Mike Sacks is a good bad writer

By Brian Braiker

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You could say Mike Sacks knows a little about comedy writing. You could say “he wrote the book on comedy writing.” It would be a cliche to say that, of course. Bad writing. Possibly just the sort of bad writing that is almost good enough to be comedy in and itself — in the right context.

This is not that context. But it is the context in which Mike Sacks joins us on “Brooklyn Magazine: The Podcast” this week. An editor at Vanity Fair, a contributor to the New Yorker, among others, and the author of 10 books, Sacks is both of student and practitioner of the art of humor writing. Two of his books are collections of in depth interviews with profoundly influential comedy writers from the legendary — think Mel Brooks, James L. Brooks, Terry Jones — to the less known but no less important — like Peg Lynch, Irv Brecher, Jim Downey.

His other books take a little more explaining. In 2017 he wrote and self-published “Stinker Lets Loose!,” a deliberately badly written novelization of a 1970’s trucker movie that never actually existed. He’s also written a novelizations of a non-existent John Hughes-type movie called “Passable in Pink” and one set in grunge-era Seattle called “Slouchers.” You sort of either get the joke and join him for the ride or you don’t.

Sacks also co-wrote “Welcome to Woodmont College,” a fake catalogue from a really expensive and really shit boutique college, which Vulture named one of its top humor books of 2022.

Sacks has a big week ahead of him: “Stinker,” which was turned into a star-studded audio book by Audible, will be republished by Simon and Schuster January 10. Also being republished this week is Sacks’ “Randy! The Full and Complete Unedited Biography and Memoir of the Amazing Life and Times of Randy S.” The premise of that book is that it’s an unpublished memoir Sacks found at a yard sale written by an average Maryland dirtbag who’s come into some money.

Lost? Stick around. Sacks joins us to discuss his career, growing up on the “honky” side Maryland, trucker movies, his love of bad writing, his punk-ish approach to humor and what he’s learned from interviewing some of the best to ever do it. 

Sorry, Mike, but this interview has been edited for concision and clarity. Reader, you can listen to it in its entirety in the player above or wherever you get your podcasts.

Your book, “Stinker Lets Loose!” is being re-released this week by Simon and Schuster. Tell the story behind the book. It’s a brilliant premise. It’s a novelization of a non-existent ’70s trucker movie. How did that come about?
It came about that I was going through a very bad time personally, and I was sort of frustrated with where I was in a professional sense. I’m contributing to Vanity Fair and New Yorker or other magazines, but it wasn’t as fun as it used to be. It was sort of tethered to the current day, all these articles, so they sort of went bad. They weren’t evergreen. And I just really wasn’t having fun at it. So I thought, “I’m going to do something that I don’t think is going to bring in any money. I don’t really think anyone is going to read this,” but I’ve always been fascinated by novelizations. I grew up with novelizations, pre-internet, pre-cable. They were really the only way to relive movies.

Quentin Tarantino, I think is the most recent example of a novelization of a film that I saw. They did “Once Upon a Time in Hollywood” as a novel. I don’t know if you saw that.
I loved it, but he copied my idea, the bastard.

Totally. So what was the idea?
So the idea was that I love novelizations and I grew up reading them. So I thought it’d be fun. I love that style too. I mean, I like bad writing and it’s not easy to put out a novelization, because it’s sort of cheesy. It was done by professional writers who made a living at this. I have a collection of them and I was going through and reading them. In some ways they interest me more than it would a serious short story in say the New Yorker, that type of writing. It’s just very American, it’s very pop culture, it’s kitschy. And I thought it would be a good Trojan horse to get some satirical ideas across and also do a parody of these movies that I grew up with in the late ’70s, trucking and CB movies, which you really don’t hear about. I mean, unless you grew up in that era, you really don’t know about it.

I showed it to my daughter recently, “Smokey and The Bandit,” and she might as well have been looking at something made on the moon. I mean it was totally foreign to her. It was totally bizarre, almost fantastical. But if you grew up during that time with Burt Reynolds and all those other, Dom DeLuise, all these bizarre people.

The great Jerry Reed.
Jerry Reed is an underrated performer and artist, country music artist. So I thought it’d be a fun thing to do, both from my standpoint to write it and also to make fun of something that I hadn’t seen made fun of. So I thought, screw it, I’ll do it. I’ll put it out myself and just see what happens. And I wrote it in about six months. It was fun to write, put it out there, self-published it. My then girlfriend, now wife, designed the cover. She hand painted it. She’s a designer at Random House, Danielle Deschenes, and I put it out and two weeks later someone got in touch with me and said, “Can I have the audio rights to this?” So I said, “Sure, take ‘em.” I’m not thinking anything twice about it. And two weeks after that he called and said Jon Hamm was attached to play Stinker. And then Rhea Seehorn was attached to play his wife, Phillip Baker Hall, Andy Richter, Paul F. Tompkins, all these great people involved. So that came out of this novelization.

You mentioned the cover. I love the cover. It’s an incredible, it looks like the real deal movie poster from a 40, 50-year-old Burt Reynolds movie with an angry chimp and a truck and a cowboy with a mustache. The whole nine. It’s great. So you grew up into these CB movies. I remember those movies.
I grew up in Virginia, Maryland, and New Orleans. So they were big where I grew up and they would play at drive-ins. I mean they were huge. I remember seeing “Hooper” at a drive-in and long lines outside of theater to see Smokey and the Bandit 2 and 3 not just 1. So I always just assumed the entire world knew about these, but a lot of people don’t because-

We were all watching “Star Wars.”
Well, exactly. I mean, I prefer these movies, the “Star Wars” people think I’m insane, but I will watch “Smokey and the Bandit 3” over “Empire Strikes Back” any day.

Why is that?
Well, there’s looseness to it. It’s very punk. It almost looks like they don’t know they’re being filmed. There are chimps in every one of these movies. I love chimps, especially when they give the finger or the raspberry to a sheriff. There’s always outtakes at the end. That was way ahead of its time. It was very loose, and I always felt like I was part of this fun gang that just happened to get together and shoot this movie. And from a comedic standpoint, I thought Burt Reynolds was and is one of the best comedic actors. Just so natural. He really didn’t give a shit. I just love them and they remind me of that time, a very specific time in which America’s pop culture was very Southern. Jimmy Carter was in the presidency. Country music was huge. Truckers were the current cowboys, modern day cowboys. Was post-Watergate. Very anti-government.

“Dukes of Hazzard.”
“Dukes of Hazzard.” That’s right, exactly. And it was funny because it really ruled for a few years and then it totally went different instead of Southern rural pop culture became Northern urban with rap and break-dancing and that sort of thing.

So you’re just sitting at home writing. You said you were going through a bad period. You’re like, “I’m going to write a novel based on a book that doesn’t exist and I’m going to make the writing intentionally bad.” It’s bad in a way that’s so specific that it’s almost like, do you care if the audience gets it or do you want the right audience to get it?
Well, it’s a good point because I love shit writing and I love to parody shit writing, but it has to be written in such a way that is good shit writing. I have read various pieces live. I opened for David Sedaris a few times where I’ve read something that was purposely poorly written and the audience some got it, and if you get it, you get it, and a lot didn’t. A lot of people are perplexed by such a thing, but there’s something about authentic shit that really hits home for me. I mean something that’s not meant to be shit, but it’s just shit, bad writing I love. I think it’s very American, and a lot can be done with it because when you write as a bad author, you’re sort of playing a character role like he would in a movie.

Within each of these books I always look at it as a certain type of author in this case from the ’70s, living in a one-bedroom apartment outside Los Angeles who always had dreams of making the movies, but has to now make a living writing novelizations to grade-D movies. But you mentioned the look of it. That was important for me too. It had to be authentic. There’s even fake crinkles in the cover that Danielle put into it, and there’s a fake ad in the back for stereo equipment and also a list of other novelizations you can supposedly buy. So I wanted it to look like something where if you stumbled across this book, you would genuinely think that it was a used book from the late 1970s.

You’ve done a series of these satirical, or almost parodies, I don’t know if you call them satire parody or both. You did a “Pretty in Pink” one, or a John Hughes one, called “Passable in Pink.” You’ve done “Slouchers,” which is the ’90s Seattle grunge era. You’re setting it up as a found text. Same thing with what you did with “Randy.” What is it about keeping you at arm’s length from the writing itself? Is it, as you say, to play a character? Or it gives you leeway to be deliberately bad? All of the above? Or does it inoculate you, Mike Sacks? “I didn’t write this.”
That’s part of it. I mean, the margin of error is definitely built in. So if someone says, “I don’t like it,” it’s like, yeah, of course you don’t like it. It’s supposed to be a piece of crap. But as far as comedy, I always liked things that were authentic, whether it was Andy Kaufman going on stage and pretending to do this with no wink to the audience. I don’t really like books that has a big sign across the cover that says “satire” or “parody.” I just like being a little confused. I mean, I don’t think there’s anything wrong with that. I don’t think readers are used to that. And I’ve been told we shouldn’t confuse readers. And you know what, they’re right.

I didn’t get into it to confuse anyone. I just think there’s something very interesting and maybe a little more effective if something looks to be exactly like something I am satirizing. But also by doing this, it can be a parody of these movies like you mentioned John Hughes or the early ’90s, Gen X movies. But you can also satirize various aspects of it. I mean how America has changed since the ’70s, ’80s, and ’90s. How people used to look at various elements of what’s happening in the country, whether it was a total disregard for having African-American actors in movies or how they treated Asian actors or just the way we treated women.

You walk that line very finely in “Stinker” and “Passable in Pink.” You make jokes that are right on the edge. But the joke is about how the material that you were riffing on was racist or at least ignorant of race.
Totally.

Both in and “Stinker” and in “Passable in Pink.” And it’s a risky line to walk, but I think you’ve threaded the needle well. [For example, with] “The Chonger” character as Long Duk Dong.
I was nervous about that. I wrote that character because my best friend growing up was Taiwanese American and we went to see ’Sixteen Candles” in the theater together. And I remember his face walking out when people were talking about Long Duk Dong, and he was upset and rightly so. And he said to me at that time, and I never forgot it that, there are no Asian characters that he can really associate with on screen. I never really forgot that. And going back and looking at these movies again with my daughter, and she pointed us out too. I mean, it’s just all white. Some of these jokes, whether it’s the rape jokes in ‘Sixteen Candles” or Long Duk Dong.

They’ve not aged well.
No, they haven’t aged well. Now as far as satirizing that you can often be confused with what you’re satirizing with you yourself as a writer. And I was worried about that with Audible. I had an amazing audio cast for “Passable in Pink.” Adam Scott, Gillian Jacobs, Rhea Seehorn, Bob Odenkirk, Judd Nelson, Laraine Newman. And they kind of buried it because there was that character, “The Chonger,” that I wrote, who was played by an Asian American actor, comedian. But I think they misinterpreted the satire. And with the new book, the re-release of “Stinker Lets Loose!” there are a few lines in there about how the Asian characters were treated in these movies. And typically they were just stereotypical Chinese. Not even Chinese American, but Chinese tourists taking a lot of photos. That was the joke back then.

So I said to my editor, “Is this too much? Should we take it out?” This going to be through Random House and my editor’s Asian American. He said, “No, I want you to leave that in there. I’m insisting you leave that in there. Because when I look back at those movies, that’s all I see are these stereotypical depictions of Asians. And I think it’s a good way to approach it.” Now there will be people who I think might confuse what I’m trying to satirize with me as an author and confuse the two.

That’s the risk you take.
Yeah, and I think you have to be pretty straightforward these days. You have to say, I am satirizing this, but it’s not really done in these books. I hope people do get it.

You mentioned the Audible thing, which I mean, it’s an incredible cast. You’re re-releasing the book, “Stinker Let’s Loose!” Do you update the text at all with this new publication? Do you change any jokes that you didn’t like or whatever?
I went through the whole thing. There were a few things added to Stinker that was read live at Sketchfest in San Francisco a few years back with Jon Hamm and Kevin Pollak and Andy Richter, Paul Tompkins and Busy Philips. They did well, but there were some lines that didn’t get laughs so I took those out and rewrote some other things. Now with Randy, more was rewritten. It became more of a story and I filled it out plot wise. So there’s more chapters in the Randy version that’s coming out.

For the listeners, Randy’s one of those books where the premise is you found it at a garage sale and no one really knew what it was. And it was this guy who hired some out of work freelancer to write his own biography. He got inheritance from his grandmother and he’s just this real Maryland dirtbag. You like these characters that are not people you’d want to hang out with. How do you approach a character? It’s his story as narrated to this writer and you were like, I just found this, I didn’t write it and presenting it “as is,” quote, unquote.
It was like a Medici would in 15th century Italy, paying some artists to make themselves look good on canvas or in prints.

Samuel Johnson’s Boswell, or whatever. What is it about this character, this not very likable guy that you really went all in?
I like the guy. I mean, first of all, this was what I hung out with growing up. I mean, I worked retail for 10 years, 15 to 25 in Maryland, in Virginia. And I met a lot of people who were like this Randy character and I was friendly with them. I also played softball with people like this. Where they’re very provincial, they vacation at the local hotel that’s next to a fake lake. They have very few creative outlets, they’re very content with their lives to go to sports bars on a Friday and Saturday night and watch the Capitals or the Nationals or the Orioles. I just had fun with them. I mean, I genuinely like them, but there’s also a frustration that I saw from their standpoint with a lot of my friends that how does one make it? They didn’t know anyone. They didn’t know anyone who knew anyone.

So if they had these creative dreams, whether it to write music or to write books or put out films, it was just very tough for them. They didn’t have and in. And their parents didn’t go to college and they didn’t have connections. So that always interested me, this frustration that I saw on their part on being creative and making a legacy and lasting while also being opposite of most artists where they’re totally content and happy with their lives where they had fun and they did fun things. So this Randy character is sort of an extenuation of that where he is I guess a dirtbag. But I think hopefully he’s strangely likable. I mean, he’s a lonely guy and all he wants to do is reach out and make connections and he just has no idea how to do it.

So you talked about growing up in Maryland. How did you get out? What’s your story? I guess you got into journalism first. What was it like growing up there in Maryland among a bunch of Randys?
There was two different types in Maryland when I grew up, I call it “the wonky and the honky.” So you have the wonky, which was Capitol Hill, lobbyists with bow ties with red, white and blue suspenders, lawyers, lobbyists, that sort of thing. And then on the other hand, you have the real D.C., which can be very blue collar and can be somewhat Southern, can be somewhat honky. And they are either working blue collar jobs or retail jobs. And I always leaned more towards that side, because I had no interest in the wonky being a politician or a lobbyist or a lawyer. So for 10 years I worked retail for basically minimum wage in the outskirts of Maryland in one case behind a housing project. And I worked with people who were older than I was and they were stuck working these jobs where you had to wear chukka boots and you had to wear a name tag and you had to stand up when you ate lunch from the Chinese restaurant down the strip mall. It was a dead end.

And my fear was I would remain in that world and I very easily could have. I was there for too long, I worked too long. But there was something to be said for that too in that I met a lot of interesting people I wouldn’t have otherwise. And a lot of these characters, including Randy, are characters that I could have very well been. I mean, I could very easily still be in Maryland in Gaithersburg or Poolesville in a one-bedroom apartment driving off to a temp job or to a retail job every morning. But just through luck, there’s certain things that happened at certain times. I got out of that world and got into writing and editing in D.C. and then lucked into a Washington Post job. I was temping at Washington Post and I snuck into the job office, which you’re not supposed to do.

I just happened to know this ancient word processing program called XWrite, which is pre Microsoft Word. And it was only because of that, only because the Washington Post was so behind the times that I ended up getting this job where I helped to edit the syndicated writers like Jane Bryant Quinn and Tom Shales and George Will and Ellen Goodman and all those people. So it was just a matter of making things happen. But it was also luck as there always is in certain cases. But really my mind, my heart is still back there. I’ve lived in New York for 20 years now and I really don’t know much about it, but I still feel that that world I grew up in, in Maryland, Virginia, I know very, very well, even though it’s changed a lot, there’s become much more cosmopolitan. But I know it well. I just know those people well. That’s what interests me to write about.

It’s funny, my first journalism job was at the Post, which I got through temping in the marketing department, which was a total joke. But you entered at I guess a higher level, sounds like. How do you go from retail to editing Jane Bryant Quinn to ultimately, now you’re writing for the New Yorker, you’re writing for Vanity Fair? How does that progression go from D.C. to New York?
Not well. I was not good at the Washington Post and I was miserable at the Washington Post. It wasn’t what I wanted to do. I wanted to write comedy. But in D.C. at that time, this was the late ’90s early 2000s, it was very dry when it came to comedy. It’s much better now. I mean, Patton Oswalt has come out of there and Dave Chappelle. But when I was there, the only thing that was there comedy wise was pretty much the Capitol Steps, which is a political song, charity group. Mark Russell.

Terrible. Dave Barry was one of those syndicated columnists [at the Post].
Well exactly, yeah. Tony Kornheiser, all those guys. And I hated that sort of thing. And it was very much Kennedy Center comedy. It was not punk comedy that you can just go to and here’s something that I would enjoy. So it was really very lonely and there was no comedy and was when I got up to New York that I started meeting people. But then in D.C. when I first started writing for McSweeney’s and other online sites, I just seemed like I was free-floating in space. It just seemed like no one else was doing it. I knew no one else doing it, and it seemed very solitary. Now it seems like every other person I meet is a comedy writer. That’s totally different than it was when I was first starting out.

Do you think that’s because of the democratization of media and everyone with a Twitter account or a TikTok thinks they can get a TV Show if they’re funny?
Yeah, and I think it’s brought in a lot of fresh talent that you wouldn’t have seen otherwise. I think it’s great and it’s never been a better time to be a comedy writer because you have the ability [to] put out your own books, put out your own podcast, put out your own movies, basically, put out your own audio. And that just did not exist when I was coming up. It just felt very, very lonely. But the segue from my retail background and my temping background in DC it was not easy because I was working with people who had journalistic degrees. I did not have one. Who seemed to have connections, who seemed to know where they wanted to go. Even to this day, I feel like a bit of an outsider where I just put my head down and do what I do. But I never came up in a group or within a system that helped me at all. I just feel like it’s very solitary. It’s me against the world, in some ways.

That resonates. I mean, when I was at the Post, it was very lonely for me for the same reason. I remember someone who wrote a — it was interesting; it wasn’t a brilliant piece of writing — but it was a nice feature story in the Sunday Magazine. And I told her, I’d love to do stuff like this. And it was not rocket science. And she’s like, “You have to work for years before you can write a feature like this.” And I’m like, “Give me a fucking break. It’s not that great.”
Well, that’s the thing, there were very few outlets and people were very protective of it. So I never felt like I was worthy of doing and I didn’t know how to do it. In the end, you figure out how to do it. But when people would try to stop me, which happened all the time, I guess that’s why I’m so hardheaded now. I don’t like when people block the gates and I will try to come in from the back. But that’s all I came up against. “You can’t write for New Yorker, you didn’t go to Harvard, or you didn’t go to Iowa Writer’s School.” Which is true, I didn’t, but I don’t really think you need to in the end.

I think there’s fewer obstacles now, but that sort of thing is very D.C. I had to leave D.C. to accomplish what I wanted to accomplish because you’re exactly right, especially the Washington Post, when it was the only game in town, they really took themselves seriously. And unless you had been doing it for years, even if you were capable of doing it, it was not allowed.

I definitely noticed that. And that’s also why I ultimately left the Post, because it was too gatekeepery. But now you’re established, you were saying you’re editing at Vanity Fair, you’re contributing to the New Yorker, you’ve got bylines all over the place from GQ to New York Times. And yet you sound like you were dissatisfied. By any accounts as either freelance or full-time editor, you sort of made it. What was so dispiriting about having achieved that?
So I had been freelancing for years and there was an issue in my personal life and I was just also burned out by writing things I didn’t want to write for magazines and things I didn’t necessarily find that funny or interesting. Things that were connected to the current day that wouldn’t look good if you came back to read it in the future. So I’ve interviewed quite a few comedy writers and across the board there seems to be this feeling that only when you do what you want to do, how you want to do it, will you achieve some sort of happiness. The reason why you got into comedy writing to begin with was to put out what you wanted rather than writing say lists for Esquire or pieces about Trump or what have you.

That was a good lesson. And I mean you see it in very famous comedians, whether it’s George Carlin or Richard Pryor, where they say, “This isn’t working for me, this current role because it’s not who I am and I have to become what I become, whether it works, whether it becomes successful or not.” And then at that point, their careers really explode. And I’ve heard that too from comedy writers where you really have to do what you want to do, how you want to do it. So I thought, “Screw it, I don’t want to write these little listicles, I don’t want to write pieces for this magazine or for that magazine that doesn’t interest me. I want to do something a little different. Whether people get it or not, I don’t know, but it’ll interest me.” Actually the original idea was a novelization to the Zapruder film, but that didn’t work.

[Laughs]
I tried that. It was a little too dark, if you can imagine that. But it’s just something I wanted to do. And I said, “Screw it. I’m home. I separated. I was drinking a bit. And I’m just like, if I’m going to do it, now’s the time.” It really worked out how people said it did. Because when you put something out there, I could have been pitching this idea for 30 years to my agents and publishers and audio producers and they never would’ve accepted it. Oftentimes you just have to produce something and show them what you have in mind and show them something tangible so they can understand it. And I think by doing that, other avenues will open up, other opportunities will open up and good things will happen. I’m very much into the put it out yourself, DIY punk aspect.

When I grew up in D.C., to me, the only creative hero I had in the area was Ian MacKaye of Fugazi and Minor Threat. Local guy who put out his own records, which was just unheard of in the D.C. area. Put him out the way he wanted to. He owned the rights, sold them for $10, had $5 ticket shows for all age audiences, and he created the career he wanted for himself. And that was a huge lesson for me.

Well, it’s interesting because you’ve been able to maintain this duality where you are working for Condé Nast, but you’re also sort of doing the punk rock self-publishing thing. I want to ask about those interviews that you were alluding to. You’ve gotten two books of collections of your interviews, “And Here’s the Kicker: Conversations with 21 Top Humor Writers and “Poking at a Dead Frog.” I love these interviews. You’re talking to truly legendary figures in comedy, some of them household names, some of them right under the radar, Bruce Vilanch, Mel Brooks, Roz Chast to name some of the more better known ones. Did you use your access to get to these people as a fanboy, for advice, to network or just because you thought they’d yield genuinely interesting interviews or all of the above?
I had never interviewed before, but I got into it selfishly where I grew up a huge fan of comedy. And I would look for books of interviews with comedy writers or even just about comedy. And there’s none or very few. It’s either about “SNL” or “Your Show of Shows” or syndicated sitcoms like “M*A*S*H.” But there was nothing on “Mr. Show” or on “Letterman” or all these shows I love. So I always wanted to put together a compilation of interviews. And I love interviews because it’s not me telling the audience about these people, they’re telling the audience directly. I’m just asking the questions. I don’t want to be a part of it necessarily.

You said to me the first time we met, you said that you don’t like interviewing.
I don’t like interviewing.

Which surprised me because these interviews, they’re very good. You’re good at it. You know your material and you’re good at asking questions that yield interesting answers. I haven’t heard that in every interview necessarily. So you have a knack for it.
Well, thanks. The reason I don’t really like it is because they’re a tremendous amount of work, I mean for each interview it’s up to 50 hours of research and it’s a pet peeve of mine, a very specific pet peeve. When I read or watch or listen to an interview with a comedy writer or comedian or comedic actor where the host tries to out-funny the interview subject. And I see that all the time and I always want to remain in the background. I could ask funny things, I could say funny things I guess, but it’s not my show. It’s like having a guest over to your house. It’s their show. And I wanted to do sort of a Dick Cavett way where he was capable of being funny, but he was genuinely interested in his guest. And it’s such a rare trait. Trevor Noah was terrific at this, but a lot of comedy interviewers, it’s about them. And it was a pet peeve.

So I wanted to produce a book that I would’ve wanted to have read growing up, wanting to get into comedy writing and knowing nothing about it. The person I was writing for in this imaginary world was a girl or a boy in high school who was skipping math class to go to the library who wanted to get into comedy writing. And stumbles upon this book, with people who have made it and can tell and give advice on what one should do and what one should not do if they want to get into comedy writing. I mean, for me growing up it was very mysterious. How the hell does one become a comedy writer, I had no idea. So that’s really what I wanted to do. And from a selfish standpoint, I wanted personally to know what I should do and not from these people who have made it. Who are very successful, especially those who were aging and who might not be around long. So I interviewed quite a few people who ended up passing away after I interviewed them for the book.

For the first book you interviewed Irv Brecher who wrote for Groucho Marx, which is incredible. So it’s interesting you said you wanted something that provided some sort of advice or roadmap or whatever for aspiring writers or for yourself. But the advice that they give when you explicitly ask for advice in these interviews, there’s nothing that is especially revelatory or prescriptive. You learn more from their own personal journeys. Each journey to having made it is different. What is a through line?
That’s right. There’s nothing to teach. When people teach comedy, it’s usually taught by people who can’t make a living at comedy and a through line through all these people that I interviewed, there was some overlapping advice from all of them. And basically it’s, “Listen, I can’t tell you how to be funnier, but I can tell you what worked for me.” And it usually is: write what you want to write. Don’t get into it for the money. There’s going to be highs, there’s going to be lows, but you have to keep pushing forward. And one form of comedy writing is no more or less important than the next. If you want to write for the stage, it’s no less important than writing for the New Yorker, which is no less important than writing for sitcoms, which is no less important than writing a graphic novel.

And you shouldn’t feel any lesser if you don’t want to do something that you think you have to do. Also, it doesn’t matter who you are, you can be from anywhere. You don’t have to go to the Harvard Lampoon. A lot of these early comedy writers, you mentioned Irv Brecher, who wrote for the Marx Brothers. He literally grew up on the streets of New York and had to support his family by comedy writing. And that’s a hunger that you don’t really see anymore. This was not a Harvard Lampooner who through connections made it into that world. That interested me because quite a few of those people that I interviewed, whether it was Mel Brooks or Larry Gelbart who wrote “Tootsie” and created “Mash” and wrote “A Funny Thing that Happened on the Way to the Forum,” they were very streetwise.

They had a lot of life experience. A lot of them were in World War II. And that’s another thing that I learned: that experience matters. It doesn’t necessarily matter if you’ve seen every episode of “The Simpsons” and know every joke. What matters is if you know character and have stories and meet people of different backgrounds and just live a life. So that was another overlapping piece of advice that I learned. One woman I interviewed, her name was Peg Lynch. She basically invented the modern sitcom. She wrote for radio in her teens, and she was 96 when I interviewed her. And she was very street smart, very wise. And all her comedy came from just living a life. It wasn’t through attending comedy courses. Fascinating character.

These are not nepo babies.
Oh my God, no. I mean, in fact, her mom was a nurse at the Mayo Clinic in Minnesota outside where they grew up. And as a teenager, a 13, 14, 15-year-old girl, Peg Lynch would interview celebrities coming through the Mayo Clinic where her mom worked. And the first person that she interviewed, unfortunately there’s no tape available of this, but imagine that she’s 14, 15 years old. She asks Lou Gehrig, who is there being diagnosed with ALS, if he will give her an interview, a local interview for the radio, and being the guy he is, having just been diagnosed. He says, “Yes.” So this woman, this girl at 14, 15, her first interview is with Lou Gehrig, which I just found amazing. So this is what one has to do. And then also advice about what not to do. And there’s a ton of things that I wish I hadn’t done when I just started.

Who surprised you the most? Who were you just bowled over by how either candid they were or helpful?
I would say David Sedaris I was a huge fan of. I had seen him perform a number of times. I wrote him a letter. He didn’t have email and I wrote him a letter to his agent and I would say four or five months later, he got back to me and he was incredibly sweet. I was in New York City, he was in Paris and we ended up on the phone for six hours, and to the point where things were going so well. That’s what I kind of learned too, a lot of these people who were really successful are really decent people. And that comes through in their comedy. They’re not in it to get back at people. They’re not in it for the wrong reasons. They’re in it just because they’re decent people. Quite a few people I interviewed were not decent people and they didn’t make the book. But the ones who are really successful, like David or Larry Gelbart, just total mensches and no ego and just were in it for the craft and are willing to talk about it for hours.

Who is the least-mensch who didn’t make the cut?
A lot of people didn’t because of lack of ego, I think. You need a bit of an ego to talk about yourself and some were shy. So I had no problem with that. They didn’t make that, that’s fine. And it was my fault I asked the wrong questions or this and that. It was only one person who was a disaster, who was mean. And I had to end the call early. And this is after me doing like 40 to 50 hours of research. I can only mention this now because she just passed away. Her name was Anne Beatts. She was an early National Lampoon writer. She was the girlfriend of Michael O’Donoghue, the famous writer for National Lampoon and “SNL.” And she became one of the first writers for “SNL.” She’s famous for writing one of the most infamous fake ads in National Lampoon magazine history, which was the Chappaquiddick Volkswagen.

Basically the joke was their Volkswagens float. So if Ted Kennedy was driving a Volkswagen the night that he was driving his date back and they fell off a bridge, they both would’ve survived. So that was the ad for Volkswagen. But it’s a very strange interview. I don’t know if she had a chip on her shoulder. I don’t know if she was protecting something. I don’t know if her boyfriend, Michael O’Donoghue was the real writer for some of these things I was asking about. But I ended it after 10 minutes because she was just so mean and so unnecessarily mean. I’ve never done it since and I’ve never done it after or before. I just said, “This isn’t working. Thank you so much. Goodbye.” And that was it.

Oh wow.
It lasted about 10 to 15 minutes.

I’ve had awkward interviews, I’ve had interviews with mean people, but none that I’ve pulled the plug on, just suffered through it.
It’s funny, this woman, she was portrayed in “30 Rock” by Carrie Fisher. I don’t know if you’ve seen those episodes where Carrie Fisher comes back as the legendary veteran comedy writer for the show that they’re working on and she’s such a disaster that they just can’t work with her. So if you go back and watch those reruns, that’s her.

What did you learn about the differences between comedy writers who are just writers and writers who are also performers? Is there a difference?
A lot of people say these are interviews with comedians and they’re not, these are comedy writers, but quite a few do have experience. Whether there’s David Sedaris reading in front of thousands or of course Mel Brooks. And what I did learn, which was very helpful to me, is that as a writer, even if you don’t want to be a performer, there’s a lot to learn by becoming a performer. You learn a lot about writing if you perform, especially improv. Improv is incredibly valuable for a comedy writer, even if you don’t want to perform. And that’s really because you get an immediate reaction, which you don’t get if you write to the page, you see what works and what doesn’t work and you see it immediately. And I think a lot of times comedy writers for the page feel they have more time to entertain than they might.

And when you get up on stage — I was told I still don’t have the balls to do it, improv — that you learn very quickly that there’s not much time and you have to get to it and you have to get to it quickly. And they told me that that affected their writing where they cut out the fat that went straight to the meat and it was only because they had to entertain in front of people without a net and which is an incredibly frightening thing. I’ve read in front of people, but I’ve never done improv. I wish I had the balls to do it.

Let’s take an improv class, I’m down.
Would you do that? That’d be interesting.

Sure. Yeah, I would. Are there any sort of coups in here in terms of gets? Like you had “Simpsons” writer, John Swartzwelder gave you his first major interview. What are you proud of having gotten in some of these interviews?
Well, he’s not in the book. He was for New Yorker. I was proud of that in the sense that I had asked him years ago for the first book, which came out in 2009, if he was interested. And I wrote to his PO box number, he didn’t have an email. And he was very, very sweet, he wrote back and said, “No, I don’t want to do it. And here’s why, and thank you,” which is fine. I don’t mind people saying no. I once asked John Waters if he’d be interviewed, and he called me and said, “Listen, I can’t do it. Here’s why.” And I just respected that. What I don’t like is when people never get back. There are certain people I still haven’t heard from. I asked him, John Swartzwelder again for the second book, and he said, “No.” And then just out of the blue, I thought, “Oh, I’ll ask him again.”

And I was writing for New Yorker this time, and it was because I was writing for New Yorker. He grew up reading it, all the humor, and he wanted to talk about his books as much as or more than “The Simpsons,” which is fine. His books are absolutely brilliant. And it was because of the New Yorker name that he said, “Yes,” much more so than who I was. So I was happy to get him. Very interesting guy. I think a shy guy in a lot of ways. A lot of interesting stories about he owns the world’s oldest baseball.

Whoa!
Isn’t that crazy? He rents out Dodgers stadium, just a shag flies with his friends, which is just a dream to me. It’s interesting because to interview someone who’s never been interviewed is very difficult because you don’t know what to ask or not to ask. At the same time, it’s very difficult to interview someone who’s been overly interviewed too much. Like, I’m about to interview Elton John for New Yorker. And that’s really tough because when you ask someone who’s been asked everything, how do you not bore them?

What are you going to ask him?
I’m going to ask him more about a looking back and how he feels about his career and you want to ask him questions about “Your Song” or “Benny and the Jets” and “Goodbye Yellow Brick Road.” And the audience wants to hear about it, I want to hear about it, but you also don’t want to bore the guy. So there are different ways, I guess, about going about it. Asking about how production was done on his albums, which I find fascinating. The drums on his albums sound better than any other albums I’ve ever heard, by Nigel Olsson. So I mean just very specific things. And they’re heavily, heavily researched and heavily, heavily written. This will not be an improvised interview. And that’s what makes this so difficult, is it’s a bit of pressure and each of these questions are written out to the fullest. And it’s not like talking to a friend. It wouldn’t be like me talking to you at Double Windsor. I mean it’s very, very concentrated and very prepared for.

What you see on the page. How boiled down is that from what you walk away from the interview with?
Quite a bit. It’d be like anything, even like a “60 Minutes” interview, there are hours that they don’t show. They narrow it down to what’s interesting. Nothing has been changed word wise, but a lot has been deleted. And it’s not a trial transcript, it’s not a CNN transcript. It is meant to be entertaining. And if certain questions don’t work from my standpoint or from his standpoint, then they’re cut. Or if I ramble or if he rambles, it’s not necessary. It’s cut. So it’s very concentrated. Look at a conversation, it’s not something that would be something you would overhear at a bar. It’s much, much more dense and focused.

The one knock on “Dead Frog” in all of the reviews that I’ve read was a lack of diversity. It’s overwhelmingly male. There’s a handful of female writers and it’s all white. I’m giving you the opportunity to respond to that knock.
Okay, well first of all, it’s not all white. Larry Wilmore is in there. The knock really hurt me. Just because someone isn’t in there does not mean they were not asked. If you were to name someone you would want in there a female or say an Asian American writer or this and that, I can guarantee you they were asked many times and either they didn’t get back to me or they said, “No.”

Now, one of the things that I noticed starting that book, this was 2015 I think I started it, is this is when podcasting and sites that were geared towards interviews with comedy writers really came out strong. And I think there was a lot of competition for certain writers, whether they’re female or African American or Asian American, that they ended up saying, “No,” to various people. But I can guarantee you that if there’s a writer you’re thinking of who wasn’t in there who might have been a woman or Asian American or African American, I guarantee you they were asked and said, “No.” I mean I can’t force people to say yes to this thing. It is time consuming. It’ll be hours, sometimes weeks through email. This is not a short email. This is a Playboy-length, Paris Review-length email. It takes a lot of time.

These are conducted over email, not in person?
Well, no. I mean it can be over phone, now on Zoom, or email or a combination thereof. I mean, I ask a lot of follow-up questions and I do like to point out before we start, this is not going to be a 15-minute interview. So a lot of writers didn’t have time or the desire to do it. Now also with some of these writers, you need a lot of material. And if you’re just starting out, you may not have enough material for a Playboy-length interview. So there were some instances where I wanted to interview younger writers and it just didn’t work out for whatever reason. But I’ll give you one example. There was one of my favorite sitcoms is Modern Family. The writing is absolutely brilliant in that show. And there’s a young Asian American writer named Elaine Ko that I tried desperately to get and she just never got back to me.

It was frustrating because I have a daughter, she’s in the comedy and no way do I want this to be a white middle-aged men’s club. I had a stick up my ass about that for years because I didn’t know anyone. And I don’t want it to be an elite club. I want it to be open for everyone. The best comedy now I see is being done by those who aren’t white, middle-aged American, like “Pen15.” I don’t know if you’ve seen that show, it’s just a work of brilliance. But I guarantee, I mean name any writer, whether it’s Tina Fey or whomever, Chris Rock. I tried, boy did I try. And they just said, “No.”

Independence is a huge theme. And you mentioned that in a lot of these interviews, writers finding success by essentially doing it their way. There’s always an interesting tension between the creatives and as you say, the gatekeepers, whether it’s the networks or the suits or the execs, I guess there’s no surprise there, but what is it about comedy that people think it can be so easily commodified?
Well, it all comes down to money. If you can put out what you want and make money from it like “Modern Family,” or “The Simpsons,” it’s such a miracle because it never happened or very rarely. It’s an early “SNL,” or National Lampoon. But usually what I found is that the best comedy is not done for money and doesn’t necessarily produce money. It’s done for very individual reasons. And I’ve also found that the gatekeepers, whether it’s the executives or the producers, oftentimes don’t have the same sensibility as the creators. Their sensibility, their humor IQ, may not be the same as those who are creating. And they may want to go more middle of the road, more “Two and a Half Men” than “Pen15.” It’s like music. Alternative music isn’t going to bring in as much as more mainstream music, but more mainstream music doesn’t necessarily interest those who want to do something interesting.

And what’s alternative ultimately becomes mainstream and then loses its edge.
That’s right. I mean, it takes time for something to become big. And if someone doesn’t understand it, if it doesn’t exist yet, it’s hard to convince them to do it if it’s brand new.

So obviously independence is important to you. How do you square your desire for independence while working at a notoriously stodgy or at least old school place like Condé Nast?
Vanity Fair has always been a little different. It’s been a little more open. Graydon Carter used to be the editor came from Spy Magazine, which I read growing up. Susan Morrison is now one of my editors at New Yorker, and she’s incredible. She was one of the founders of Spy, one of the founding editors. So there was a freedom there when it came to comedy that you wouldn’t necessarily find at Vogue. But it really comes down to another piece of advice that I give young writers is: If you want to do what you want, you have to have a two track system. And that is one track, make money to live and to have insurance and the other track to have the freedom to write whatever you want, not necessarily for money. I knew a lot of comedy writers who had to make a living at comedy writing they didn’t like. I had a friend who wrote for “Shit My Dad Says,” and he was miserable. He didn’t get into comedy to write that. But you find yourself having to do that because you have to put food on the table.

But I’ve been lucky enough to be able to work, say a dryer job in editing and writing that allows me to do whatever I want on the side. And quite frankly, it also allows me access because a lot of these people that I reach out to, they don’t know who the hell I am, but they know that I work at Vanity Fair and that to them is an in that helps me have access to these people.

There’s a sophistication to your interviews. You have a very nuanced to expertise about comedy, you know your shit. You know what questions to ask, how it’s made, its history. Some of your own comedy can be quite broad and really silly in the books. Who did you love growing up?
When you say broad, that’s interesting. I don’t consider it broad at all. If I’m satirizing a broad type of comedy, like trucking of CB movies, then I think it’s broad. But I think a lot of what I grew up liking was very dry. Whether it was Albert Brooks, whether it was Woody Allen, whether it was Merrill Markoe who was really the voice of early Letterman, David Letterman. But most of what I like is not even comedy, whether it’s Richard Yates or Emily Dickinson or Vladimir Nabokov or Borges. I think more things can be learned from things that aren’t comedy and learning from writers who produce things that were funny and maybe a deeper vein, a deeper record.

Nabokov could be hilarious.
Yes. I mean, if you read “Lolita” or “Pale Fire,” which could be I think the most brilliant book ever, it’s so brilliant I don’t know what the hell’s going on. But it’s almost like a futuristic society, a higher mind has written the thing. Borges, to give an example was just brilliant. And what he was doing was just years ahead of McSweeney’s and everything else. He wanted to write a book, but he didn’t want to write the whole book. So what he did was he wrote a book review on this fake book. Well, I read that as a kid. It’s like, what the hell? It’s not too different than writing a novelization on a non-existent movie. That’s where I learned to do that. It wasn’t from comedy, so it was always very dry comedy and never really too loose. Albert Brooks in particular, I think is just a genius. If you look at his early movies and his standup way ahead of his time, I think is still not really understood, or he’s not understood in Hollywood. He’s not getting opportunities like a Jack Attell would get, which I just find incredible.

That’s crazy to me. Why is that? Is he hard to work with? Because I mean, I agree. I think he’s brilliant.
I think he’s brilliant, hard to work with, and he may not bring in the money. I mean, all it takes is one or two movies that aren’t huge hits, and it all comes down to money. But I do think, too, that if he were willing to do it, he could do whatever he wanted. He could have a podcast. He could put out his own TV show. I mean, there’s opportunities now to do whatever the hell you want. You don’t have to wait for permission anymore, which is really great for everyone.

You also have a podcast, which you’ve had for a while, but you just relaunched it or reconfigured it.
It’s not weekly anymore, biweekly, it’s now monthly. It’s just whenever I feel like doing it. It’s on The Sonar Network, and I’ll interview people when I feel like it. And each episode contains found footage, audio footage that I collected when I was going through my Fat Elvis period in New Orleans in the ’90s, where I would just listen to radio and watch cable TV all night every day. It contains a lot of found footage and audio, and each episode contains a short bit sketch, I guess like Old National Lampoon Radio Hour.

Yeah. Your current one has a bad hostage negotiator, as the sketch.
I always wonder what I’d be like as a hostage negotiator and it doesn’t end well. This is what happens.

A lot of the writers you talk to in your interviews talk about the writer’s room, the communal nature of it, the stress of it, the joy, the speedy deadlines and all that. But then there’s also the lone wolf comedy writer, which is the camp I’m guessing you fall into. Is there a fundamental difference, temperamentally, between the lone wolves and the collaborators?
I got into writing comedy to be a member of a writing room. I mean, to me, what I grew up seeing and reading about, whether it was “Your Show of Shows” or early “SNL” or “Letterman” or “The Simpsons,” that seemed like a dream. Being in a like-minded room, shooting the shit, telling jokes, it just seemed like the best way to live. And so that’s really why I got into it. I ended up becoming just a solitary writer for print because I found, and I’ve been in a few rooms, that it’s tougher than it looks. And a lot of jokes that you come up with aren’t accepted. And you really do have to be a very social open person to sit in a room for 10, 12 hours a day saying, “What about this? Or how about if we do that?” Writing for the common good.

And I guess I got a little spoiled over the years and that I could put in whatever I wanted. Whether it works or not, I don’t have to answer to anyone. The money isn’t as much, but there’s full control. And I don’t know at this point, even if I was asked to be a writer on a show, if I’d be capable of sitting in an office for however many hours ordering takeout food every night. I think I could have done it when I was younger, but it definitely takes the type of person who can work well with others and who hasn’t written alone for 25 years. I think I’m too set in my ways.

Check out this episode of “Brooklyn Magazine: The Podcast” for more. Subscribe and listen wherever you get your podcasts.