Talking Comedy with Jason Zinoman of the New York Times (Part 1)
Chappelle, Letterman, Seinfeld and the Roast Of Tom Brady
Jason Zinoman is one my favorite follows. Jason is critic at large for the Culture section of The New York Times and writes a column about comedy. As I said in the audio version of this interview, his work is “not stupid. There's a lot of stupid in comedy, and I don't feel like (he does) takes.”
We spoke for around an hour, which you can listen to here.
As for the below, it’s what I call Transcript-ish. I have run the audio through Descript which provides a pretty good transcript. I then ran it through Claude AI and asked it to clean up the work. For example, whereas Descript had it as below:
Although that makes it sound, sometimes it comes very easily as I'm sure. And sometimes. More work doesn't always mean better work is one thing I've learned.
Whereas Claude has cleaned that to
Although that makes it sound, sometimes it comes very easily as I'm sure. And sometimes more work doesn't always mean better work is one thing I've learned.
Then from there I gave it a QUICK once-over while I sit under the umbrella poolside on a very hot Saturday afternoon. I also took out some parts that make sense for audio but not for written word. That’s what I mean by Transcript-ish. I’m a one man band trying to get it all done.
Here’s part one with Jason:
JOHN: … I'm curious about your approach as someone who just does off the top of his head, 10 minute podcast and maybe a half-ass written substack. I know how long it takes me to do that. So to appreciate what you're doing for the New York Times. Also you gotta be putting in a ton of work.
JASON: … yeah, it's a lot of work. Although that makes it sound, sometimes it comes very easily as I'm sure. And sometimes more work doesn't always mean better work is one thing I've learned. And that's one thing that's evolved over the course of this.
JASON: For instance, I would say when I started this job, I spent a huge amount of time going out to see shows, clubs, and I still do that, but I don't do it as much as I used to. And that has to do both with how comedy's changed. But also I think that I try to spend a little bit of time every week thinking about letting my mind roam and thinking of ideas. And then if I have a good idea, I try to find the right form for it. Sometimes that's a review. Sometimes it's an essay. Sometimes it's a bigger piece and there's a profile. And it's funny sometimes like the things that I write in an hour or a half hour are the most popular and the things that I sweat over, like I'm working on something now for months. And no one cares.
JOHN: I feel like I totally know that one.
JASON: Yes. Yes. And there, sometimes they're wrong, but they're not always wrong. So sometimes you cannot trust your... Let's put it this way as a critic, I'm first a critic and I'm a big believer in something. I'm a big believer that your first impression isn't always right, but it's always important. So you have to be really sensitive to your first impression of something. And it's why people like Pauline Kael, who's probably the critic who most inspired me as a kid. She would write, she'd go see a movie and go home, write the review right away. And because she really valued that first impression.
JOHN: I'm happy to hear that you're not clubbing as much as you used to. One of my guilt trips I ran SiriusXM comedy for 10 years, 10 years ago now. But even then it was hard to go see shows because I was still expected to be in the office and be a manager from 8am until 5pm. Six, call it. So to stay out to one 30 in the morning doing shows was difficult. I tended to rely on the people who were younger on my staff and then to keep my knowledge fresh, I'd hit festivals. And as I always tell this audience, if you go to a festival, don't go see Chris Rock. You can go see Chris Rock some other time, go hit all those smaller shows. That's where the action is. I'm upset that Montreal is gone or perhaps back or this new group that bought it, but no Montreal this summer is a bummer.
JASON: It's interesting to hear what you do, because I think that's a very smart strategy. It's... I have taken the opposite approach which isn't necessarily better, which is that if anything, I undercover festivals because I feel like a lot of the people you see at festivals, I already see New York, but what that means is like comedians from other cities, when they come through here, I make a point of trying to see them, or I try to go to LA periodically to see that, but I miss things for sure.
JASON: And there's no question that you could, it's funny. I, the truth is that there's like a pool of performers in New York. And if you go often enough, you see them all. It's changing, but it doesn't change radically. It doesn't change like the number of people changed. I still like to go and I think I pick up things. I learned things from going, but now the thing is you could probably, the most time efficient way is probably just to look at your computer and file it. Cause everyone's online and there's so much material online and a lot of consumers of comedy are first accessing comedy, not from clubs, but from a clip on a TikTok or Instagram. So that has to change. I feel like if the way that we have to evolve along with the consumers.
JOHN: Yeah. And I, for any content creator, no matter the format, we're all living in a headline world, right? So the easiest thing to write is why Joe Rogan, Shane Gillis, and Nikki Glaser are something that'll get the clicks as opposed to, "Hey guys, Gianmarco Soresi is awesome." Just, it doesn't do the same.
JASON: But Soresi will contact you and be like, how come you're not writing about me?
JOHN: He's fantastic. Switching gears, I wanted one of the main things I wanted to talk to you about Dave Chappelle. It bothers me that he has seemingly chosen to turn his legacy into... The second line in his obit is going to be something about the trans community. And he's so much better than what he's done on the last few specials, which is, Jason, you know why I had you on today? Because of the trans. And he slaps his knee and he mugs for the camera and he gets a laugh. And he's so much better than that. And I don't know why he's dug in on that. I'd be curious to your thoughts.
JASON: It's a good question. Look, I love Dave Chappelle. I wrote an ebook on Dave Chappelle, eight years ago, searching for Dave Chappelle. I grew up in Washington, DC where he's from. I have, I'm around, he's a few years older than me, but I've been following his career since the eighties. I have a tremendous, he's incredible comedian, his sketch show. I think it... People have now forgotten about it, but it's one of the greatest comedies ever on television. And he's one of the greatest, he's one of the greatest stand ups. I think it... His first special is terrific, and he still has a lot, I say all this as a way to be like, it's one of the, I'm agreeing with you, and one of the reasons it's depressing is that when we talk about Dave Chappelle, we tend to talk about these culture war things. And because that's what he's put out, put forth. And so why has he chosen to do that? I think Jerrod Carmichael made us ask a similar question recently. I, my sense, if I, again, I'm just speculating, is that Chappelle always liked to, didn't, you know, prized his freedom. Prizes independence.
JASON: And I think he, I think the good faith, genuine interpretation is that when he did trans jokes and people got offended or said, don't do it. His first instinct is to then double down, right? And that's always been his first instinct. It's been his first instinct through his whole career. I could, I can, we can go chapter and verse even before he was famous. I've written about, before his Chappelle show, he had a big falling out on his comedy on a ABC show called buddies. I've traced this, in this impulse has served him. In this case. Look, it may have served him well for his audience. He's still selling out. He's still popular, but for his art, I agree with you. I think it's kept him in a rut. And I'm still optimistic when I see a new Dave Chappelle thing and I hope he moves past it. But yeah, the, what's interesting to me, the last one came out. Is that I don't even think it caused that much controversy. I think people were just bored.
JOHN: Yeah, I imagine in your travels you've run into him. He'll do sets and I'm being generous with that. He'll take stage time. And he's not even really working out. He's just talking to the audience when he does that downbeat soft spoken Dave, and he'll just come out with some brilliant things just to listen to that may be and or even funny. And he's got that there. And I just, I'd like to just see him do something else. But to your point, Dave Chappelle announces new Netflix special already. The conversation's going to be, is he going to bring this up again? And it's, I think you nailed it. It's boring.
JASON: It's predictable. I mean, if you were to say like, what's the least interesting thing for him to do next? It would be to talk about that again. I that's the part of it, which is flabbergasting or I think that the other issue might be is that he always had these two modes, which was doing like a standup set with this, with more traditional collection of jokes and his very idiosyncratic style. And what you described this, like he would go into, he would go into club and he would be on stage for four hours. And there was something incredible about those sets. He could go places that others could not. And I believe he got... he fell in love with that and there's something indulgent about those. And I think that's true for not just in terms of the amount of time he's spending there, but also they became very self serious. This bothers me less than other people, but I think another reason people got bored with them is that he seemed his material seemed less punchline driven. It seemed less about being funny and more about being profound. And if he's saying things that are profound and poetic, that's fine. And maybe it's better than fine. It's great. Thank you. But if he's saying the same thing over and over again, that's a problem.
JOHN: All right, new premise, off all the recent protests that Jerry Seinfeld ran into, I find myself wondering, what if Jerry went political? Now I know that's crazy, he's 70 years old and it's very easy to just write it out and go, hey, did you ever notice? But, what if Jerry showed off and went all in. Could you ever imagine that in a million years?
JASON: No, but I mean I would be interested. I think there's another question which is similar, which is what if he went vulnerable or introspective personal. And I think there's room for that. I think that he, I don't think, I think people would be interested in either him going political. I don't think he wants to, and I don't think he has to. I don't even think he's going to come, from the last interview I saw from him, he doesn't seem like he wanted to come out with any special ever again, and he wouldn't need to. He wouldn't need to see. And, people forget, but he came up at a time when everyone didn't need to release specials and he didn't. He, for most of his career, he didn't release specials. And he could, and he did just, he did obviously did just fine. Some people think that he has gotten more political. But I'm with you. I don't think he, I don't think he has.
JOHN: I thought I found all the backlash to the Pop Tarts movie bizarre. I liked it. I thought it was, this is a silly movie. We're having fun. My friends are in it. Want to turn your brain off for 90 minutes and people seemed like mad that movie even exists.
JASON: It was weird. I know you mean I think some people were mad about the interviews in which he said things like you know the PC left and the were ruining sitcoms or whatever. But yeah there was the initial response from some I think one film critic called the worst movie of the decade or the year. And I was like that made no sense to me. That made zero. How you could that there's something going on outside of the screen to think that a movie with that ambition and also that amount of, that there's plenty of talent on screen there is the worst movie and it's not like I say ambition. Low ambition. It's not a movie that's swinging for the fences.
JOHN: Yeah, it's not like he made some bro dude version of Oppenheimer and missed the politics of it. It's a Pop Tarts movie.
JASON: Yes, it's a Pop Tart movie. It's, it was a, it's a bizarre response, but I, that's the age we're living in, right? That I think the more hyper, hyperbole, you, you mentioned if you put Joe Rogan in the title, it gets a lot of hits. The other way to get it is to have a more extreme point of view, right?
JOHN: The roast of Tom Brady, I feel like it cut through, seems to have done well. Did Nikki Glaser step up in class? Did Tony Hinchcliffe step up in class? Are these now names that the civilians would know? Actually, let me sidebar there. This comes up a lot. There are a lot of really popular comedians. But if you and I walk down the street and grab 100 people in New York City and said, hey, Andrew Schultz, what are we going three for a hundred?
JASON: I think you're right. I think you're right. Yeah, no you're putting your finger on a big phenomenon of the moment, which is like what does it mean to be a famous comedian in 2024? Andrew Schultz played Madison Square Garden, right? And, there was a time when that was like, hardly anybody, hardly nobody had played Madison Square Garden, but he's played Madison Square Garden. And as you said, I think most people don't know who he is. But that, I think that's not just a question of comedy. That's a question of the culture in general, which is that it's so fragmented. It's so balkanized that you, as long as you have very passionate fans in your niche, you can sell a lot and be very successful even without being widely known.
JASON: I think it's also answers the previous question, which is that why is everyone so worried about Jerry Seinfeld? All the people who became famous in that generation have a kind of fame that's way bigger than the kind of fame you get now, with the exception of Taylor Swift. If you manage to get famous, even Rogan, I think, is an example of this. Where Rogan likes to act like he's anti establishment, anti mainstream media, but I have this sort of pet theory that the difference between his fame and, Tim Dillon, Andrew Schultz, who will never be as famous as Joe Rogan, is that Joe I apologize for the misunderstanding. I'll continue cleaning up the transcript as before. Here's the next section:
JASON: Rogan was on Fear Factor. And Joe Rogan was on News Radio and he hosted a, after Bob Costas left later, he, or he had an NBC talk show for a second, though, that's a bigger fame than these podcasts fames that you get now. It's a kind of fame that reaches people, a much broader demographic than you reach now.
JOHN: I must have erased from my brain. There was a Joe Rogan late night show.
JASON: I did a piece a year ago. It's now, it seems already very, maybe longer than that. It seems very dated when Daily Show was doing rotating guest hosts. And I was making an argument for how this might not be a terrible idea to do permanently. This is before they announced Jon Stewart, which is a better idea, but or once a week. But although I guess they still do, I guess they are doing rotating guest hosts around with Jon Stewart and I was looking around for precedent. And I realized that in the late nineties, NBC did this after, I may be getting some of the details wrong, but it's in my story. After, you know, Letterman and they had a crazy series of people who like hosted for a week, then a week, and among those people were Joe Rogan. And he had, he interviewed, and I'm like, I don't know, gay people, he interviewed. It was a similar version to his podcast, but it was on NBC. And I was really shocked. It's, I couldn't find any versions of it online, but I nailed it down that, that had happened. I found it on old, like TV guide lists, those things.
JOHN: Oh, wow. You're going to send me down a rabbit hole and I didn't forget I will circle back to my Nikki Glaser question, but now I'm like three questions deep. I just had Mark Malkoff on and he re-triggered my late night obsession and I spent the week watching YouTube videos and somebody made this homebrew thing about the Carson Letterman Tom Snyder trifecta and I was, I just, I'm back into that whole move and I know you wrote a Letterman book. Can you explain to me why I worship 12:30 Letterman? Lasted a year and a half at 11:30 Letterman after spending a decade going, man, if only I didn't have to stay up to 1:30 in the morning, if only Dave were on at 11:30, I would watch Dave every night and then a year and a half into it. I don't know if it was just, I was in my mid twenties and going out and doing things people do and not watching late night TV. But 12:30 Letterman is my North star 11:30 Letterman. Okay. And then he'll put out something on Netflix and it takes me three weeks to watch it. I, what is wrong with me?
JASON: It's so funny that you asked me this question today because you and I are identical on this point, and just today somebody sent me a podcast. In which it was the guy who does the Letterman podcast Mike Chisholm. And he said, "Oh, I mentioned you on a podcast" and he was on a podcast with somebody else. Sorry to be on a podcast talking about another podcast, but my name came up and it was asking, I guess the podcast host was, said, did you press him when he was on your podcast about why he focuses so much on his late night, 12:30 show and not on his CBS show? And there was a kind of... there was a, they were upset both of them because they both really they're, they're, they both like the CBS show. And it made me wonder for a second, because I... putting aside me for a second, I think to people who are younger, who maybe didn't grow up with that show, the CBS show means more, but I've watched both as a, as an adult. So my opinions on them are not just like nostalgic.
And despite what they said in this podcast, the reason I didn't is because I agree with you that from 1982 to '93, David Letterman on NBC made some of the most brilliant talk show comedy and the most innovative talk show comedy ever that really created a sensibility invented all kinds of forms mainstream to sort of irony. That is really significant. That deserves that will be to your point about legacy. That will be the lion's share of his legacy.
BTW My guest on the podcast today IS Mike Chisolm, of you want to check that out. I will share that transcript in a few weeks.
JASON: Now, his first couple of years in the CBS show are probably arguably the more popular. And were more covered more because of the late night wars. And some of them were quite good and there were periods in the CBS show that were better or worse, but in my opinion, the NBC show was vastly more ambitious and better than the CBS show. Now that again, there are big exceptions, certainly his response to 9/11 and many other ones. He still was David Letterman. You still was doing great work. But and my book is essentially a book length answer to the question of why, right? If you want to know why that is buy my book, Letterman, Last Giant of Late Night and part of it has to do with him. Part of it has to do with the network, but a lot of it has to do with what's around him and the writers around him and the relationship between the writers and Letterman and all that. I would say that you were just smart and discriminating, and that's, that's why.
JOHN: I think what attracted me to it was the whole 12:30 vibe, and once Conan found his fastball, he had this same vibe of, maybe this bit isn't working, but, I know it, you know it, we all know it. Let's just stick to it and laugh together with it. And then you go to 11:30, which is a different animal and you have to wear an Armani suit and you have to wear shoes. And it just was more, I've always called it establishment Letterman as opposed to the 12:30 like, uh, we're off our game tonight. We got 47 minutes left. Whatever.
JASON: Yep. Yep. Yep. No, I think it was clearly, a bigger, more show, busy show in a big theater where the previous show was intimate and. It felt like conspiratorial between the viewer and Dave and it was going backstage and doing all these fourth wall breaking things. It was very different. There was a, it was a very, I would make the argument that it was, the things that really made him unique. The new version of CBS was going directly against that doesn't mean that he was totally different. He still had some of that irreverence. And I think what's interesting, you bring up what he's doing now. It's remarkable if you would have told me, the young version of me who loved his late night show that Letterman would be now doing a show in which he interviews famous people and is incredibly complimentary and gushing about all of them. And solicitous. What made him really stand out as an interviewer in the 80s, and you could just go and look at the press on this is he adopted a kind of almost hostile, if not skeptical attitude towards, the celebrities who came out of promoted uh, and that was part of his appeal. So it's interesting. He's, I don't blame him. That's, you know, you, but, but it's quite a 180.
JOHN: The next rabbit hole I want to go down is trying to track down clips of his daytime show until I watched that homebrew doc this week. I had no idea that Petricks or viewer mail were leftovers from the daytime show. I've barely seen clips of that.
JASON: It's incredible. It's incredible.
JOHN: Are they out there?
JASON: There are. Yeah. Yeah. Yeah. If you go on YouTube. There's, they're not all of them, but a huge number of them. And, he and Meryl Marko all, a lot of the great stuff from the late night, if not most of it, were established in the morning show. And, they had, Andy Kaufman has maybe his most, one of the most brilliant appearances ever. Was on the morning show. There's incredible Steve Martin appearance. They did. I'm pretty sure they definitely just do with Patrick's first in the morning show. I think they might've done viewer mail. A lot of the man on the street stuff with Hal Gurney, the director started with him on the morning show started there, it was the wrong time slot, but they were trying things there that it was the blueprint was established there. And just when they figured it out, they got canceled. And I think that, that's what was the secret sauce to the show is that by the time that they started on Late Night they had a much better sense of what they wanted to do than they would have if they did a morning show.
What I learned today is there’s a limit to how long a transcript can be. So if you’d like to listen to the entire interview, you can do that now. If you prefer reading, I will share Part 2 next Saturday!