Getting ‘Positive Reinforcement’ From Josh Gondelman

It was before People Pleaser came out, because we recorded that summer 2021, so I’d already had a year’s headstart by the time it came out. There’s usually a three-month dip after I record something where I’m like, “Well, there’s all my ideas, never going to have a new one.” Part of it is just from the process of having gone through getting something recorded, I’m locked in and not having as many new ideas. And part of it is that I’m still editing and looking at the old stuff, so I can’t fully embrace new stuff. With Positive Reinforcement, I recorded it last June, and then had three months of “Oh, everything I think is bad and not funny,” and now I’m halfway to a new headline set, which feels really nice.

A big difference between your preparation for this hour and the previous one is that this time you weren’t also working, I assume pretty intensely, on a late-night show. How did that change your process?

There were a couple of big differences for sure. One of them was that I was just able to go on the road a lot more and tour around the country. I mean, it wasn’t working on a late-night show that we were putting out one to two episodes a week, but also nobody was working on TV writing projects, really. It was a weird summer. The strike effort was obviously really heavy and intense and a worthwhile thing to have undertaken, but it was like, picket, picket, fly to Sacramento, train to San Jose, fly home, picket, picket, train to D.C. That was summer 2023, and I was really heavily on the road from 2022 to 2024. It was very gratifying to get to go to all these places, some I’d never toured before and some I hadn’t been in a long time when I was in writers’ rooms. 

The other thing was, the special that I shot in 2021, I had just started doing in-person shows again post-vaccination. So that was really weird, and that special ended up being, I would say, two-thirds new material that I’d never recorded before, and one-third greatest hits that I’d done on audio albums, but never recorded video, because I had to ramp up so quickly from doing an occasional Zoom show over a year to recording my first video special. So those, I think, were the biggest differences process-wise, for sure.

When you put an hour together, do you have a through line in mind?

I really admire people that are like, “I’m going to write a show about my relationship to my parents” or “the romantic tribulations of my life,” whatever it is that feels like a really strong angle for people. I usually start writing and then identify what the themes are after I have 20 minutes or so. And for Positive Reinforcement, it really felt like what I was thinking about was post- the isolation period of the pandemic, going back into the world and being like, “I feel generationally different than I was coming in,” and really thinking about how to be a present and engaged person in the world rather than just being the kind of guy that’s like, “This is new, and that’s why it’s bad.”

You’ve formerly said in interviews that you don’t do topical jokes because you had Last Week Tonight or Desus & Mero to do that. Were you ever tempted to dip into topical jokes more this time?

I’ve shifted around a little bit on that, especially since I’m not in late night and I did some in my last audio-only album, Dancing on A Weeknight. There was a little political stuff that felt a little time-stamped. But even since then, 2019, there’s been such a shift in distribution mechanisms. So I do think when I want to do topical jokes, it’s the kind of thing where I can do a few at the top of a set and film them with my phone and get them out online as we go. And so, there’s a bunch of that stuff on my Instagram and TikTok. 

But also, a couple of those things, stuff that felt at the time like it was going to be super-topical, I was ultimately like, “Actually, this feels stickier to me.” So the whole chunk at the top about why we expect corporations to share our human values — that started out as a thing I thought was topical. I just saw a bunch of people being like, “Best Buy, speak out!” and just being like, “What do we think Best Buy’s politics are?”

Plus, the news moves so fast now that by tomorrow it’s already old.

That, to me, is the fun opportunity that comes from high-quality or fine-quality video being at your fingertips, and a distribution network being right in the palm of your hand at all times. I can do a joke in Oklahoma City on a Tuesday night and have it on my Instagram and TikTok by Wednesday morning, and that’s a fun way to feed that furnace that’s constantly demanding — “demanding” is a strong word, you can opt out, but constantly requesting fuel.

And it gives the audience an idea of what they will see that’s going to be different.

Yeah, definitely. It’s stuff that you don’t have to burn, which I like. That’s why so much crowd work is what you see — because it’s not stuff that you’re going to replicate on the next show. If I’m doing a really topical joke over a weekend, then it’s fun to put that out on a Monday and go, “This is what I was working on this weekend.” 

I think I was in Bloomington, Indiana a couple months ago right after the Cory Booker 25-hour filibuster, and I worked on a little joke there. I ultimately posted the version I got on a tape from the Comedy Cellar back in New York, but it was like, that’s the kind of thing that, if I record an hour a year, a year and a half from now, it’s not going to make it to that unless it really blossoms. So that’s a nice thing to get to share, and I do. It’s nothing against topical jokes, it’s just like when you put a topical joke on something that comes out two years after the topic was in the news, you really have to make sure the bit stands up outside of that context.

Since we’re touching on your former work in late night: We seem to be witnessing the genre kind of driving very slowly off a cliff. As someone who has worked on two of the most beloved late-night shows, what are your thoughts on how things are going?

I’m so grateful for my time working at Last Week Tonight with John Oliver and Desus & Mero, really fun, wonderful jobs and shows that I’m really proud of. So much stuff we got to do on TV and that John is still doing, it’s really cool to see that. I left a long time ago, but it’s like, man, he’s really built that show and the team has really built that show into an institution. I think I kind of am constantly ping-ponging back and forth between “late-night TV is a robust feature of the television landscape” or “is fading,” but also there are so many people still doing good work. I have a bunch of friends that work for Seth Meyers, and whenever I see the stuff that they’re doing — I’m not up usually at 1 p.m. watching, but I see the stuff the next day, and man, they’re so creative and fun.

But the other thing is, everything is late night. When someone from Netflix — I think it was Ted Sarandos — goes, “I could see us acquiring exclusive rights to premium popular video podcasts,” it’s like, that’s late night to me.

There’s a disconnect there where I just don’t know how to bridge it industry-wise. It feels like there are fewer comedy films than ever before, right? It’s not just late night. There’s less industry push and investment behind comedy, but stand-up comedy — I don’t have statistics, but it feels statistically accurate to say stand-up comedy is more popular than it’s ever been in history. There used to be more comedy clubs. You can talk about the boom of the ‘80s, but it wasn’t like there were, whatever, 12 different comedians filling Madison Square Garden every year. That didn’t used to happen.

In terms of investing in comedy, the Taylor Tomlinson situation suggested not only that CBS, one of the broadcast networks, doesn’t have enough money to throw at her to make her stay, but also that it didn’t have the will to find someone else to host that would’ve kept everyone else on the show employed.

That’s the thing that really gets me. There’s always going to be a host of a late-night show, which isn’t necessarily a big income driver for these networks and streaming platforms, who outgrows the platform that they’re on, whether it’s because they’re exhausted from the grind of daily TV, or they feel like they’ve said all they had to say, or they’re just like, “I have bigger, more exciting opportunities elsewhere.” 

That’s always going to happen. But to me, it’s also that these platforms are only interested in someone that’s too big for them. It’s not worth it for them to cultivate new talent and develop it. That’s a real bummer. It’s not like people don’t like jokes or that there isn’t a robust bubbling-up of comedy stars-in-waiting to host these shows. It’s that, on the industry side, they’re having a hard time getting eyeballs on the things that they’re putting out into the world, and that none of them want to do the work of developing new artists. Everybody wants to look at Instagram or TikTok, see a big number and go, “That’s our taste. Our taste is Big Number.”

And that’s so demoralizing. I hate to be rosy-eyed for the past, but I definitely feel like there used to be more of a widespread pretending at least that people had taste or that taste mattered. And it wasn’t all just like, “No, most is best, and if we can’t have most, we will have nothing.” Okay, everything has to scale infinitely now. 

I’m sorry, I’m being so unfunny and preaching.

I started it.

It’s a labor issue. It’s an issue of structure within these corporations. It’s just such a drag to me. And nothing against Taylor, who I wish all great success post-After Midnight and is so funny, but that was a crazy thing. 

I don’t know if you watched the Conan O’Brien Mark Twain special that was on Netflix, but so much of what everyone was saying about his early days on Late Night and how long it took him to figure it out and get good and then great at it — it feels like none of that could happen today.

No. And none of it happens with any show. I think about this all the time. It used to be if a season of a show, a 30-minute comedy, ended after six episodes, you’d go, “Oh, that show failed spectacularly.” And now networks are ordering six episodes of a show — and not as summer replacements or as a tryout. Girls5eva is one of my favorite shows. Netflix acquired the rights to the first two seasons and then made a six-episode third season that didn’t feel like it got any push from them. And then they were like, “Well, that’s enough of that.” And it’s like, you spent all this money and effort to acquire the show, greenlight a new season, and then you gave it a total of one Marvel movie’s worth of hours, and then they were like, “That’s it.” 

Stand-up is one of the only forms of writing where you also entirely control the performance. What benefits of that do you feel the most keenly?

I love it. I really love the balance between working on jobs for other people and doing stand-up and getting to say exactly what I want to say. I love the feeling of sinking and swimming on my own merits on stage. That is very thrilling. I love getting to have an idea and going, like, “Is this good? We’ll let the audience weigh in on their opinion.” Then I can decide if I feel like it’s still worth doing if it gets a medium response, or go, “Ooh, this really feels like a rich vein.” 

What do you miss the most about writing with a team on a show?

I just miss regularly getting to work with people who have better ideas than me or different talent than I do. I write jokes with friends from time to time, we’ll bounce ideas off each other and stuff, but there’s really something special about being in a writers’ room and coming up with an idea and it almost being there and someone going, “Ah, what about this?” And you go, “Oh, this is great.” Or getting to do that for someone else or even just being inspired by the work that other people are doing collaboratively near you. 

And I do miss working on stuff that’s bigger than just what I can generate alone or what I can pull a team together to create. So I’m definitely looking in the future toward figuring out what the next TV opportunity is, now that this is ready to be out in the world and I’ve toured it so hard and stuff.

I’ve really enjoyed not having to wake up and go to an office and sit in an office all day. I love the work itself, but in the last couple of years of mostly touring and doing independent writing projects and working on things short-term, I do like that I don’t have to be a place at 1:30 p.m. even if there’s nothing for me to do there, or even if I have 45 minutes unstructured where I’m like, “Man, it would really help if I could go pick up my dry cleaning right now, but I’m 10 miles away from it.”

You have a joke in the new special about anti-Semitism and how you wouldn’t say criticism of the state of Israel qualifies, but that criticism of Adam Sandler does. Talk more about this, because I think someone has to be a real hater to go after him.

Especially now. There was a period when an Adam Sandler movie had the cultural resonance of like Nickelback putting out a new record or whatever. But now I think people, myself included, have come around more. I grew up really loving his early movies, and my friends and I had his records when we were way too young to be listening to them. I had the experience of all my friends getting those albums confiscated one by one by parents who heard 10 seconds of one, and then having to bring a boombox out into the woods to listen to them. It’s so important to me. 

I mean, sadly, this was a joke that I wrote, I don’t know, a year and a half ago that still feels very relevant to the ongoing tragedies that we’re reading about every day. And so, I wanted to say something that was pointed and real. I was on the road, and it really felt like this was occupying so much of my mind, just what’s happening in Gaza and the real cruelty of the Israeli government and military toward Palestinian people. “Cruelty” is such an understatement, but I wanted to say it in a way that maybe I got to make the point but didn’t push people’s faces down into the horror of what’s happening.

And so, I think trying to figure out what the silliest version of anti-Semitism was as a counterpoint, and I think Sandler got there, just someone being like, “I just never thought Happy Gilmore was funny.” “You might as well have shot me in the heart through a bagel!” That’s how central that is. And then there’s accidentally two Fiddler on the Roof references in the special. I almost cut one just because that’s weird.

Rewatching People Pleaser before Positive Reinforcement, I was delighted to see one of your other running themes is the Dropkick Murphys. Talk about their importance in your life and art.

Yeah, I mean, it seems like they’re really great dudes. It’s just, especially the one song from the soundtrack of The Departed is so comically Bostonian that people associate it with the city. That is, I’d say, their most famous song, and it’s explicitly about Boston and it was so big and it was such a core thing — at sporting events you’d hear it and it just feels like such a perfect touchstone for the city. The sound of it is so boisterous and aggressive and conjures such specific imagery. 

And so, it’s just such a fun touchstone to me to use as, “This is the feeling of Massachusetts.” It’s not holistic, it doesn’t cover every experience, but it does evoke a kind of specific masculine energy in a way that I think is, again, not always fair. They’re politically, it seems, pretty righteous and outspoken. That song feels like you could intro a UFC fighter to it, but it doesn’t have the politics of UFC or Dana White specifically, right? They’re not going to play Trump’s inauguration.

The idea that you wear shamrock camouflage — shamouflage — when a Dropkick Murphy is born or dies…

I love saying things that are so stupid. How would you possibly know when a new Dropkick Murphy is born, because it’s like, does that mean one of them has a child? Does it mean it’s an appointed scion of the Dropkick Murphys?

Like the Dalai Lama.

Yes, exactly. Like, “Oh, this baby will be the next Dropkick Murphy, even though it bears no genetic relationship to anyone in the band.” Right. “Born or dies” is so stupid.

As someone from the ‘90s, your bit about giving turn-of-the-century electronics “technicolor BBLs” was very resonant for me.

Oh yeah.

It wasn’t just computers — they did it to George Foreman grills too. It really was a moment. 

Yeah, the cover would have that kind of teal translucent or purple translucent casing. It was such a specific aesthetic. I thought it was really cool then. I had the iMac or iBook laptop for college, and it had the blue translucent plastic and I was like, “Well, this can’t be the sturdiest material to make a computer out of that’s going to get banged around in a backpack all day.”

I wonder if it was a reaction to the Y2K panic where it’s like, “Computers are fun, they’re not scary.” 

They’re fun, they’re safe. They’re not going to launch intercontinental missiles without human consent. 

You also have a bit about an ex who transitioned their gender since you dated. What is it like to let someone know you’re going to be doing a comedy bit about them, even if they’re definitely not the butt of the joke?

That joke took a lot of delicate wording and effort in the way I put it. This is maybe the wrong way to do this generally, but my feeling is almost always, unless what I’m saying is a secret about someone in my life, unless I’m going to say something that’s like, the people around them don’t know this, even if I’m anonymizing, I do the bit a couple times to go, “Does this work enough that it justifies the hard conversation?” If it doesn’t work, no harm no foul, nobody knows. I’ve said it twice in front of a total of whatever, 50 to 300 people, and I get to go, like, “That’s all.” And it evaporates into the air. 

But this one took a little massaging. My conceit of it in my mind was, I didn’t want it to feel like there was any “no homo” in the bit. I just wanted it to feel warm, first of all — warm and generous to the person it’s about who is a public figure and who has acknowledged that the joke is about them. It’s my friend Gabe. So I really wanted to make sure the bit felt loving and warm toward my friend. 

Then I also didn’t want to sound like I was distancing myself from that. I wasn’t trying to hold queer culture or identity away from me in a way that was pushing away people that would hear it. The way the bit ended up, I feel very fair about what I said because, really it’s just like, how do I talk about my sexuality accurately and gently in light of this change that kind of happened not to me, but also one of the ripple effects of this was like, I have to think about my language carefully now. 

And so, I texted Gabe about it, and the only change that they requested was I had said I was in a “same-sex relationship,” and he was like, “Oh, I would say ‘gay relationship’ — that just feels realer to me.” And I immediately took the note and was like, “If that’s what you feel about this, however you define this facet of sexuality, that’s what I will run with.” It was a really smooth and helpful conversation, and I think they like the bit — I think they kind of claimed it, which is really nice.

There are ways to talk about people and talk about issues that are in the ether, in the news, and without that feeling of “This is new to me and I hate it and I’m going to trash it up and down” or “trash this person up and down.” I feel really good overall about the response that trans people have had to that joke. And if it was bad, even though it didn’t feel like I was saying anything mean, I would be like, “Well, I don’t want to bum people out with this, especially the people that are touched by the subject matter of the joke.”

How did you decide which sneakers to wear for the special, and can you describe the ones you picked?

Yeah, so I wore these bright orange Adidas Gazelles with a gum sole, a kind of translucent tan sole with bright blue laces, and it’s the inverse colorway of the sneakers I wore for the last special, which were Nike Dunks that were a bright sky blue with orange outsoles. I’m trying to think if that’s where I started. I know the pants and the T-shirt were last with the outfit, and the cardigan and the sneakers both have that bright orange in them. I really build from the sweater and sneakers when I’m recording something.

For the intro and in the key art, I bought the same sweater in the flipped colorway too. I had two versions of the same sweater. I try one on, and to me, it’s a silly subtle joke that I look at basically the identical sweater and I’m like, “no,” shake it off, put on the first sweater again. And then in the key art, I’m wearing that sweater, and the other one is over my shoulders, kind of preppy-style.

Are you comfortable sharing the size of your sneaker collection?

Yeah, it hovers around 50, but I’ve slowed way down since I don’t work for Desus and Mero anymore.

Your late pug Bizzy comes up in Positive Reinforcement, and you dedicate it to her memory. You and your wife Maris recently adopted a pug named Maggie. How is it going?

It’s so good. We are so happy. (Bizzy and Maggie) are, dispositionally, really different. Bizzy was always more anxious to do anything. She hated cars. She hated new places, ambivalent toward most people, very treat-motivated. Maggie loves every person, is skeptical of 50 percent of dogs. We cannot figure out what quality in other dogs sets her off. She hates seeing dogs on TV exclusively. She doesn’t ever like that. Maris made her watch Bluey to see if she recognized Bluey as a hateful dog, and Maggie immediately was like, “Yep, hate this too.” Ran right up to the TV, started barking, but is much more amenable to going places. 

We took her to see my in-laws, and we can put her in a car and take her to the park or walk her further. When we got Bizzy she was basically eight years old. Maggie is four and a half, so she’s just a little more spry and we’re getting to live her younger years with her, which is really a privilege — to have adopted but still get a young dog who’s moving around. 

Bizzy was so funny. She would jump up on the couch and sit with us. Maggie, I think she could do it. We’ve seen her do it once, get a running start and hop up onto the couch, but she prefers to be plunked, which is really funny.

Your special is out today. How will you celebrate?

I’ll be in the live chat when we premiere at 8 p.m. (EST) on the Blonde Medicine YouTube channel. I’ll probably have a nice lunch with my wife. I don’t want to do too much. Someone suggested a little karaoke outing afterwards because we will be done with a stream at like nine, and then the night is young. But also it’s the week before my wife’s new book comes out and we have so much exciting stuff planned. I don’t want to do anything that overshadows that real triumph or for her to tire herself out celebrating my stuff so that she doesn’t feel at her best when the book tour starts. 

So I don’t want to really overdo it. Maybe I’ll buy a new pair of sneakers.