Inside Late Night with Mark Malkoff - Jon Rineman

Episode Date: November 5, 2024

Jon Rineman joins Mark to discuss his 9 years writing for Jimmy Fallon, meeting Doc Severinsen,  & writing jokes for Jay Leno's Tonight Show and SNL's Weekend Update.   Buy Jon Rineman’s book: The Garden’s Always Greener Official Website: www.rinemania.com   Follow on IG: @rinemania Follow X/Twitter: @rinemania

Hi, I am Mark Malkoff and welcome to Inside Late Night, presented by Late Nighter.com. Today's guest is John Reindman, who for nine years wrote for Jimmy Fallon on Late Night, as well as The Tonight Show. We talk about his time at Fallon, meeting Doc Severnson, writing jokes on Leno's Tonight Show and S&L's weekend update and more. Now it's time to go inside late night. John Reinman, thanks for talking with us. Yeah, thanks for having me, Mark. You know, I got to say, I was such a fan of the Carson podcast.

I came along, I think towards the end and went back and listened to them all. And so this is really cool. This is an honor for me to meet you. Oh, my goodness. Thank you for having me on. Yeah, for someone that wrote for Fallon for nine years. And you've done so much in your career. You wrote a very famous joke for the White House Correspondence Dinner that, you know,

looking back in history, people still talk about. there's a lot to talk about. I do want to mention one thing. I was on your Instagram and I saw that and speaking of Johnny Carson, there's one person I've gotten to talk to on the phone many times and that is Doc Severnson, but you actually got to meet him at Fallon. Yeah. What was that like? It was awesome. It was surreal in that he still just looks exactly like Doc Severnson. And he dressed exactly. I think he just had his farewell performance. I think he just retired from the road, But he was still hitting them every night when I was there. And when we would go out to L.A., which I loved.

I absolutely loved going out there doing shows, especially in the winter. It was, you know, reinvigorates you when you go out there and you get the palm trees and the history and everything. I just turned to him and I said, Doc is here, you know? And then he kind of said, yeah, I got that a lot. And I just took a picture, man. And he was great. It was so surreal because I think he's the only person. from the Carson Tonight Show that I've ever really gotten to meet that I mean I'm I apologize

if I'm forgetting anybody there may be somebody that worked there for a little while and they're going to say Ryan what the hell man but you know he was he was awesome he could still play and immediately sent it to my dad who was a huge Carson fan and and he wrote the same thing back right Doc is here tonight yeah Doc is here so yeah it was really cool I knew that he played in LA with the band when he when he was there was the photo taken in New York this one the photo was from LA he was there two years he was there in 2015 and then again in 2016 yeah he's amazing guy yeah yeah he was great you know it was it was definitely a generational thing some people were like what do you so get I was like you don't you get it man it's Doc Severinson like you know it's it's

doc from all the famous clips and you know they're fighting about what they're going to do for Thanksgiving and who's going to go over to whose house and why they don't hang out and everything. And it was just amazing. It's just so cool, you know, but we just talked about music, really. Like, we just kind of talked about, you know, we talked about Tommy Newsom and O'Shaughnessy and all those guys, because I'm a big music nerd. And so we really just talked about that because you only get so much time with somebody like that. Part of me wished I'd talk more about Johnny, but, you know, it's like a, he really knew his band. he knew the guy's in the band and he could really answer those questions and uh he liked talking about

Tommy quite a bit and so that was cool and uh with johnny it's like what is someone gonna say you know no one really knew him all that well but it was cool just to talk about the old tonight show band and and all that stuff so it was really neat he was awesome i'm glad you've gotten these opportunities so you're growing up in new hampshire you graduate from emerson in 2005 and you're home one night on a monday and your phone rings your dad's says somebody's on the line for you. And who is it? Well, dad told me exactly who it was. So long story short, we had a family friend who grew up with this person and they

were really good friends. And they, you know, for months, I had bothered him and said, man, you know, can you give me a break? Can you send me some, send some stuff to this guy and, and, uh, you know, help me out. And he just kept saying no. He kept saying, look, man, he's really busy. If you ever reads your stuff, he's only going to read it once. And I don't know if you're ready and finally I just went for it and said you know what I think I'm ready and so this guy our friend Barry said okay and he sent my resume and a cover letter out on a Saturday morning and then cut to uh in fact the calendar date we're recording this interview as a matter of fact mark was

October 24th uh 2005 and I'm watching the end of Monday night raw the go home and I'm not going to give that up so the house phone rings met my parents house just graduated from college I don't answer it. I figure it's my sister or maybe my grandmother calling for my mom. And, you know, whoever would call it 11 o'clock at night for a quick second. And there's a knock at my door. My dad comes in and he just kind of is looking at me like something happened. And my first thought was, what did I do?

You know, sort of that thing like the police are on the line or something. And he just says, it's Jay Leno. And that's it. Like, it's not Jay Leno's assistant. It's not someone where it's, it's Jay Leno. And I took the phone and, you know, I say hello. And then I hear, hey, this is John? And I say, uh, yeah, it's me.

Hey, this is Jay Leno. And, you know, my first thought was, you know, no, this is my buddy who impersonates Jay Leno. There's no way it's really him. And then I remembered, I am the one in the friend group that impersonates Jay Leno. So I couldn't be calling me. And so, um, it was him. And we talked for like 45 minutes and, um, mainly he gave me a lot of life advice in that time.

He kind of got to know me and, you know, the two things that he's quoted a lot saying in interviews, he said to me in that time on the phone, which were, you know, they pay a lot of money. So when they screw you, you have something left over. So, you know, live cheaply. And that stuck with me when I decided to stay in Astoria for all those years when people were trying to get big fancy apartments. And I said, no, I'm happy with where I am. And I'll order a cheeseburger when I'm out. I was out with Eliza Coupe and her family the other night. She was getting an award here in New Hampshire. And they all got nice stuff. I said, no, I'll just get the burger. I'm good. And the other thing was, don't go fall in love with a hooker, which sounds a little bit maybe dated. But that was Jay's way of saying, the people you meet in this business are people you meet in this business.

You're going to be friends with them as long as you're in the business with them, as long as you're working with them. As soon as the business is over, there's a pretty good chance they're not going to be your friend, not for any. reason that's mean or not for any reason that's hostile. But it's just it's show business. And when you're a showbiz friend and you part ways, you're not always going to talk. He said, your friends are the people that you're friends with now. He said, it's the people he went to college with. They're going to be your real friends. Maybe a few people you went to high school with. But those people

from your formative years are really going to be your friends. And he was right about that. I don't think I did as good a job following that advice. I know I kept all those friends that I grew up with. But yeah, I think like I made that mistake in the business in that, you know, when someone acts nice to you, you think it's easy to think,

they're my friend, you know, we're going to be friends for life. And then they maybe move on, do something else or you move on or whatever and you don't really talk anymore. And so the end of that conversation with him was, yeah, I'll give you a shot to send in some monologue jokes.

And, you know, he, he, no one ever left Jay's show. They all loved working there. So there was no turnover. And he was honest with me with that. But he said, I'll pay out of my own pocket. You know, it's, I own the, you know, production company so I can do that. And you're not in, you know, as soon as you're in the guild, you know, first of all, congratulations.

But second of all, games up, can't do this anymore. So just learn how to write some jokes for a little bit. And that's what I did. And I did that for several years for him. And it was, uh, it was a really great experience. How much do you think it helped? in the conversation you two bonding over the fact that you both went to Emerson? I think it helped quite a bit because he had already been told by other people that there were

some there was some resemblance and there were some similarities. But I think he knew that I felt as a writer frustrated the way that he had felt frustrated as a comic. You know, like when he went there, there wasn't a ton of stand-up. They were all kind of sketch people or, you know, eventually some of those people went on and performed. But it was it was all actors, and they all did dramatic performances and stuff. There was no one just going and telling jokes. They didn't really have comedy clubs at the time of Boston when he was there. And on my end, we had just gotten Facebook, which I don't think you could do status updates

yet. Blogs had not really even taken off. And so we weren't anywhere close to Twitter. So for someone like me that discovered this skill of writing jokes, of writing news jokes and set up, run up. punchline jokes, I didn't have anywhere to do it. And there were no programs at Emerson at the time. They were still in their kind of formative years. And even the facilities were being updated. So they had a place to go do this stuff and do mock late night shows and things like that.

And so I think he got a sense that I as a writer, I got more out of Emerson than he did for sure. Because I had a really good experience there. I really loved it there. And particularly my senior year in Emerson, it was as funny or as any way. could have, but still as a writer leaving, like I said, there was no social media, so there's no place to really take your jokes for a test drive. And when I told him that, I could feel him breaking a little bit, kind of going, okay, like, all right, yeah, you know, and saying, that's kind of how I felt as a stand-up. And okay, well, let's give this a shot. And so I think he had some empathy towards having a, you know, going through, getting the degree, having a pretty good experience, but being like, man, still don't feel like I quite have what I need. I don't know

where to do any of this stuff. And so he gave me that chance to really try it out. He had a professor at Emerson that told him he was never going to make it. And he, whenever he's been given an award from Emerson, I know that some students, I was told, went to the set in Burbank and gave him an award from Emerson. He just, he had to tell them the story about the professor. And it seems like it still bothers him after all these years. And I get it. Well, you know, Emerson, I can't go into too much detail, uh, because the last time he and I talked on the, I mean, I saw him earlier this year. And there was other people there. So it was more of a just, you know, hey, how you doing sort of thing. The last time we talked on the phone, I kick it into

too much detail. But I think they're sort of back on perhaps a strained relationship. Maybe it's been improved since then. But yeah, there's something with that. Emerson where they just kind of trip over their own feet when it comes to dealing with Jay. And I don't understand it. He's their most famous alum in comedy. I mean, whether they want to say, you could, yeah, I know they have Dennis Leary. I know they have Bill Burr. It's Jay Leno.

You know what I mean? Like it's a first ballot Hall of Famer comedian who hosted the Tonight Show. Things have changed, but there are a lot of schools. And I went to NYU and I put NYU in that group that they didn't have. have a lot of respect for the comedians. They really didn't for sketch and for any comedy. It's just, I've talked to a bunch of well-known famous people that went there and stuff. And it's been pretty consistent with people I've talked to that when they wanted to do comedy. And yeah, things have changed, though, which is great. I know, especially at Emerson, which is nice.

So you're getting one to two jokes on a week for Leno. You're 20. you're getting $75 a joke, which, you know, I mean, it's, you know, you're still getting your stuff on the tonight show. The confidence must have been incredible. And are you literally faxing the jokes? I'm literally, I'm literally, I'm literally faxing the jokes in. So when it started out, I would do it for my parents' house. My dad had a fax machine and it ran on the phone line and everything. And so it was just like that. It was very outdated. But I would use my, my parents fax machine and facts in the jokes. And Jay was honest. I mean, he said, one thing that shaped me, and I don't know that was for the, there's two, two things he said that that that night that as I jokingly call it funny ball. I may or may not be working on something that, uh, something else, uh, that has to do with that, uh, kind of telling the story, but I sort of had this checklist of what I would do every night to write jokes. And it got out a hand as down at the end of my monologue career, it got just way too crazy. But one of the,

a couple of things that I got from Jay were first come, first serve, meaning that the first time he reads the joke from somebody, that's the person who gets the credit for it. So that put in my mind, hmm, if I stay up until, because this is before Trump and everyone tweeting and mayhem happening 24 hours. So you could get ahead and write 10 hours in advance. And, be okay. You know, like George W. Bush wasn't suddenly going to become smart, you know, like quick or Dick Cheney was not going to become kind or, you know, John Kerry was not going to become exciting. You know, there was a pretty good handle on the news back then and what was going to happen. So I thought to myself, gosh, if I stay up till two and get my right, like say three pages, that means

as soon as Jay gets in in the morning, there's going to be three pages of jokes at writing that Faxter Trey that I wrote. And he would read him first. And that's how I got a lot of jokes on was just playing with the time zone and saying, you know, I'm going to stay up late and make sure my stuff's in early. And the other thing he said was, I remember him saying this thing. Yeah, I can't even, I can't even sleep. I can't put head to pillow until I write half my monologue the night before. And so that was a big rule for me too was I got to have at least half my jokes written the night before. So I would send a lot of stuff in and my dad was rightfully skeptical about my career choice. He was a Navy man and an airline pilot and had seen his industry crater after 9-11 and

he didn't want to see me go into something else that was very suspect and kind of shaky as comedy is. But faxing those jokes in really kind of helped rebuild and reframe my relationship with my dad because a lot of times I'd forget to clear out the fax tray. You know, it's late at night. You're like, okay, I'm done. These are off. And I still remember the fax number, by the way. He would, he'd go in the next day to do his work and stuff. And he'd grab the jokes and he'd read the pages of jokes. And he went from being skeptical to kind of being upset with Jay that he didn't use even more of my jokes. He was like, these are really good. And so he became like my biggest fan. And I told Jay that, that he called after my dad passed away. And I reminded

him, I said, yeah, you know, it's like that dad was my biggest cheerleader. And it's because he read the jokes, I was faxing in to you. But when I moved out and I was living in Boston, I would drive to Kinkos and I'd get there about 233 in the morning and they were open 24 hours. And Jay would I only take faxed and do email back then. Now he's mercifully moved on. So if I need to contact him, I can just send him an email. But yeah,

same thing, FedEx, Kinkos. And then when I was out in L.A., living in North Hollywood, same thing. Find a, you know, some place with a copy machine in the middle of the night. Sometimes it'd be like on a studio lot or something. If I was working as a PA,

just go in and hope I don't get caught sending this local facts, as silly as it may sound. But that's the way they did it. The term was faxers? Yeah, that's it. You were also doing this for Saturday Night Live when Seth Myers was there. And you've got, you've got jokes in not as many as Leno. Obviously, the show is 20 a year.

It's not as frequent, but you still got jokes on for Seth. I think I got, I remember getting two, though I'm told it was three or four. Shoemaker said it was more than two, but I remember, because I only remember the two, but he insisted it was more because he had remembered my name. Maybe he was thinking rehearsals or something, but I remember, I know I saw at least two air, and maybe I did get paid for three. I don't know what the third one was, but this was just for like half a season that I did it. And I didn't know that that was a big deal. Like I was kind of down on myself.

I was like, God, I can barely get anything on this show. And then they explained to me the odds, how slim it is back then when they're- Alex Bays, you're in trouble. You're going up against Alex Bays. And you're going up against, and you're going up against, and you're going going up against Seth. And so, and then at the same time, Malaney was there and Jost was there and Doug Ables. Megan Callahan was working her way up. So yeah, it was not a friendly, you know, Bay to try to swim around in. But I didn't know that. And that worked to my advantage because I was

just like, well, let's try this. Who knows? Yeah, I got a couple on there. And that was insane. And I, because with Jay, it was like, it felt like a family friend. I felt like I grew up knowing him sort of through these other, you know, this other family we knew. And with Seth, though, that was the first time that I really had that distant, oh, my God, someone else kind of thinks my writing is pretty good. You know, this person doesn't know me at all and has used a couple jokes. And it's Saturday Night Live, you know, like it's, it was awesome. So it was really cool. Tell me if I have this right and explain the logic because I do not understand.

you, on your own dime, you fly from, I guess it would be New Hampshire. You fly to Los Angeles and you go to NBC Burbank to take a meeting with Leno show to be a possible writer. But you know going in that they already hired the person. Why would you eat the money and go into a meeting? And sometimes they, do they just have these meetings for bureaucracy sake to say we interviewed enough, all these people? Is that well this is a crazy story so but i can remember it was all in one week that this all sort of happened uh it's funny when i think back on this now like my life changed for the the better in a one week span and it also uh you know went down the mountain in a one week span uh many years later so there's something as a bare naked ladies fan i guess i'm just haunted by one week um but

what happened was i had been faxing jokes in to jimmy and doing pretty well. I was doing about the same as I did with Leno, but I was getting a little bit more. I was getting like three or four a week. This is the infancy of late night at 1230. The beginning of Jimmy's 1230 show. And it was literally just because the tonight show with Leno had ended, Saturday Night Live is off for the summer. And I really didn't want to do it again. I felt like I had taken my best shot and it didn't work out. But I had heard that Jimmy was taking submissions from people. And so I just started doing the same thing. But then they let me email my stuff in. It was Wayne Federman. I just Googled Jimmy Fallon head monologue writer one night. And Wayne's website came up. His email was on there.

Send him an email. And the next morning at like nine, I have a whole bunch of emails. It's him saying, you know, John, welcome aboard. Yeah, I'm happy to have you. You know, so okay, great. And then there's the rules and here's the premises. I want to interject you were very smart to mention Jay's name. that you wrote for Leno because that gave you credibility with Wayne.

Yeah. Wayne loved Jay. So I didn't know this, but Wayne was a big Leno guy because Jay put Wayne on his show, gave him his first stand-up shot. So I'm getting about four jokes a week on Fallon. And to me, that felt a slightly better than Leno, but about the same. You know, like it was a little bit better money, but I didn't know that there were, I can tell you from working there for years.

There were people that struggled as staff writers to get four or five jokes on a week. They just couldn't find the voice of the show. So I'm the useful idiot who just doesn't know how he's doing well. So I get an email from Wayne on a Wednesday night. It was July 22nd of 2009. And he says, hey, we just want to let you know you're incredibly talented and we're really enjoying your jokes. And I'm like, that's kind of strange. Like, why?

That's great. It's the first time I was over the moon getting that email, but it felt like a heads up about something. And I was like, okay. So I have that in the back of my mind where he's like, we think you're incredibly talented. And I'm like, okay, that's great. So I still have this trip to L.A. coming up. And through back channels, I find out this is sort of just a meeting for to be polite.

And it's just so I won't bother Jay anymore because I had really harassed him. I had really called him for favors. What kind of favor? Just like if I needed a reference for anything. See, here's the thing. Jay made the mistake of saying to me, hey, call anytime you need something. In show business, in show business, call anytime you need something, means call me two times and that's it.

And if it works the first time, that's it. It's like your challenge in basketball. It's like you got it. It's over. But man, I kept calling him and to the point where he just didn't come to the phone. anymore. I blew that contact. I was immature and made a mistake. And whenever I needed a friend, like a friend from Emerson, she was writing a book about comedy writing and she wanted a quote from Jay. If I put her information down, said, hey, can you give Marty a call? He'd call her. If my sister,

if she was writing a term paper at BU and she needed to talk to Jay about communications, and I put her number, he'd call her. If I said, hey, Jay, I really want to come right for your show. And I put my number, eh, nothing. He wasn't calling back anymore. So, but they had given me this meeting. And so it was almost like a George Costanza thing where I knew there was no job. And they knew there was no, but we didn't know the other one news. And it was like a standoff. And I was like, well, I'm going to go out there, you know, and I'm somehow going to get this job. So on Saturday the 25th of July of 2009, I go with my sister and her now husband to see the Beach Boys, my favorite band of all time in Boston at the Hat Shell. There's, I think, 150,000 people at this concert.

It's just way out of hand, way overcrowded, but it's the Beach Boys, it's a free concert on a Saturday night. So you're, you know, bigger than the Fourth of July crowd at the Esplanade there with the Hat Shell and everything in Boston. So we're just trying to find a place to sit and this voice says, hey, you can sit next to us. And it's this pretty girl. And she's there, of course, with a guy. And I'm thinking, oh, of course, you know, there's this beautiful girl that I immediately feel drawn to. But she's scared there with this guy. And of course, he's got nice hair and all this stuff.

So then we get to talking and we figure out, I figure out that's her brother. She figures out that the girl I'm with is my sister. And then I say, well, hi, I'm John. Nice to meet. And she goes, well, I'm Rebecca. And that one day would go on to, she would go on to become my wife. and we would have a daughter together. But I was in love with her in that moment.

Like I knew I had, like, I was like, this is special. I've never really felt quite like this before. So by the time I went to L.A., I think it was Monday morning. So this was on Sunday, and that Monday morning I went to L.A., I'm going out there just to get them to blink. Like, I just want Jay to come in and go, I'm sorry. I'm so sorry, but I don't have a job, which is never going to happen. But I'm like, I want to, you know, I want to call his blood.

And, you know, I'm going to prove that I'm going to go out there. So I go out there and I have the meeting and it was, it was like, yeah, they admitted. Like, we were full with writers, but we're looking for like an associate producer who would work with the writers. And then if you work your way up, then you could work on the show and blah, blah, blah. And I end up having a great interview. It was with a woman. I don't remember her name. She was a producer on the show.

And I won her over by the end. It wasn't Debbie Vickers, though. It wasn't Debbie, but it was like, I forget her name. I want to say it was Linda or something like that. And I ended up really impressing her because I think I didn't care. So I'm driving after the meeting. I say goodbye to my friend. I'm staying with them, I'm driving the airport.

And she calls me back. And she says, hey, good news. That went great. And next week, Jack Cohen wants to meet you and Jay wants to come by and say hi. Can you stick around until next week? And I thought about Wayne's email and how that week since I'd been in L.A. I'd gotten two or three more jokes on Fallon. And I thought about Rebecca.

And I said no. And she went, I'm sorry? I said, no, I can't. I'm going back today. You know, give me a call. You know, I'd be happy to talk to anyone on the phone. And a week or so go by and Rebecca and I are going out and it's going pretty well. And they called me on a Monday night in August, finally, and said, we're going with somebody else.

And then the next day, I woke up on Tuesday to an email from the Fallon show saying, can you come down this week for an interview? This is Mike Shoemaker's assistant that reaches out to you. Erica Lancaster, who's now a big agent at CIA. And, but that's the crazy thing about this. The Leno, after years, the Leno window closed on a, a Monday night. And then on Tuesday morning, I get the email unrelated. They, no one's talking to each other. It's just unrelated coincidence saying, hey, can you come interview for the Fallon job? And so when I look at some of my immaturity throughout my career, some of my brashness and things like that that I feel bad for, I feel bad for it. But think about it. When you piss off Jay Leno and you tell Jay Leno no. And he basically tells you to take a walk. And the next morning, Jimmy Fallon says, come work for me. You know, you're going to have some unrealistic expectations that like, oh, well, goddamn, man,

things are always going to work out for me. I'm always going to figure it out, you know. So that summer of 2009 was a crazy, crazy time. It started out as such a empty, depressing state where I really didn't know what I was going to do. And by the end of 2009, it was one of the best years of my life, maybe the best year until my daughter was born. I want to talk about when you go to meet with Fallon and you meet with everybody. You've talked on podcast, you've done interviews where you've mentioned you can be a little socially awkward. I think we all can be, but you've talked about this a bunch of times. So you go in the meeting and for people that don't work in television or don't work in entertainment, when you go to a meeting like this, you're not supposed to, for the

most part, dress up fancy. Normally people that go to these, work at these places, dress down you know, some of them dressed sharp, but how do you, you go into the meeting dressed how? Okay. So, uh, I went into the meeting wearing, uh, very nice pressed khakis. Uh, I think I had socks with, uh, they were like navy socks with ducks on them, you know, like those old kind of like fancy gold toe socks, uh, boat shoes or even nicer loafers. Um, big baggy dress shirt, probably from when I was in high school, a blue, blue blazer, which was a little bit ill-fitting at that point. And one of my dad's neckties

from probably the mid to late 1990s. This is in 2009. And so I looked a little bit like a Chris Farley character. They were amused. They were very amused. To say the least, yeah, it was a, it's a story that I'm told is there's a lot of Reinman stories, as Jimmy has said. But that's a story that I'm told is still told to this day that when Ryanman wore his tuxedo. It wasn't. It wasn't a tuxedo. It was a shirt and tie and nice shoes and all that. But here's the thing behind that is that I met with Rick Ludwin one time via Jay. And I made the same mistake. I wore a suit, a dark suit with a tie and everything. And he and Nick Bernstein made fun of me and made jokes. And they said to me that in L.A., you don't have to do this just from now on. Like, just don't dress like this in L.A. And then maybe in New York, you do it, but you never do it out here. Just to interject, Rick Ludwin, Vice President of NBC Late Night, responsible for Seinfeld, a friend of Saturday Night Live, was really in Leno's corner.

He had an amazing career. I knew him, you knew him, just a really, really good guy. Please continue. And Nick Bernstein, we love Nick as well. Please continue. Yeah, I had a late night over at CBS and a friend. But it was, I went in there and thinking, well, it's New York. you know, I'm thinking madman.

I'm thinking, yeah, I wear a tie and you go in for an interview in New York by God. And I go in there and it was, I looked like a clown coming in. And they're all dressed, you know, I think the most dressed up person in the room is shoemaker because he was wearing a blazer. But I mean, you know, Jimmy's wearing a polo shirt and jeans and Miles is wearing like a sweater vest and, you know, maybe a maybe a tie because he was a headwriter. And Wayne's just wearing a, you know, a nice shirt and jeans and Chuck Taylor. sneakers and everything. So I go in there and I felt a little bit like, what's the name of that

the movie that there's that Halloween picture that goes viral, the woman that's dressed with the monster at a party for Halloween and she's the, the Bobbinank or something like that. There's some monster movie from Australia and it goes viral every year. She didn't get the memo. It wasn't a costume party. So she's dressed up as this like monster and everybody else is normal. That's how I was in the interview, the Babadook. That's what it was called. And I'm, that's who I was in that moment where I'm dressed up in a full, you know, how you doing? Nice to see you. I'm going to, I'm going to sell you some, some prescription drugs. And they're all like, what are you doing? But it was the icebreaker. And it set up who I was, I think, to them,

which is this guy's different. He's weird, as Miles would say, but funny in a way. And And at the end of the interview, it went great. It was like it felt like my life was being saved. Like I could not believe how nice they were and meeting these people just felt I was like, finally. You know, like just because with Jay, like I said, I burned things through. Like I burned out that contact. And he never really said like great jokes. You know, he'd thanked me by sending me money and giving me that credit.

But I never got really the pat on the back. back, you know what I mean? And when I went into the Fallon interview, there were a lot of pats on the back that I'd never gotten before. I could feel myself being discovered as a writer. Like I was like, this is, you don't usually feel it. You don't usually get to have that moment, but I got to have it. And at the end of the meeting, they just said, well, thanks for coming in. And God, I was like getting blue balled. I was just like, what? Like I was, I thought, like, man, I'm thinking my knees were weak and everything. I'm getting that thing that I'm about to get hired and it was like well thanks for coming in and i get up and i kind of turn around

and then i go back and i kind of hesitate i go i'm basically like a dog that doesn't know whether or not to leave the room and then uh miles is like you're right there man and i just go yes and then i set up a thing they still do it every now and then i guess in the ma i heard them do it once and then i hear they do it i hear from other people they'll do it sometimes but the thing with rindman the rhymingman impression is you always got to do like are we going to have the meeting at one or like there's an er at the end of the thing and that was established in that meeting where I said are you guys interviewing for an open position or and they go yeah that's that's why we head and I go are you going to call me

next week or like what's it going to be you really said that yeah I didn't yeah 100% that's great and now I'm feeling now I'm feeling it's slipping away it's charming though you charmed them. But I had just killed it in that interview, and I'm feeling it now. I'm like, now you're blowing it. Like, you just lost a no hitter. Now another guy hit a triple. Now here comes a three-run, home run.

You know, it was just like, oh, God. And Shoemaker says, he made some joke about my tie. Now, earlier in the meeting, Jimmy had said, he knew my hometown. He said, he knew Northampton because he just did a show there. And I knew he'd have been in North Hampton Mass. And I said, I think you mean North Hampton Mass. And there was a silence. and I said, I always like to correct the person I'm trying to work for in the interview.

And so when Shoemaker's like, yes, there is a position here. He goes, we didn't fly you down in New York just to compliment you on your tie. And then at the exact same time, Jimmy and I go, which was purchased in North Hampton. And we look at each other. And he came over and gave me a hug. Like he didn't just, he gave me, shook my hand and pulled me in for a hug. And that night at 721, I got the call from Wayne that I got the gig. And I was told that it was like, you had that prop of the crazy outfit and you had the presence of mind to save yourself with Jimmy.

And you had that nice callback joke at the end. And I think they had two interviews after me. But it was funny. It was the same thing where they were like, we're going with Ryndman. Like they already knew they were going with me. And I think they had the other people in as a formality. But it was, yeah, it was that thing. And when I saw Rick at the show, because he was still there for a year or two,

he would come by even years later. He's kind of like an emeritus executive. And I'd always say, man, you know, you tell me about that suit thing and how you guys got a kick out of that. That was a little bit in the back of my head when I was getting ready for New York. I was like, you know, if you go in and you're dressed funny, use this to your advantage somehow. So, yeah, that's how it worked out. I have to ask you about this. So this is on a Friday, it's the hundred.

tape in, is that correct? It's September 8th, 2009. Boy, you do your, Mark, you do do you do you know stuff, you know stuff better than I do. It was a hundred. It was, I know you do. It was the, it was the hundredth episode. A little bit of some more context, too, is that I think that morning, Jimmy had to shoot a scene for 30 Rock and he had to be there at like 6am or something. And then I, someone, I don't know if it was Jeselnick or Bronson or somebody told me that he, I think He'd forgotten about it. So Jimmy had a Jimmy Fallon Thursday. And then, oh, the car's at my place at 5 a.m. on Friday.

Yeah, I was walking in. There was someone there would say there was a bit of a headwind that day. And it was tough. It was tough getting to, because at first he was a tough, tough egg to crack. But like I said, just being goofy, I think he just felt bad for me in a way. But I think it, but I think it worked in my advantage because he was like, this poor guy he's like we have they even said they're like we have to hire him like what's going to happen to this guy he's like a puppy on a highway you know i have to ask you this though

because i did i listened to a bunch and read a bunch of interviews um with you and tell me if i have this right though you kind of worked them to use a wrestling term because i know you worked for the wwe you knew that rick and nick got a kick out of you dressing up so did you purposely do that to go into felon knowing that they might they might get a kick out of it or not i i did it so i think in the back of my head i was i sort of had that in the back of my mind which was i'm going to look presentable to them and if the if nothing else i mean i thought shoemaker would wear in a tie i thought gabin might be wearing a tie miles was wearing a tie i don't where the hell does he get off making fun of me all these years god damn he was wearing one too but it was a little bit of a work

in that when they acted like, you're not supposed to dress like this. I kind of already knew that in the back of my head. But at the same time, I'm a bad dresser. I'm a really, like I've gotten better at it now. As you can see,

I dress like a grown up. But at least at that point, I was a New Hampshire kind of trashy dresser. And I didn't have that sort of in the middle. I didn't have cool shoes that I could wear that would go with. I mean, I had T-shirts. I had Hawaiian shirts.

That's it. I mean, that's like Lauren back in the day. Yeah, but I was, but I was literally, I literally dressed like Jimmy Buffett all the time. And you can't dress like that necessarily going into that kind of interview. And I knew that I was the deer in headlights anyway. So I was like, dress the part. And what made it especially ridiculous, though, it was about 96 degrees that day. So they're all dressed like, they had a party and everything after work.

So like, you know, Jimmy and Wayne and everyone else now, they're all dressed to have fun. And then comes this guy looking like Hanigan, the salesman from Conan. I look like a Brian Stack character. But I just, that's how I am as a person, where it's like I struggle with the in-between game, so to speak, where, you know, either I'm dressing like garbage and Morgan Murphy and Eric Legend and Justin Shains are making fun of me because I wear an Oscar in the Grouch shirt to work every other week. Or I put on the jacket and tie, you know, and it was just like, I think another thing about it, though, was. it was it's the dream it was the dream show that i always wanted to work for i always wanted to work for the 1230 late night NBC show uh it's new york city it's 30 Rockefeller plaza it's just a gorgeous sunny day and i was like let's just go balls to the wall like let's just let's just give everything

we can to this interview so that if it doesn't work out at least i'll always have it in my mind that i dressed nice and i acted polite and uh half of that happened acting pretty awkward but You're 26 years old. Are you the youngest writer at that point? Mike DeSenzo was younger than me. He had been there since the beginning, and he's a few months younger. His birthday is in the summer, I believe. But other than that, we were the youngest.

I mean, everyone else there was at least, I think, three or four years older than me. And you're in an office with Anthony Jeslnick. You're sharing an office with him. Yeah. Yeah, it was me, Wayne Federman, Jeremy Bronson, and Anthony Jezzelnick when I first got there. and then Wayne was there through Thanksgiving, and then they transitioned to when he left. I think he moved back to L.A. Bronson became the new head model of writer. But yeah, I was with Anthony for almost a year, I think, in there. So, yeah. What was that like to be 26? And you don't

really have any other experience, knowing, working in person at a late night show, hired on staff that you're just getting so many jokes on right away. I mean, sometimes it takes a while or somebody maybe in the beginning gets a lot and then just plateaus. It is a grind, but you are, I mean, your bad and average is extremely high from the get-go and you maintain that. Look, I mean, the first year at Fallon, especially like when everyone, the whole group was there.

People, Jezzanick left, then people started to leave. Tim McAuleth left. Then I think Blyden was gone, and then Morgan was gone at some point. It changed. But, dude, it's funny. I never until just recently, you know, my wife and I, we got divorced, but have since reconciled and are now really good friends and hang out together. And we've started, you know, it's, we're co-parenting and it's, it's positive.

And as she says, one step at a time. And, you know, you never know. but so we started talking a little bit more and she's helped me remember a lot of stuff that I'd forgotten over the years. And that first year at Fallon, I'd forgotten how magical it was. It really was just unbelievably great. Um, you know, from the apartment I got, which I absolutely loved and just, you know, it was in a story of it. It was, it was great. It was just renovated. It was, uh, it was on 41st street between 31st Avenue and Broadway. Oh, nice. I know that section. lived near there. I'm, I still live in Astoria. Oh, yeah. I can feel the vibes, man. And I, no, I loved it. I loved Astoria and neighbors and everything. It was cool. And it was just fit me. And there's a lot of standups that I met living in a neighborhood to work where I loved everybody. And it was just, um, the first person that came over to shake my hand on my first day was Jezelnik. And I had heard that I'd be sharing an office with him. And I'm not going to lie, I lost sleep. I was really scared. I was really skisling.

scared because I'd had another job where I'd had an office mate who was like Jezzlenick's character in real life. And that had been very difficult on me. So I was like, here we go again. And he gets up from his chair. And he comes over and gives me the biggest handshake says, you know, are you John Rydenman? Yeah, he goes, welcome to late night. I'm Anthony Jesselnik. You know, like right away. And I'm like, oh, man. And then he's just so nice. He took such care of me. Shoemaker took care of me. Uh, Jeremy Bronson taught me how to, to be a professional. It was just great, but you're right in that my first full week there working for the show, I got 15 jokes on that week. If you get five on, that's a good thing a week.

If you get 10, that's like what you're expected. If you get eight to, you know, if you're new and you get like eight, that's really good if you're new. I got 15. And there was jokes that got cut for time. So I would have had closer to 20, you know, but there was stuff that got cut from rehearsal because we, because, you know, sometimes you bounce your own joke out. You have two jokes about the same story, but they say something different. Okay, which way are we going to go with this? Jimmy, you know, I feel this way about, okay, lose it. And, but here's, here's what it did. It established another one of those crazy rules where now I had stay up late writing the night before. So you get half your jokes written. And you got to get at least 15 jokes per week. You have to. That's crazy. Like 15. is, that's three jokes a day at a show where you're competing with Jeremy Bronson, Morgan Murphy, and Anthony Jesselnik. And then Eric Legend would come along soon after. So, I mean, those four people I just mentioned are, I hate to get dark here, but Anthony would appreciate it. So hi, Anthony. But they're in memoriam people. They're going to be on the

in memoriam someday. You know what I mean? Like, they'll be in the Hall of Fame. That's the Hall of Fame for writers. Unfortunately, you get it when you're dead. But I mean, Legend's got St. Dennis Medical coming out. So he's going to be big time. And he's done all the sitcom writing. Jeremy's done everything under the sun as a sitcom writer. And he's had his own shows on TV like the mayor, Jezzelnick's Jezzelnick, Morgan's Morgan.

And she also ran mine her family. And Wayne Federman is the one reading the jokes. And at 26, you say, I have to get 15 jokes on every week against these people. And if I don't, it's a failure. And if I fail, I have a choice. I can either be really down on myself, which really creates an aura. People feel that you're negative or you're angry or anxious or whatever.

Or I can lash out at the person who's picking the jokes because they cost me my 15 jokes that week. And now it's Friday night and Rebecca's there and she wants to be boyfriend, girlfriend, but I can't be happy at all because I only got 13 jokes that week. God damn it. And if only Jeremy had put a couple more in mine in, you know, I would have done better, you know. So it was a magical time, but it set expectations really, really high. And I think that looking back, I wish that, I wish two things. I wish that I'd either gotten off to a little bit of slower start.

So I kind of ease my way in and appreciate it more. Or, you know, there are a lot of times that 80 miles could have really smacked me down a little bit and could have really said, you either stop, you know, being like this and you either kind of drop your personal expectations, you'd be more of a team player or else we're going to part ways. Or maybe you've actually could have done it. You know, maybe he could have said, go away for two weeks and learn your lesson, come back. But, you know, yeah, at 26, to do that well right out of the gate, to have your second cycle option picked up the third week you're working there. I mean, my third week there, I knew I was going to be there for at least six months.

That doesn't happen very often. And I also want to mention, is it your recollection that Anthony Jeslinak wasn't getting anything on? Bullsh. I'm sorry. Like, you caught me. That's what he says. I'm just repeating what he said. Like, I'm getting my, I'm finishing my master's and about to start some other TV work. So you got me on a day, Mark, where I'm full of coffee. And I'm going to say things I regret. So God damn, it's great for your podcast, but I don't know about me. No, I mean, I've always tapped as around. Anthony did fine. He, I mean, at the end, he didn't get anything on because he was writing Jeslnick jokes just to kind of, you know, he knew he was leaving. And he knew that everyone loved him and he could get away with it. And it was

funny. But I remember Anthony getting like four jokes a show, like, you know, for a while. I remember him getting Anthony was until he got anxious and rambunctious and knew he was going to be famous. Rightfully so. And he did the right thing. He got out. He didn't stay there like me and so many other people and bitch and get, you know, jaded and unpleasant to be with. He left when he knew he was starting to get that way. And God bless. So many of us should have done the same thing. But he could, he as a person is one of the nicest human beings I've ever met. He's one of the most supportive people to comics and to writers. And he was like, almost in a way, like, I'm going to get quoted somewhere for this and he's going to get pissed and that's fine.

But he felt like the anchor of the monologue team sometimes. Like, he really felt like the backbone because you could count on him to write that good, heavy, smart joke when we really needed it. Sounds like Pet McCormick on Carson. Yeah. It's funny. It's like, I would say they're here, Arthur Meyer over on the sketch side where people that you could, you could count on to do the job and, like, lead by example. And, uh, Anthony was, he was great. And I learned a lot from him, but another one of the rules is that his thing was, I remember him saying like, I can't even, I can't even sleep until I write 15 fucking great jokes the night before.

And I was like, just 15 jokes. he's like, no, great jokes. Not just jokes. That'd be fucking great. Whatever I need to write to get to 15 great jokes. I can't even sleep because what if I oversleep the next day? And he went on this thing and everything. So now I had write half your jokes the night before get 15 jokes a week. And also make sure 15 of those jokes you write the night before are quote unquote, excellent, fantastic, you know? I read an interview with you that you were, you were going to bed around 2 a.m. Is that around then? Writing, you were up writing. And until 2 a.m. I would, I think on the late night show, when I first got there, I wasn't that

bad. I would usually go to sleep, I think before our show even came on. So I would be asleep by like 1215. I might stay up a little bit later. You know, this is when Conan was doing the tonight show. And I was curious, you know, I was rooting for Conan. I think we all were. Yeah. I was rooting for Jay too, but I was rooting for Conan in that I saw the writing on the wall. I knew that we were going to get pushed a little bit too early if Conan got bounced. And I had friends that worked for Conan more so than people who worked for Leno and things were tense between me and the Leno people at that point because of the way I'd been that summer and the way they kind of had me in when they didn't really have a job at the time. So I would watch Conan, and especially if I had a

friend that was doing stand-up or whatever. And then I'd usually go to bed. And I would try to get there around 8 or 8.30. And usually Jeremy Bronson and I'd be the first two in there. And I like that time because I really love Bronson. And I really looked up to him and learned a lot about taking that job seriously and embracing it from him. And he wrote similar jokes to me. So we pushed each other. You know, there was a friendly rivalry there. You know, I grew up a basketball fan. We've all seen those speeches of Larry Bird, Magic Johnson saying, you know, I knew when I was a kid, I was out there shooting. There was somebody else that was doing an extra half hour. So I'd stay out an extra half hour. And I remember when I met Jeremy, I was like, he's the guy for me. Like,

every time I was faxing in jokes at 2.30 instead of 2. So I spent an extra half hour. He was that guy that put in the extra time and really tried to do the best he could. But we figured out that I wrote better stuff late at night. And so it just started to creep later and later. And so it was usually about 1 a.m. until about 2016 or 2017. And then when Miles started to get phased out and as Trump was president, that's when it began to become 2.2.30, you know, whatever. And the flip side was, I wasn't able to.

sleep in. So I was, you know, but in the early years of late night when it was the boring wonderful days of Obama, where all you cared about was just what goofy thing Biden did that day and how big Kim Kardashian's butt was, you could kind of write your jokes a night before. And so I'd write them and I'd sleep in. I'd roll into work around 10 or whatever, and it was great. And, you know, but it's risky. You can't bring your work home like that, though. Like, that's what I say to people now where I'm like, get up early, you know, especially if you're, if you have a wife or a girlfriend that's living with you, don't bring that home, you know, like it's, you know, because it gets you in trouble, like when you write jokes about Trump and you don't really think much of it. And then the next

thing you know, he's running for president, allegedly because of it. So, you know, I want to talk about your book. You wrote a book in June, The Garden is always greener and praise from Gary Goldman, Wayne Federman, who we talked about. I know that you're a big Celtics fan, and you got to work with Larry Bird at Fallon, which I'm sure was a huge thrill of yours. Yeah. Garden's always greener.

Got a copy right here. Yeah. The premise of this book was much of it was written during the writer's strike when people, you know, and I didn't really know what I was doing in my life anyway, strike or no strike. But it goes back to a pandemic project where when we were all locked down, I had NBA 2K and I had a PlayStation 5.

I got like the last one from the store near me because I just had a hunch we were going to be inside for a while. I am a big Celtics fan. I got to produce that bit with Larry Bird when he was on the show that time. And I just love them. And I noticed on the game, there were so many people modding it at the time, meaning modifying it and creating different scenarios and stuff. You could go back in time and play forward from like a different era,

like a different season. So you can go get the roster from like 1980. and the draft classes and everything from there. And so I said, I wonder what would happen if Len Bias had lived and played for the Celtics. Now, Len Bias was this great player that the Celtics drafted second overall in 1986. He's going to be Michael Jordan's rival. They're going to just keep on winning forever because they had Larry Bird and Kevin McHale and Robert Parrish at the time. Len Bias, two days after he's drafted, overdoses from cocaine.

And it's a very tragic thing. It's a fluke thing and they break it down and they realize he had a laced shipment or whatever you want to call it and died very tragically doing something that a lot of people were doing at that time because of that millennials like me never really had that guy as the Celtics. You know, we had Paul Pierce. We were older by that. You know, he was more like almost a Gen Z kind of dude. So the book is a comedic look if a character based on Len Bias had come along and played for the Celtics starting. in 1986 and how it would have changed allegedly pop culture. So I ran the simulation.

I played a couple of games. I recorded everything in a Google Doc that happened. And there was a lot of funny stuff. There was a lot of like, you know, oh man, imagine if Dennis Rodman had played for so-and-so a team or imagine if Shaq did get drafted by whatever. And it was really funny. And then when it was all done, I wrote a story around it that's like a fake sports Almanac. So it's like you're reading a fake sports history from the NBA from like 86 on.

But other stuff happens too. Like Tupac gets saved. OJ. gets stopped before he can do anything. You know, Seinfeld has a different act or different arc. And it's sort of just a redo of the 90s sort of tongue in cheek that has a lot of late night to it. Like it's got monologue jokes to open parts of each chapter. There's a couple of mock top 10 lists in there as if someone had gone on Letterman and done that. There's a cheer scene, a perfect strangers scene, home improvement scene. It's a dude read, and it's just a fun thing. And it's written in memory of my dad who passed away from Alzheimer's because it's been revealed how reading can really help you and keep your brain sharp, especially if it's fiction. And there's not enough men reading fiction

right now. This has a ton of callbacks in it, a ton of running gags, a lot of jokes. Um, and funny NBA, like cartoon versions of Bill Walton and Michael Jordan and Dennis Rodman and Shaq and, you know, all that stuff. And, uh, it's, you know, it's, it's, it's basketball fan fiction, basically. But people who've read it so far, I've liked it. I know it's been, I guess it's gone around the writer's room at a family guy I heard, which is really, really cool. And I've heard from a lot of those guys that I'm friends with now. I didn't know them until I did this book saying, how much they like it and, you know, they're showing their Celtics friends and stuff. So, yeah, for the holidays, it's out there.

It's gardens greenerbook.com. It's on sale, I believe, at Amazon right now, too, with a discount. And I'm donating from the proceeds I get to the Alzheimer's Association in memory of my dad. So it's a really fun book. That's fantastic. My friend Dan Pastornak, who's a comedy, big comedy guy, he kind of makes fun of me because I always say this on the podcast, but it's, It's true. I have several pages of notes left to ask you, would you come back on the podcast

to do another episode? I just want to mention, it's fair to say that there was, there was a lot of drama when you left Fallon. I mean, there was, I mean, you've been very open. I, you know, I hear the stories from people. I've worked in TV. I know a lot, but you've been publicly open on a bunch of these. You did stand up, actually, on both late night and the Tonight Show with Jimmy Fallon. There's so much more to talk about. I want to talk about the correspondence dinner as well. Yeah, that would be great. I would really like that. And we, yeah, we need to do that. Yeah, I'd love to, Mark. Yeah, that'd be fantastic. Thank you so much for having me. This is great. 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-nighter.com forward slash podcasts. Have a wonderful week and I'll see you next Tuesday. I'm going to be the I'm going to be. And I'm I'm I'm

I'm my and the I'm I'm going to be able to be. I'm going to be. I don't know.

Thank you.