just opened up. And I felt like I was standing on stage at Stand Up New York on a Wednesday night. you know, the bass player made a noise at one point and I reacted to it. I was like, I was reacting to the crowd. I was grounded and I had this set

that I'd run so many times. It just, I just killed. And it was material I was really proud of. And then Letterman came over and he shook my hand and he said, really great job and it was very complimentary. And then I walked off stage and it all hit me. and I just started crying. I was like hysterical.

And Faith Hill was about to go on. And she just came up and she wrapped her arms around me. And she's tall. And so I just had my head on her shoulder. And then I walk out and I saw Zoe Friedman and, you know, she and Eddie Brill and they were all just standing there like, that was amazing. And yeah, and then I had an after party at the Friars Club

with my whole family that was in the audience. You have another distinction. I may have only heard this one. or two other debuting comics, if that, and this was, I believe your debut was January 4th, 1996, is that after your set, your first time that you went on, didn't you actually see Dave in the stairwell? Yes. That doesn't happen almost ever for the guest. No, no. He doesn't want to see anybody after that show, unless they're a race car driver, or if their last name is Miller, Erdreason, or Altman. Well, yeah, they go out of their way. They tell you,

You know, don't be in the hallway when Dave comes through, and then they have a PA come through the stairs. Clear the hallway, clear the hallway, everybody out of the hallway. So, like, we all run in the green room, and then he comes out. And then I go to my green room, and I'm hanging out with Michael O'Brien, who is my publicist, and my sister was there. So we're hanging out for a while. And then I leave, and I go walking down the stairs,

and Letterman must have had a meeting or something. so we walked right into each other and I said oh hey Dave thanks for having me on the show and then he just said the same thing he said to me on stage he was like uh fantastic job great to see you thanks for coming by and just kept on walking and I was just like oh that's I mean just to be able to kill like that when um I mean the show was always I mean such a big deal for comics but back then Dave was still you know I mean by that point maybe you Jay was beating him a little bit, but, I mean, it was still, to go on that show as a stand-up, I mean, it was such a huge, huge deals.

There's huge, yeah. You did something like four lettermen's, and I know that, yeah, you got that Fox deal and got something like 300K or something. Back then, I mean, if you do the inflation, I mean, back then that was a lot of money. Now it is, but crazy money. And then I thought this was really, really funny. The first time that you are flying first class, your life changes. I've had this happen before

and I just thought it was really funny that you're sitting in first class and the person next to you is trying to talk to you and you just don't want to talk to them and finally they ask what you do you say, stand up, what do you do? And you're like, they say I'm an actor. And what do you say?

You said if I know you in anything? I go, what have you done? I go, what have you done? And then he goes, I won an Oscar. And I said, oh my God. And then he just goes, John Voight. And then he shakes my hand. And I was like, because first of all, John Voight does not look like John Void anymore.

You know, his look changed at a certain point. And he's one of the great actors of all time. And so we started talking. And it turns out he was flying back to New York because his father was on his deathbed. His father was a greenskeeper at a country club in Westchester. And my father had just died. And we started talking about our father. fathers and we talked for five and a half hours for the entire and all I wanted to do on that

flight was sleep because I'd been out all night and but I at the end of it we exchanged numbers he gave me his address which was weird and uh he said let's keep in touch but then I never did because I just felt like you know it was a perfect interaction with the guy who I had so much respect for and I didn't want to ruin it I didn't want the next interaction to suck or for it to be like, that was weird. And so I never reached out to him. And then probably seven or eight years later, I was in Indiana. I was on the Bob and Tom show, which was the biggest syndicated talk show in the country at that point.

And so I'm sitting in with them. And then they said, hey, do you mind, by the way, John Voight has a film to promote? He's going to call in and just do like a quick 10-minute call in. I said, no, of course not. And I said, I actually have had an experience with him once. And so he calls in and they go, by the way, we got somebody in studio that maybe you remember Greg Fitzsimmons. And he goes, Fitz-Dogg. And he remembered me.

And we talked for a while and he was very warm. And, yeah, it was very sweet. That's incredible to have that. Because when you're famous like that, people are coming up to you all the time and you meet so many people. That's amazing. Yeah. A lot. When you were the warm up at politically incorrect with Bill Maher, what year was that and what was that experience like?

I think that was 96, maybe 94. It was before your Fox deal, obviously. So maybe like 94. I think it was, it happened right before Montreal. I remember that. And it was, so I was living down on 25th Street on the west side. and the show was up in the 50s on the west side. And so I used to rollerblade to work every day as the warm-up.

And so I would go to a red light and I'd wait for a delivery truck, like a UPS truck to pull up. And then I would hold on to the back of it. And I would get pulled up 10th Avenue. And the trucks usually were in sync with the lights. So I would sometimes take one truck ride all the way up into the 50s hanging out with my rollerblades. And so, and then I'd go, and I would do, you know,

and Bill wanted you not to do crowd work. He wanted you to do material. So I would do material and I would mix it up. And then one day I got called into his office and he said, how would you like to write for the show? I love your material. Didn't have to put a writing packet together, nothing. And I didn't even have an agent at that point.

So I said, yeah, amazing. And so I came in and I started writing with these guys, you know, Hayes Jack, and uh and and Chris um Scott Carter Scott Carter was there yep and uh Danny Vermont and Eric Weinberg who's now in jail for rape and he was my office mate and uh we used to we used to start the morning off you'd get to work this is before the internet so Danny Vermont no hotchkis named John Hotchkis used to put together the Hotchkiss report which was a list of, he'd put down a paragraph for all the top stories in the news.

And then you had until 11 o'clock to write 40 jokes. So you'd crank out the 40 jokes. And then you'd go into meetings and you'd talk about the show that day who the guests were, what the topics were, what their opinion would probably be. And then you go off and you write jokes for Bill. You'd write jokes for the guests. And then you'd go to the taping, see what. which of your jokes got picked, and then, uh, and then there'd usually be a meeting after the show where you talked about the next day's taping. They didn't make you do warm up when you were a

writer, did they? Because sometimes on the show is the, the writer will still go out like Mike Sweeney or whatever for a while or Brian McCann. No, they replaced, they replaced me, I think, with Danny Vermont when I, when I stepped down. So this is the CBS broadcast center. So how, how long were you a writer and what led you to leave? I think I was there for, for two when you're a writer you get you get cycles

of 13 weeks and so and then they have to renew you after 13 weeks so I made it to the I was at the end

of my second cycle and then I got fired he basically you know it was nice was I mean apparently that happened a lot

it was very rare they'd bring in writers and if they fit it was a very intellectual show and it was a tremendous amount of work and some of the guys

there were Harvard guys and it was like that level of writing and I was still going out every night and doing sets until one o'clock in the morning. And then the Montreal thing happened so I missed some work and I was a little distracted. So I don't think he saw us, but what was great was he came in the room. He could have had Scott Carter let me go. Believe me, I've been fired from other writing jobs and it's usually not this ceremonious. He came in and he sat down and he said, I wanted to be here because I want to tell you you did a really great job. I don't think you're 100% right for the job, but, you know, stay in touch and blah, blah, blah. And so it was very, I thought it was very classy the way he did it. I love the fact that you've had so many

experiences in late night and just, what was it like being at the Friars Club when you were a kid just because your dad was famous. If you were on, he was first of all, he was the host of Good Day, New York, and then he's on the radio. And back then especially, you were famous if you were a local person like that or especially a major city. So you're going into the Friars Club. Do you know that when you meet Milton Burl who Milton Burl is? Can you appreciate this? Oh, yeah. I mean, I was raised on comedy. My father loved comedy. I collected comedy albums. I used to watch The Tonight Show with him. And I, you know, my first concert ever was Steve Martin when I was probably 10 years old. and I memorized all of the albums.

And so, no, I was very aware when I met Milton Burrell and Hennie Youngman and Alan King. And then there was the guys that were more Catskills guys that if you were in New York, you knew them, but maybe not nationally, but like Freddie Roman and Dick Capri and Mousie Lawrence. And so those guys were, they really looked out. They loved my dad. My dad was the one Irish guy in a club full of Jews. and he really just like, he just made them laugh. They loved his energy.

He was just, he was, he had more charisma than anybody I've ever known in my life, my father. So those guys really looked out for me. And then after he died, I joined the club. Freddie Roman was my sponsor and I joined the club. You know, it was a second family to me, all those years that I lived in New York. When your dad for over a decade was doing the Jerry Lewis Hellathon, did he have any interaction with Jerry or it was just they would cut to the local the local around the country and stuff or did he actually

work with Lewis ever? No, they would go out to Vegas once a year they had a convention in Vegas for a week and my mom used to go with them and they'd see shows, they'd see Sinatra because my father knew Sinatra because that's the number one guy that his radio station played. I mean, they weren't tight but like he, you know, he knew of my father and when he came to Vegas he'd put him on the guest list and so they get treated great. My mom had a fur coat, and so Jerry would meet with everybody.

And, you know, my father wasn't a huge fan. I think Jerry was not known as being, he was a little narcissistic. Let's just say that. Back in New York, you're 14 years old. You're with your dad at a comedy club, and there's a future, there's a guy who's going to be, went on to do Johnny Carson numerous times. Johnny loved him. You're talking about Kevin Meaney?

I am, and he was the waiter. Yeah. He was, yeah, yeah, yeah. No, no, no. It was my father belonged to a golf club in White Plains, New York. And so there was a diet, you know, he would eat in a dining room three nights a week with my mother and with us. And there was a waiter who was very funny. He had the, he had on the red waiter jacket and the black bow tie, which he ended up wearing as a comedian for his entire career. And he was, he would come over to the table and he would do routines. He was only, you know, probably. He was probably 17 or 18 years old himself. I know, maybe a little older because, yeah, I was 10, and he's 10 years older. So he was probably 20 years old. And he would do all these routines like, would anybody like dinner? We have the New York cheesecake tonight. The cheesecake boats are coming.

And he would sing this whole song about cheesecake boats. And he would dance around. And my father just loved this guy. He was so, they used to laugh. all night. My dad, my dad, my dad would mom would stay there until like two, three o'clock in the morning. And so when Kevin first wanted to do stand-up, my father encouraged him. My father got him on at Catch a Rising Star in New York for his very first appearance ever as a comic. And over the years, you know, my father always told me later, he goes, you remember that funny comedian from

Nolanwood, Kevin? I go, yeah, of course. He was hilarious. He goes, well, he's a big comedian now. And you should look him up if he ever comes through. I was in college in Boston. I had started doing stand-ups. So my father was like, you should look him up if he ever comes through town. So I go out to Catch a Rising Star. It's like 1988, and I see Kevin,

and I've never seen a hurricane come through a comedy club the way his performance was. He had, the place was absolutely packed, line of people trying to get in outside. And he goes up, and I mean, he is sweating and he is dancing and he's singing and he's doing his voices and his mother's and I mean people are every time I saw him not every time because sometimes he bombed but in his

prime people would be doubled over they couldn't breathe their stay was like not some people everybody was like that I've never to this day I've never seen anything like it so the crowd files out I haven't seen the guy since I'm 12 years old And I'm waiting around, and he comes walking out, and I look at him and he goes, Fitzsimmons. I go, yeah, great Fitzsimmons. He goes, I remember you, account number 236. So at that point, he kind of like, we started to talk, and then he would bring me out to open for him on the road. He gave me a lot of advice.

I would stay at his apartment in New York. And he really mentored me for a lot of years. And that kind of transitioned into like a true friendship where we got so close. that, like, he was in my wedding party. I was in his wedding party. He ended up marrying my next-door neighbor, who was my babysitter at the time. And not at the time when I was younger.

So, yeah, and then, you know, his daughter is my goddaughter. And, you know, it was really a very, very special relationship. I love hearing that. How do you go on Chelsea Handler show Chelsea lately 40 plus times and not feel pressure? Did you feel pressure? New material?

I mean, I'm guessing that they had some writers that were writing for you, but just to be consistently funny for 40 times and then do stern something like 50 plus times. How much pressure is that? And how did you generate the material? Well, I started out, you know, I was an English major in college. I wanted to be a writer. And my father gave me advice early on when I decided to be a stand-up comic instead of a writer. You know, I wanted to write books.

And he was like, he's like, just keep writing. He goes, that will always keep you in this business. If you're a writer, you will work. And so I always took that to heart, and I always had new material as a stand-up. And then I started getting these shows like Best Week Ever, which I did on VH1 for five years, where every single week they gave you a list of topics,

and it was like Hotchkiss's Hot List. They gave you just a little brief thing, and then you'd write jokes. And so every week I'd go in on a Tuesday or Wednesday, and I would have pages of jokes written and then you would just do them for the camera and they'd cut it up and then I did the same thing on I love the 80s, I love the 90s,

and then so I kind of had pretty good skills as a short pop culture writer and then when I came in on Chelsea lately I had already written on a bunch of TV shows at that point. I started writing for TV in like 2000 when my son was born to kind of get me off the road a little more when I did Chelsea Lately

nobody ever wrote a joke for me on Chelsea Lately I wrote every one of my own jokes but there was a guy there that was very helpful Ryan he books the Tonight Show now so anyway he would look over my jokes and he'd kind of guide me out what he thought would work

or sometimes another comedian had the same joke so I'd take it out but then and then it was a lot of just like you know shing on Chelsea shit on Lonnie Love, she got Joe Koi. You know,

they really liked it better when there was interplay. And a lot of times when I was on, we would only get to a couple topics because there'd be so much just roasting each other. It's incredible how many appearances you were able to do.

Did you ever think in a million years when you asked Howard Stern to write your forward to your book that it ever would turn into any complication other than you say yes, you say no. But this thing just took on the life of its own. Talk about holy publicity for a book. How did you feel, though, and what

happened? Well, so I asked him to write the book. You know, and we were pretty close. He'd invited me to his house in the Hamptons, and we regularly texted each other, and I did the show like 50-something time. He gave me my own show on his channel, which I did for 10 years every week for not a lot of money. And you were almost artist. Lang, too. You were the second runner up. So, I mean, you were very, very close to that gig. Yeah, I almost became a part of the show. So I asked him to write the forward. And I wrote in the note, I gave him an out. I said, if you don't have time, no sweat, no pressure. And then he read the note on the air. And then they called me. And he said, blah, blah, blah. And I go, okay,

you don't have to do. No, I didn't say you have to. He goes, he goes, I'll do it. He goes, I'll do it. He goes, I'll do it, but I don't want to do it. And I said, okay. And then he started talking about me, and they're like, how could this guy, I don't know this guy? How could he ask me to write his forward? You know, it's just, I get, I'd rather be having sex with my wife. I'd rather be playing online chess, blah, blah. So anyway, he calls me up and he goes, Greg, just let me off the hook. I go, Howard, I didn't put you on the hook. I said, I wrote you a note, gave you an out. You said you'd do it. If you don't want to do it, just say you don't want to do it. He goes, no, you got to let me off the hook. I go, no. I go, you're a man. Take yourself off the hook. And so that turned

into the conversation. And it was a bit, but at the same time, it started to feel real. And then I would email him. And I'd be like, Howard, uh, I know today you were kind of yelling at me and blah, blah, blah. I go, I just want to make sure, are we good? And then he'd write back, oh, completely. Yeah, we're totally good, you know, uh, you know, then the next day on the air. So Greg writes me this email. Are we good? And then it would turn into a whole other thing. And this went on for like four or five weeks, like couple days a week, getting called. I'm in L.A., so I'm getting called at like 4.30 in the morning to talk to him. And he ended up writing it, but he just dictated it on the air. It was not, in the end, it was not a good experience. And my book came out the same week as

Baba Booie's book and Adam Carolla's book, which were my two biggest places to promote the book. So in the end, I don't know how much it really helped. The book did well. We went to paper, you know, we ended up getting a second edition and paperback, but you know, it did not, I don't look back on it as a good experience. I'm so sorry. You just never know. You know, you think you're giving the person that out. I have to ask you, you were supposed to be on the Tonight Show when September 11th happened. Now, how does this work? Do you, I mean, you know the show isn't going to happen, but the Tonight Show still

call you to let you know that the taping's going to be canceled? Or how does that work? How soon did you hear? Or do you just, do you don't get the call? And you're just like, I know this isn't going to happen, but does you get a call? Yeah, yeah, yeah. There was, there was a call. And, you know, it was a quick call. You know, I was expecting it. And, you know, that was weird. And, you know, my mother was actually on a plane she was she was supposed to take off at nine a m from jfk to lax on september 11th and so i'm sitting at home and i'm watching these planes going to the bill and all i'm thinking is like is that my they didn't tell you they had no idea which planes these were and so i spent about three hours waiting to hear from my mom that she was okay and she

basically uh they they just got everybody off the plane as soon as they could they told them to just get out of the airport don't they said if there's a taxi if there's a bus get on it just get away from the airport so my mom who lived in westchester took a bus to long island with without her luggage you nobody got their luggage just go and uh she called my aunt when she got out to long island who was like 45 minutes away she came and picked her up and uh And she kept saying, I remember she kept saying, well, I'll come out tomorrow. I'll come out tomorrow because my son was like a year old and she really wanted to see him. And then she kept doing that for like a week.

She stayed at her sister's house. And she kept trying to come out. But obviously no flights left for a couple weeks after that. Yeah, I mean, I was here in New York when it happened. I mean, talk about surreal. I was going to ask, what was it like doing Letterman show when a guest host Bonnie Hunt filled in for him? because not a lot of people can say they went on with a guest host. And there were only, you know, there weren't a lot.

But what was that like? Wow. I don't even remember that to be. I mean, I vaguely remember that. But I'm sure I was disappointed. Obviously, you know, you want to be on there with Dave. But I remember they had a, who is the guest host? Oh, Janine Garofalo was a guest host on Letterman one time.

I was there. No, I was there. I mean, I just left the show. I would add a day job there, and I was there in the audience in the balcony. Yeah, it was her and Gallif. No, it's when she guest-hosted that Gallifinacus made his network television debut. Yeah, yeah, yeah, because he killed. Zach wanted to come on the show and Letterman wouldn't let him on the show.

Neither would Conan. Neither, Conan wouldn't? Nobody would book this guy, and then he kills, and then very soon after I heard the Conan Booker was at, can we see some videotape of the letter of the Janine? Right, right, right. So, yeah, the guest toast thing can be a good thing sometimes. When you were writing for Ellen DeGeneres, do you have any, I know that you've talked about, and a lot of other people, it's been, it was a challenging time at the show with her. What are some good memories that you have early on with her? Do you have good memories or have you blocked them out?

Oh, yeah. The show started great. I mean, I think it got tough. It definitely got tough later on. There was a lot of crying. There was a lot of quitting. There's a lot of firings. There was a lot of tension. But the first six months were. great because I think she was very excited to have a show again. She was in a big down cycle in her career. Nothing was going on. And she got this show and she was really a show that she wanted to do. You know, she, she really was grateful to the writers and we had a lot of fun. It was very silly. She's, she's a funny, silly person, you know? And we used to play ping pong. She had a table outside her office that she was pretty good. And so she and I were very competitive playing ping pong with each other. And I would do this thing where if I slammed it and it went past her, she would have to go and get the ball. And I would say, go over and pick up the ball. Keep walking.

Keep walking. There you go. Bend over. Pick it up. Look what I did to you. And all the writers were watching. And she'd be laughing around off. And so, yeah, we had, we were very close, I feel like, for a while. And then it sort of faded at the end. The show was good right away, which does not happen almost ever for a late-night person. This was daytime, but just to have a talk show, Rosie was good right away, Rosie O'Donnell. It's very, very rare. When you were doing the warm-up, because you started as the warm-up, correct? No, no, no.

I came in as a writer. You were a writer, but then didn't you do warm-up on the show? Yeah, they basically, they were doing some test shows. And, you know, so they had an audience and we did the show as if it was real. This is, you know, a couple weeks before the show aired. And so we practiced the show. And then the producer said, Mary Connolly said, Greg, jump up and just do the warm-up, warm up the crowd.

And so I did. And we did that for like three or four test shows. And in the meantime, Ellen was looking at tape after tape after tape of different warm-up people. She didn't like any of them. And so the day before the first show, Mary says, Ellen wants you to do the warm-up. I said, I'm not doing warm-up. I'm not doing audience warm-up on a daytime.

talk show. I'm a writer. And she goes, well, it'll pay an extra $3,000 a week on top of your writer's salary. I was like, yeah, I'm good. I can do that. And so it was literally like the easiest warm-up job of all time because these crowds came in and they were frenzy. They were out of their minds. And so I had to warm them down. I literally went out there for 10 minutes and just said, all right, Ellen's going to come out. No yelling out. Blah, blah, blah. Stay cool. I tell a couple jokes and then, uh, and then that was pretty much it because they had a DJ that would play music between segments. So I didn't even have to do anything there. So I would do that and then I would sit in the front row with cue cards and a magic marker. And during the show, I would

write out joke, we already had written jokes, but then I would write out jokes on the fly. Like if something came up, she was interviewing a guest, I would write down a quick line and I'd hold it up. And so, I did that every day on the show for two years. Mary was Mary Connelly, the producer who worked at Letterman. So at what point, what triggered you to stop going to the production meetings? Was there an incident or was it just a buildup? Well, I always went late. I was always late for the meetings.

And when I came in, since I would always be late, I decided you can either slink in and feel embarrassed and shameful. I decided to go 180 degrees different And I would walk in And there was a guy named Derek Westerfeld Who was the executive from Telepictures He was the only guy that wore a suit Suit and tie

He was a little stuffy And so I would walk in And I would go Ladies and gentlemen Derek Westerfeld And then I would go Dan, dun, da, da, da da, And the whole room would join in

And everybody would do this chance. And by the time the chant was done, I was seated in the corner, had my computer open, and I was ready to go. And we continued the meeting. Hilarious. Yeah. I know that this was after you, but Karen Kilgareff was the head writer. And I think this is important for me to say something. And to your knowledge, and if you don't know, you don't have to say it. But I know that the press has said that, you know, it was during the writer's strike. And you weren't there anymore. that Ellen had fired her for some reason for apparently the press, what they said is because she wouldn't come back to the show when it was on strike.

But it was the opposite to my knowledge. And I heard from a very good source that it was because Karen was not thrilled that Ellen was doing shows. And, you know, she was, I think she was WGA. And that was kind of like the turning point of their relationship. Do you have any knowledge? If not, we can kind of. Well, I mean, not necessarily.

I will say that, you know, Ellen was absolutely a writer on the show. She was WGA. When we won Emmys for writing, which I won four, she won Emmys with us. She was on the stage taking a trophy as a writer on the show. And it is absolutely forbidden for a host who's a writer to write for their own show. And then there was producers, from my understanding, a lot of the producers were writing material for the show as well, which if they're not in the writer's guilds, You know, if it's a Writers Guild show, the only material written for the show should be from writers

that are signed as members of the WGA. So they were one of the only shows that continued on during the strike. And it was shameful. And I was gone by then, but I was embarrassed that the show would do that. Gary Shanley said being on TV every day is just not good for you as a person. It changes you for the... Do you think just the pressure?

It was the pressure that just got to Ellen, if you had to guess. I mean, going out there and being consistently funny like that is not, if you have any, especially she's mentioned,

she had some, I don't know, I don't know, post-traumatic stress or whatever. It's just not a healthy thing. Do you think that that may be contributed? It just, like it was once a week like Dennis Miller

and might not have been like that. Yeah. Yeah. I think it is a lot of pressure because I saw it from the beginning. And, you know, you're not just hosting a show

and having to be in a good mood and present. and you're also involved in the writing of the show from the beginning to the end of proving every joke. You're also meeting with wardrobe to get your outfit. You're meeting with hair, getting your hair done. You're doing promos for the show with local networks for another hour. When the show is done, you're overseeing hiring and firing.

It's like being the CEO of a company and then having to be charming for an hour on top of that. It's a lot of pressure, and the people that do it well, I have a phenomenal amount of respect for, you know, people like Conan that, you know, without exception, people that work for them say great things about them. And there's not too many of those hosts that are around that Kimmel, I think, is like that as well. Yeah, I absolutely took a toll. I want to talk about your YouTube special You Know Me, which is approaching 500,000 views. Let's get it there, people. click on it you know me mom you you listen my mom yeah listen some other wonderful people and stuff but this special this was done in texas and how many specials have you done now i'm not a big special guy i've only did i did two different half hour specials on comedy central and then i did uh an album

and then i did a special in tarry town new york for comedy central that then went on netflix for a long time and then this last one I just did self-funded on YouTube. So, you know, for 35 years in the business, it's not a lot of specials. I don't know why. I guess I was writing a lot on TV shows, so I wasn't as focused on coming up with a new hour every year the way a lot of people are.

But now I'm in a role where after doing this last one, I'm really hungry to do another one. People loved it. I mean, it's a good length. And, I mean, you look at the YouTube comments. and stuff. I mean, yeah, let's get, let's get more reviews. Did you ever do, I mean, you've all these podcasts, but Fitzdog, definitely, I mean, you were doing, you've done so many episodes. Was there any episode that a public, public figure asked you afterwards, please don't

air this? Like, I know Neil Brennan, the first time told Mark Meran, I don't want you to air this. Was there anybody that ever did that in a thousand plus episodes? Good question. David Fincher also was another one with Marin that said, that recorded this said, I don't want this aired afterwards. There was, uh, I got into a fight with, uh,

Rob Cordry's brother. Nate? On the podcast. Nate, yeah. And he came on and he was promoting something. And, you know, I know Rob so well. And I knew the family that he came from in the sense that,

you know, they're Boston Irish. They're Catholic and they're wise. And they bust balls. So me and Rob just have so much fun shing on each other. And so I almost felt like, I never met Nate, but I sort of felt like I must, it must be the same guy, you know. And so I said some thanks to him and he was not hearing it. He was not having it.

And we went back and forth and it got kind of nasty. And then there was sort of like a little bit of a Twitter war afterwards, minor. It wasn't a war. It was a shoving match. And that was the only, that's the only time I've had to get. where I really feel like they regretted coming on. And I've always felt bad about that because I respect for Nate. I think he's a really good guy. I respect his work. And I think it was just a tonal. I think it was obviously my fault.

I had the wrong tone going into it. And it just didn't gel. It's going to happen. A thousand plus episode Sunday Papers with Mike. You've been doing so much when you were with Stern. It's incredible how much you've done. I mean, just episodes. Do you have a dream guest?

Maybe Dave Letterman. Yeah, well, Mel Brooks, but, you know, I don't know if it'll happen. Have you tried? Yeah, he actually, his son lives in my neighborhood. Max. Yeah, Max lives in my neighborhood. So I wrote a note to Mel, and I dropped it into, which was kind of obnoxious, because I don't know Max. And I dropped it in his mailbox.

And I said, if you can give this to your phone. father for me. And I got a note written to me from Mel Brooks, from his stationery, from his office, and it was kind of like a couple paragraphs saying he appreciates me reaching out, but he would feel strange about doing something in his son's neighborhood because my studio was at my house at that time. And he graciously declined. And, you know, I still have that note. That's Mel Brooks. At least you got a note out of it. Yeah, I know. It's amazing. Everybody that you've gotten on your podcast, thank you for. doing this, is it okay in like a year to ask you to do it again? I don't want to, I know you don't

do these. Of course. Yeah, yeah, yeah. Hit me up in a year and then I'll be busy for five months and then we'll do it. I know that people with their own show, sometimes it's tough. It's just being on the other side, but how did this go for you? I felt really good. I love that you did all the research. There's things that you said that I was able. I completely forgot about the 9-11 appearance on the Tonight Show. I forgot about Bonnie Hunt hosting. So this was informative for me as well. Now, I really, really appreciate you doing this. So, yeah, we'll talk in a year. All right. Sounds great, man. Thanks for having me.

Thank you. Thanks for listening. Please subscribe so you never miss an episode. On Apple Podcast, please rate it and leave a review. Be sure to go to late-nighter.com for all your late-night TV news. And you can find my podcast at Late Night. dot com forward slash podcasts have a wonderful week and i'll see you next tuesday We're going to be able to be. I'm going to be.

We're going to be. Thank you. Thank you.