How do you write a joke?
Comedian Josh Gondelman explains how to win multiple golden trophies to lord over your enemies
First, a few things I enjoyed this week:
• As a devoted fan of Carl Franklin’s cult crime thriller One False Move, I was overjoyed to see it getting a Criterion release and reappraisal. I was also a bit disappointed, only because it would have provided valuable information for my research in crafting the podcast episode I did on it years ago with director Julia Hart for my old show, Switchblade Sisters. But now we get to enjoy hearing from Franklin himself on how he crafted this unforgettable ‘90s neo-noir, and so far my favorite interview has been this one with Matt Zoller-Seitz for Vulture. In it, Franklin explains his process for working with his writer, who is also his star (Billy Bob Thornton) and how he fought for Bill Paxton, but my favorite part is the exchange that begins with Franklin talking about how and why he favored long shots. It’s a gorgeous film, and you should watch it after reading this interview.
• As a newbie to substack, I only just started subscribing to and reading people’s work here, but author Lincoln Michel’s page, Counter Craft, I’ve found to be invaluable. I caught up with an older piece of his from July on author Henry Hoke’s novel Open Throat, a first-person account from the voice of a gay mountain lion wasting away in Los Angeles. I’m sharing this particular interview, because Hoke is both pointed with how he writes but also poetic in his explanations of how the words arrive on the page. It combines the process and the magic quite nicely and makes for a good read on contemporary novel writing that exists just outside of the mainstream.
• I have mixed feelings about Clint Eastwood as a person and a creator, but I’ve always respected his abilities as a director, even if I do not particularly enjoy a film I’m watching. He appears to be both professional and respected by cast and crew alike. In this behind-the-scenes featurette for The Bridges of Madison County, we get to hear from Meryl Streep and various crewmembers exactly how he works, and although a featurette’s purpose is often to just puff up the director and give them their flowers—deserved or not—there is genuine sentiment in these interviews that signifies these people mean what they say. In particular, I love how Streep explains that Eastwood removed what would have been his own Oscar-worthy moment, because it would have shifted the focus in a scene too much. And I also love Victor Slezak talking about the well-oiled machinery of an Eastwood set. It’s definitely worth the watch. (I have further feelings on the degradation of the BTS featurette and how they are rarely any good anymore, but I’ll save that for another time.)
Secondly, I love hotel bars, and lightly haunted hotel bars are even better. I met comedian and writer Josh Gondelman in one such bar in the Poconos, when both of us were performing for the podcast network Maximum Fun’s annual Con—me promoting my old podcast Switchblade Sisters and him entertaining the masses with standup. Gondelman is so immediately approachable, one may not even realize he has a room of golden trophies for his writing (Last Week Tonight with John Oliver, Desus & Mero, etc.). His standup sets, too, are approachable, but in a way that quickly disarms you before offering its surprising sharp edges. There is a sense of him in his varied comedy work that he is “the good boy,” and yet, if you have seen any of his late-night writing, it’s doubtless he can go to extremely dark places. I would describe his comedy as “inclusive,” in that he does the work to make sure the most people possible feel like they are in on the joke
I wanted to know more about that work, so I asked Gondelman about how to write a standup set, how to break into television writing, and when it’s okay to have a little bit of ego.
Where do standup sets come from?
I usually start with like a crystal from the last set. If I want to start a new hour, I don’t start tearing the old hour down to the studs and start from zero. I don’t tour at that level and don’t have that platform where I know if I star from zero people will come see me, trust it will be good, and support me through this process, so it’s a process of muscling out the old stuff and filling the space with new stuff.
The last special was a special case. There was a bunch of old stuff that was in there I had done on previous albums, because it was assembled very quickly as I was starting to do live performing after everyone was vaccinated—well not everyone, but the people who did. That set got kind of got cobbled together—that makes it sound haphazard, but it’s not. It was a medley of stuff I’d worked on in the past and new stuff, so when I was done with that, there were stories and jokes I’d told that were so old at that point that I was like, Whoa I think those are fully retired unless I have some specific themed or corporate show I have to break them out. It sometimes goes first in first out, because the jokes feel temporally relevant, so it’s like this is the last stuff I’m working on and it daisy chains to the new stuff, because I wrote it during a similar part of my life, and sometimes the closer will stay, because it’s hard to figure out what you’re building to until you know what you’ve built with standup. So sometimes the closer will get replaced later in the game, where midway through writing the new hour, I’ll say, This is capstone of the set, and I’ll build backwards from there. It’s hard to feel like I know where I wanna come down with a new set of ideas that I’m developing show to show.
How do you know your closer is your closer?
There’s the traditional comedy-set structure wisdom: second-best stuff goes at the top, best stuff goes at the end, and then good night, and I do think there’s something to it. I like to close often with something that feels a little more substantial, something I take a little more time with, not necessarily the longest piece in the show but something that feels like building up to a crescendo and then leaving on a high note. If it feels like I don’t want to follow it with other stuff that’s really helpful. Like this goes last because it’s the last idea I want to express, the taste I want to leave people with in their ears and brains, to be synesthetic with it, the feeling I want them to leave on. Sometimes you go, Hard for me to follow me after this!
What’s one basic necessity for a standup act?
When you start you’re only doing—some people start doing less time than this—I was doing 5, 7, 15-minute sets as I started to work, so there are certain things that are incumbent upon you to communicate faster when you have less time. It’s a little different when you don’t have any people coming to see you on purpose. You have to establish yourself a little quicker and set a baseline for here’s who I am, and I feel a little less pressure to do that now, where I still wanna set the tone for what the hour is gonna be, but I feel a little less pressure to open with something where I’m like, I, a guy you probably never heard of, am like this… in one sentence that gets a laugh at the end. At the Comedy Cellar, I feel a little more stakes to doing that up top still. On the road headlining, it’s nice to have the feeling that enough people are there because they’re familiar with my work that I can—not be sloppy—but that it doesn’t have to be such a broad depiction of myself to get people to think, ah he’s one of those guys.
One that I used for quite a while—and still occasionally break out at a place like the Cellar—I’ll come out and say, “I’m like if a cardigan were a person.” I found that to be very effective. I said it on The Late Show with James Corden. It’s such a short way to get a little laugh and for people to know your sensibility, and it’s providing a lens for people. It’s its own joke, and it’s not the strongest joke in the set, but it goes at the beginning. I wouldn’t necessarily say it later in the set, because you’ve either got the point of what I’m gonna be like, or you haven’t, and it doesn’t bear the weight of doing it 30 minutes or 15 minutes into the set.
How did you transition from standup into TV writing?
I had been working towards that for a number of years, and I’d been applying to shows. You do a submission packet of requested materials that are specific to each show you apply to, so before I had any kind of representation, it would be reliant on knowing a friend who worked at a show or having met someone who’s a manager who didn’t represent me but who I was friendly with, who would do it as a friendly arrangement. And if it worked out, then we’d work together on the deal. It was knowing the right people, so I was getting a trickle of these opportunities. I was on the verge of signing with a manager who was a friend of mine when a different friend and I had Twitter success with a viral parody account, when that was a thing that someone might create. That popped pretty hard and got me in a situation where I could apply to these jobs more consistently. When they were looking for writers, the packet would come across my desk with more regularity, so I did a ton of those. In 2013, I did 19 packets, which resulted in one paid gig that was very brief—two days of freelance work—and the last one that year ultimately got me my first full-time position, but not in the writers’ room. I got hired to do social media and digital content for a late-night show, and then after the first year, I ended up being moved over to a staff writer. When I was first hired, I was like nine on the list of eight that they could hire, so it was a matter of sticking on at this different job until I got hired.
How are writing for these two forms of comedy different?
Writing for TV, you’re beholden to many needs that are not part of the standup set, especially for a late-night show. You have to be responding to something that’s topical often, or something that’s outside of your own voice. Those challenges are really fun to work on, to refine those skills. The two big challenges are that the structure will be more formal, because it has to fill a certain vessel in terms of timing and tone and content. And then the voice—especially in late night—is already fairly well defined. Again I enjoy doing that. The end result of standup is it can be whatever you want. But I love being a part of something that is bigger and more layered and has more production behind it and a bigger reach than the stuff I’d be able to do on my own, and I like being a part of a team. I do still have this itch to say exactly what I want, and if it’s good, then I did a good job, and if it’s bad, then it’s bad, and I don’t have to be accountable to anyone else. But that’s why I do standup.
How do you write for another person’s defined voice?
I think it’s familiarity with their sensibility from having seen their work, and ideally you write for someone you enjoy their perspective, and then it’s like hopefully you get helpful feedback, like, Oh the host really likes this other kind of thing, where it’s a hard sell to get them to do this other kind of thing. You learn by doing in some ways. It’s hard even when you come to a job, where you’re very familiar with the host’s perspective, and they go, Oh yeah oh I don’t do that. And you’ll be like, I didn’t know that was a rule, I was just thought it was maybe something you hadn’t gotten to yet!
Do you feel like you’ve been able to add little touches of yourself to other people’s voices?
I think that’s the most gratifying stuff, is not just being able to fully slip into someone else like you’re doing an impression of them, and I think that as someone who has managed a writers’ room, too, what you want is somebody who pitches something that’s like, I never would have thought of that. That’s what you want when you’re looking at submissions. You don’t want somebody going, Oh this could have been on last week’s episode and it would have replaced this other similar joke. You want, You really get the kind of thing we do and you hit it from an angle that no one else here would have thought of. It’s very fun to get opportunities to do that. I wrote for two shows that were very different from one another, both in terms of structure and the hosts and their comedic perspectives, and I brought my own flavor to those writers’ rooms, because I’m the same guy, but the direction of where I dragged the show in was kind of opposite.
When writing so much for other people, do you ever get an identity crisis?
There are periods where I’ve been very invested in working a job, but other times I’m wondering what do I have to say. I’ve been really lucky to get to do so much standup in New York, even when I’m working. I’ve written books (You Blew It!, Nice Try) I can pitch freelance stuff to outlets, and that’s when I get to search who I am and what I want to talk about. There’s an ego thing about it, too. I wish I could be more ego-less. You know how sometimes people are like, Here’s what I’m like, and you’re like, Oh, you’ve never met you. I think I do a good job of not obliterating myself from the work but obliterating my ego from the process to a fair degree, so I try not to get attached to my idea like it has to be this perfect snowball I packed into exactly the shape of my hand, and everyone will know. I try to serve the project I’m working on in a way that feels organic to what I think is funny and fun about that project, but I do have enough sense of artistic ego, where I wanna do stuff for people to say, “Hey I like that thing you did!”
What are the actual nuts and bolts of how you build a joke?
I will often run ideas by Maris [Kreizman], my wife, and I think she has a really great sense of humor, and can tell me, Yes that is funny and makes sense or No I don’t know what you’re talking about or Yes that does make sense, but it’s not funny. Those are the three options. My friend Alison Leiby and I will kick jokes around together. At this point, I record something and maybe I have a couple tour dates before this set is public, and I can still do the old material while I build up the new stuff, and it’s like 8 to 10- to 15-minute sets in the city. When I do those sets, I’ll respect the audience’s time and producer’s time and not open mic fully through it, but I will sneak in new stuff. If a friend says, “Hey, will you do this show at a bar back room, where 12 people will be there,” I’ll take a few more risks. Maybe 7 minutes of a 10-minute set will be new. If I’m at the Comedy Cellar, it might be like 2 minutes that’s new, but “new” meaning I’ve already tried it and know it works well enough to take to the club where audiences are paying $25 and buying two drinks minimum.
How do you literally write your standup sets?
I write longhand in a notebook when I’m working on jokes and will usually do a bullet-point set list in my notebook or on my phone to remember what I want to talk about. I usually overwrite, and I’ll think, “Man, this is gonna be a great 4-minute chunk,” and then I’ll realize it’s actually a 1 minute 50 second chunk. I pare it down to what resonates or doesn’t feel redundant. Then I can kind of fill in, either by sitting back down with the frame I have now, or I will keep doing it on stage. But once you know what the pacing and rhythm are—where it hits the audience what to expect—I can listen to myself and react to me and riff in a way that I don’t feel like I’m panicking, thinking of how I swing to the next vine. I know where the next vine is, but if I want to swing on a longer arc, I feel comfortable doing it, and stuff fills in there organically. And even beyond that once I start putting this new stuff into the context of the new set—whether 15 or 60 minutes—then I can go, Oh here are the connections I’m drawing and here’s a the way to call it back, or synthesize it with thematic unity. Sometimes I’ll say, “I didn’t realize I was talking so much about this idea,” and I can round that into shape, and that’s a fun part of the process, seeing how everything settles into place and finding new connections.
What are some things you didn’t realize you were fixating on until they showed up in a set?
There was a period with this new hour, where I had three jokes that mentioned remote controls, and I was like, That’s so weird. What a weird touchstone I keep going back to. Is it too much, a motif, a different reference point? It was very funny to realize I had these three jokes I wasn’t doing all together, and then when I did them in a full hour I was like, I keep saying the words “remote control.”
One joke is about my parents and how if they have to learn to use a new kind of remote, television is over for them. One of them is a joke about making enough money, where when the batteries in my remote control died, I throw both batteries away at once instead of replacing them one at a time. Different contexts, but why is a remote control the touchstone for both of those contexts? Initially I was doing the jokes in different, smaller sets, but when I did them both in the same show, it became noticeable.
I know a lot of standups—and writers in general—like to go to therapy, but it sounds a little like doing standup can work out some unconscious thoughts. Is it a little like therapy?
There’s a way to do it where you’re very reflective of yourself, but if you’re doing it in the way that people go to therapy, with no goal except for to explore and learn, it’s definitely more for you than for the audience. I do find the action of doing standup, the activity of performing, to be therapeutic but not therapy, more like physical therapy than mental therapy. For me, doing a set is very stabilizing in the same way that when you’re in personal turbulence, sometimes it’s nice to just occupy yourself with a task. I have a good handle on standup and how to do it, and it’s a set time. I’m not on the internet. I am present in the moment doing this thing I’m doing, and it is a mentally immersive.
You said before you can get to a place where you’re listening to yourself, like you’re outside of yourself.
I really like getting there. It’s so fun to me. I know how the jokes go, but it’s actually because I know it so well. I’m feeling it rather than just hearing how I sound. I hear what kind of reaction a joke engendered, and I can react upon it, and it feels so safe, in that I’ve built out a significant chunk of this bit, but it’s also adventurous, where I can go, Oh I haven’t gone down this path before and I can explore it, because I know the way back.
So there’s an element of feeling safe in the work.
With TV writing, the safety is partly working for someone else, where you get to take these risks—unless you’re the boss. I remember I pitched a joke at a job, but my boss said, “This Anne Frank joke you pitched is very funny but obviously cannot go in the show.” I said, “Thank you for the kind words. My job is to write the funniest jokes I can think of, and yours is to tell me when they can’t go in the show.” There is a freedom to someone else’s expertise guiding you. It’s harder for you to bomb when it’s somebody else making the final call, so there’s a much more rigorous vetting process than in standup, where you say, “I thought this was funny, so I said it three hours later.”
But sometimes you are the boss.
That’s the opposite. I get to benefit from other people’s good work. Sometimes I’m not even looking for the biggest laugh. It’s like, Even though it’s not the biggest laugh in the piece, I think it’s so funny and engaging, and we’re keeping it. Making those calls is really fun, but it’s again just being fully outside of myself in those cases. I don’t know if I’m the kind of person that could make a good feature writer in the dark. I gravitate less towards big projects where I don’t get to collaborate with someone. When I have to do all of it on my own before somebody else sees it, I think standup more appeals to my inclination to be like, Is this anything?! What do you think about this? And to have it live or die in that moment.
As a writer, I would rather hear, “I love this, but it doesn’t quite work for what we’re doing,” than, “I don’t like this, but it’s what we have to go with.” One of the executive producers at my first full-time job was Tim Carvell (The Daily Show, Last Week Tonight with John Oliver), and he’s so thoughtful about making sure a joke does the work you want it to do. I was working on a weekly show for him, and he made sure we were gonna make the time to make sure the jokes we were using did what we intended, where I’ve heard shows with a faster cadence are like, We tape this in two hours, it’s as good as we can get it. Still, I describe myself as the “king of good enough.” My wife is the opposite, so precise and thoughtful, and you can see her really giving the same energy to a first draft that she would give to a final draft, because she doesn’t want to put it down on the page until it feels right. But I have an easy time being, Clickity clackety click, that’s enough words and I’ll fix them later. That’s future Josh’s problem.
There’s an accordion motion to my writing, like I overwrite and then get rid of all the stuff that doesn’t work. I’ll eliminate the things that are too indulgent or irrelevant, and then in the next motion, I’ll fill it back in. I also like sitting on something for a little while and then coming back to riff and expand upon it as if you’re in conversation with this previous version of your own work or yourself. You’re less in the process of doing and more knowing what a different person would hear or see. That’s so helpful in communicating to be like, Now that I forget the exact order of these words or I remember it so well I’m not thinking about it, I get to experience it like someone else hearing it.
As we get older, we forget faster.
I forget as I write! That’s the goal, to have that perfect blank slate at the end of every sentence, just a full Memento-ization of the creative process.
Is it scarier to write something like a book then? Because it’s more permanent in a way?
Putting something down scares me less than not having an audience or another voice to bounce things off of. I co-wrote my first book, and I worked closely with my editor on the second one. I was sending my editor Stephanie three chapters at a time. Even if she didn’t write back right away with notes, it was a good feeling knowing those were safe with her. I was like, I trust that she has them and she’s thinking about them. It was such a relief to have someone I trusted I could send pages to and know and know that someone had considered them.
Is there any advice you have for people, or, rather, any reflections you have on the trajectory of your career and ways you wish you could have done it differently?
The job where I pitched the Anne Frank joke, that was a punch-up job, where I would send in a lot of stuff remotely, and it wouldn’t get used. And I’ve had to learn to trust that if I were doing a bad job and needed to change, they would tell me. I will trust that if they hired me, they’re getting what they want from me, and I can’t allow myself to spiral, like, Why don’t they want more? I was very proud of myself for getting to that point. I’ve had jobs where you are made to feel that if you’re not getting a lot of stuff in, you’re not doing it right, and others where you don’t know the expectations. So on one end of the spectrum, I’m writing every word of the script, and on the other I’m getting shut out entirely, and I don’t know where I’m supposed to land. That’s also what I mean by the “king of good enough,” by the way. There were a couple things I’ve published, where I’m like, Oh I should have done more, but most of the time it’s about getting out of my own way and not holding myself to a standard that’s impossible, given time restraints and resources. I’m pretty good. This is how I perceive myself, pretty good at the work and easy to work with, and I have an “I’m a real pleasure to have in class” attitude.
You still feel this way even after winning several Emmys?
Well, it’s the collaborative effort. I have been so fortunate—truly I don’t mean to sound braggy about the amount of awards I’ve won—by being part of a wonderful team of incredible people given the resources to do the work they’re capable of. It’s beyond anything I could have hoped for. It wasn’t like, Gosh I’d like to win a bunch of Emmys and Peabodys and WGA awards. It’s a hard thing to shoot for. It’s the whims of the voting public. It’s mostly validation I got to be a part of this wonderful thing with so many wonderful people across departments… Okay, but one time I got a very mean Facebook message from somebody, and I try not to big-time people on Twitter, like I know what I’m doing cuz I got all these accolades. But a stranger on Facebook messaged me, like, Maybe you should look for a backup career thing. It didn’t hurt my feelings, but I was just annoyed, because it’s such a hacky thing to say. So I wrote back: “I have a room full of golden trophies that says otherwise.” It’s very fun to be an ego monster when there are no stakes, and you’re not hurting anyone. No response from this guy after that, by the way. It’s so insufferable, but it was so funny to do just to this guy to be so self-aggrandizing in a way that is not visible to anyone. It’s something I rarely feel the need to do, because I don’t feel like people should know who I am or that I have a reputation that should precede me into every room or something. I don’t know if I’m good, but I know I succeeded. If you don’t think I’m funny, and your response is, “Uh, too bad you never succeeded,” I can guarantee there’s no way you’re as successful as I am. It doesn’t matter if I’m good. If you’re a chiropractor, you don’t have as many chiropractor awards on your wall. I did a good enough job that they want to keep me around and think I’m a valuable contributor.
