Photo: Mindy Tucker

As a Peabody-winning and Emmy Award-nominated writer for shows like Last Week Tonight With John Oliver and Billy On The Street, Josh Gondelman is responsible for some of the funniest work out there today. A consistently sharp presence online, Gondelman also co-created the Modern Seinfeld Twitter account, a wry look at what sort of bickering Jerry and the gang would be up to in the age of texting and Twitter. And with a new record —Physical Whisper, out now on Rooftop Comedy—Gondelman is weighing in on everything from sweatpants to why his grandmother was cremated in a Tom Brady jersey.

Continuing an idea we’ve done with comedians like Mike O’Brien and Jon Glaser, The A.V. Club asked Gondelman to run down some of the stuff that consistently makes him laugh. Let it both give you a look into Gondelman’s psyche and, hopefully, show you some hilarious stuff that you might not have seen before.

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Reductress

The A.V. Club: Why did you pick Reductress?

Josh Gondelman: It’s just so funny and so on point, and it’s one of the rare comedy outlets where every time I scroll by it in my Twitter feed, I’m like yup, delightful, love it. And there was an article yesterday that was “Five Infinite Jest footnotes that will get him rock hard.” And I just laughed out loud. I thought it was so funny.

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It’s just so funny. Descriptions of the footnotes from Infinite Jest. It’s very specific. I like comedy that’s very specific and isn’t afraid to lose people through its specificity.

You know what I wish I had included but didn’t, but I’ll bring it up now? There’s a sketch on Chappelle’s Show from the third season that never aired on Comedy Central, but it was just the “Wu-Tang Torture” sketch from Enter The 36 Chambers, and it’s just him in a hospital bed describing the tortures that were performed on him by the Wu-Tang Clan. He goes through all the horrible things that they promised. “They leave my nuts out on the dresser, just my nuts.” It’s only for people that know that very specific thing. Millions of people have heard that Wu-Tang album, but it still feels like this is a special thing that I get to enjoy.

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AVC: Jen Kirkman did one of these lists for an upcoming piece, and she mentioned a bit from Caddyshack. There’s this scene where Chevy Chase hits a ball into Bill Murray’s golf shack and plays through, and they have this big conversation on the way. Apparently it was all improvised, and Bill Murray is just talking about different kinds of grass and the ways you treat grass. And that’s so funny because it’s so specific. Who knows what the different strains of grass are called, other than Kentucky Blue?

JG: Totally. It doesn’t have to be specific cultural references, but any time you get really nitty-gritty is really fun. A fictional character is always funnier with a name, for instance. At least, if you’re talking about a hypothetical character rather than a fictional character. A hypothetical person is always funnier when you name them because that evokes something in the listener or the viewer or the reader.

AVC: Recently on Comedy Bang! Bang!, Scott Aukerman said something about how you shouldn’t make a reference unless you can make a second one. Don’t just say David Hasselhoff was in Baywatch. Bring up David Charvet, too.

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JG: Oh, wow. I think that’s super right. You shouldn’t just be like, “This is like The Notebook,” unless you know one other thing.

That’s so fascinating. Hearing that for the first time, having that on the tip of my ear, I’m like “Yep. Totally.” It sounds wise, and I’m sure it holds up, but it certainly at first splash, yeah, what a great rule of thumb.

ClickHole

AVC: Sticking to websites, you have ClickHole on here. Our sister site is certainly a master of a particular specificity as well.

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JG: It’s really great. It’s so nice. The thing that made me laugh most recently was the story that was premised on the fact that Jerry Seinfeld hates being in cars and is trapped in these luxury cars driving other comedians to get coffee. It’s very funny. You have to know he has this webseries, which again is big enough that a lot of people know about it. But also, if you are more familiar with Jerry Seinfeld’s other work, as I imagine there are people who are, then if you’re like, “Why is he in cars?” It’s just so funny.

AVC: You have to have a specific sense of humor to get some of those.

JG: Definitely. And I also think ClickHole requires literacy of memes, or maybe meme construction rather than specific memes. It’s the idea of how articles are formatted for the internet. There was one that was like “You’ll never look at a Twinkie the same way again after watching this,” and it was a guy shooting another guy in the heart with a Twinkie. It doesn’t make sense unless you know that as a construct. So it’s not a cultural reference. “Oh, you don’t know that song lyric from the DMX song? You won’t get this joke.” But if you know this lexicon and this grammar of internet writing, then you will enjoy this.

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AVC: There’s a video they did called “Racists will hate this video.” Have you ever seen that one?

JG: I think I saw the headline, but I didn’t see the video.

AVC: It’s a domino rally, and then at the end, it says “mixed race couple.” That’s one that comes up a lot.

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JG: That’s so funny. And then “Which one of my garbage sons are you?” That’s the one that is the greatest hit in my experience when people talk about ClickHole. It’s just so funny, and it’s so dead-on in the same way that Reductress is. It’s dead on mimicking the language of the thing it’s parodying, and parodying in a really funny direction.

I think the Reductress article I had sent you before was like, “How to roast a chicken that will make him park his dick forever.” It’s very funny, but additionally the site’s concept is that it’s ostensibly a women’s magazine, but it’s specifically talking about boners all the time because that’s the subtext of it all—ways to drive your man crazy. All the Reductress articles are like “how to get his boner hard.” It’s just so funny to say the thing that’s always the coy subtext as blunt text. That’s always a thing that makes me laugh.

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Dan Guterman’s “New Optical Illusions” for The New Yorker

AVC: Why this piece?

JG: It comes at you from all these different angles. There are all these different kinds of jokes that are varying degrees of incredibly silly and really poignant. The optical illusions include a trident, only the trident doesn’t make any logical sense because “Who do you think you are, Poseidon?”, which is very silly and plays on the optical illusion. There’s one that’s dyslexia, which is heartbreaking, and there’s this one that’s a long description of a relationship. Again, I’m doing that thing where you talk about a joke and destroy all the fun and joy in it, but the last one ends with a description of a relationship that ends in heartbreak, and the last sentence is “This optical illusion is called Sarah.” It’s so great.

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AVC: That’s pretty specific.

JG: And every kind of joke you would want made in this or could conceive of making is made. Jokes about specific optical illusions. Jokes that are completely absurd, jokes that are sad and then jokes that come at an angle where you’re like, “Oh, I had never thought about that.” It’s really great.

It’s so dense, and each illusion is very delightful. It’s a bunch of descriptions and they’re all different, and so it’s not the same beat over and over again. And it has these emotional stakes, even though it seems like it’s going to be entirely an intellectual exercise, which I think is a neat trick to do to start off. Like, ”Here’s the premise,” and then to bring it to this deep, emotional place.

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Gary Gulman on Late Night With Seth Meyers
Nate Bargatze on The Tonight Show

AVC: Do you think you admire these types of written pieces more as a writer because you know all the work that goes into them, or more as a fan? Do you have a second level of appreciation?

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JG: Can I segue to a different thing to answer that?

I included a couple of late-night sets, specifically the Gary Gulman and Nate Bargatze, just for this purpose. I watch them as a fan. They’re comedians I enjoy and watch for pleasure, but for me the highest compliment for a bit is when I seethe with anger because of how much I love it and how good it is. That to me is the highest form of appreciation. There’s the fan level of, “This is so funny and it causes me joy.” And then there’s the writerly, “That’s so good that I resent that you, and not I, have created it.”

In the Gary Gulman late-night set, there’s a line where he’s talking about his brother chiding him for a frivolous purchase. He’s like, “Gary, it adds up. You can’t spend money like that. It adds up.” And he goes, “My philosophy is it only adds up if you add it up.” And it’s so beautiful and simple. It’s like, if there were a diamond sitting in the front door to your home on the street and you walked by it every day, and then someone showed up and picked it up and was like, “Hey, I found this diamond,” and you’re like, “That’s your diamond because I’m too enwrapped and encircled with how I see things every day in my own head to notice this wonderful, amazing thing is directly in front of me.” And not me specifically, but it’s just out there in the world for you to enjoy. But obviously that’s not what it is. It’s a great insight that Gary had.

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Nate has a very similar way of having these insights that feel like you could have had them, but you couldn’t because they’re both really exceptional at having an awareness of the world they live in. Nate’s line is about not being smart, and he’s like, “If I went back in time, I wouldn’t be able to prove I was from the future.” It’s the best most beautiful, crystalline articulation of that and it’s so whimsical. And both of those bits feel like the easiest thing in the world to have written, but that’s only because the person who wrote them has this exceptional insight about themselves or the world around them. I’m just so dazzled by that kind of clarity of expression.

Key & Peele, “Sexy Vampires”
Key & Peele, “East/West College Bowl”

AVC: I don’t write comedy or produce television, but I felt that way a bit about Key & Peele’s sexy vampire sketch, which you also had on your list.

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JG: “Why are vampires always sexy?” Also “East/West Bowl.” Both of those have the very specific thing of, this is something that maybe you’ve noticed, but we’re going to say that it’s a thing. We’re going to say, “Why are vampires always sexy? Why are they not dumpy or awkward?” They have beautiful physiques, and they wear goth orgy attire at all times.

AVC: There’s a line in there where they’re like, “If we’re going to eat, let’s eat.”

JG: Yeah, yeah, yeah. Because they’re just like licking people’s faces. It’s so funny. “I let myself get bit because I wanted to see what future cars were like.”

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The idea of a vampire that’s not into vampire culture is really great. It’s so funny, and again, it seems right there. Like every vampire you see from Blade to Twilight to Lost Boys, there’s always a dangerous edginess. There’s never a goofy lack of understanding. It’s always brooding. I guess the other exception recently was What We Do In The Shadows, which was really funny and I liked very much.

And then the “East/West College Bowl.” It’s not just the names. It’s the way of making eye contact with the camera that is so funny, and the inflection of the school spirit and saying what schools they’re from. It’s so thorough. That’s an example of the rule of, “if you’re going to make a reference, be able to make the second reference.” It’s not just that athletes have unconventional names. It’s also this trope of, “Why do we have these weird floating head things where they say their own name, and what college they went to?“ What attitude are they supposed to have about that?

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Also, whoever their wig person is deserves every award that’s ever been invented. They deserve a Nobel Prize for wigs.

AVC: The “East/West College Bowl” has really caught on for Key & Peele. That thing has 35 million views on YouTube.

JG: It’s amazing. It’s one of the few comedy things that I’ll see and send to my dad and be like, “I know you will also love this thing.” There are things that I like that I’m like, “Oh, not for him,” or things that I see that I’m like, “Oh, maybe you’ll like this, even though it’s not exactly my cup of tea,” but this is something that I laughed out loud at and then sent to my dad and was just like, “You’ll get this and you’ll like it in the same way that I do.” I think anyone who’s ever watched football on purpose for their own enjoyment will like that, and that’s a huge swath of people. And even if you’re not a football fan, there’s something to enjoy just because of the silliness and whimsy of a guy whose name is a jackhammer sound.

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Bernie Mac’s “I Ain’t Scared” set on Def Comedy Jam

JG: The Bernie Mac set is amazing. I don’t want to say it wrong, but there’s a backstory there. It’s an often-cited thing, but I’m certainly susceptible to the allure and charisma of the set. I believe the backstory is that it was an incredibly turbulent audience for this TV taping, and the guy before Bernie Mac had been booed off the stage. Anyway, Bernie Mac’s routine didn’t originally involve queuing the DJ. I must have heard this is a podcast or read it in an interview with another comedian that knew it better. But knowing that going in, it’s just his opening, cut the music, “I ain’t scared of you motherfuckers.” Audience goes crazy.

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That’s definitely something as a comedian that maybe I appreciate on a different level than just an audience member because I’m like, “Wow, that crowd would have eaten me alive.” People would have thrown knives at me. Not that that’s what the audience was doing, but I would have brought out rage in any audience that was booing people off the stage recreationally. I would have just been the exact wrong antidote. It would have been like treating an illness with a medicine that you’re allergic to. And Bernie Mac goes out into this incredibly disruptive crowd that is combative with the comedians and just immediately displays poise and confidence and authority in the face of what I would consider certain demise.

It’s just a reminder to me of the importance of showing an audience who’s boss. And showing that you know what you’re doing and you’re the one who’s in charge because that’s something I forget. If I start a set and the audience isn’t into it, I’m like, “Maybe they’re right. Maybe I’m doing the wrong job,” instead of being like, “No, I just need to sell it harder or try to find common ground or establish my expertise instead of retreating.” It’s such a display of raw unwillingness to let the audience beat him. Plus the dancing and that he’s wearing jeans with his face airbrushed on them.

AVC: He’s pre-owning all of it.

JG: I only ever remember one of the jokes from that set, and I’ve watched it a bunch of times. Bernie Mac was a great writer as well, but for this set, man, he is projecting something that’s undeniable. You watch that and you’re like, “This person’s obviously a star.” You see him, the way he’s conducting the crowd and bringing all these elements to get the music and the bold fashion choices, and you’re like, “This is great.” It’s the highest level of confidence and overpowering an audience that wants you to fail. And I think definitely it is the opposite of how I would respond, and that’s why I admire it so much.

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Shea Serrano’s The Rap Year Book

JG: The Rap Year Book is really great. Shea Serrano wrote it, and it became this huge phenomenon where he sold out everywhere and made the bestseller list just on the strength of his fans on Twitter wanting him to succeed. It was really touching and beautiful to see people being like, “Yeah, I bought five books because I’m trying to make Barnes & Noble sell out.” Or “I bought three books from my local bookstore so they have to order more, and I’m going to give them away as Christmas presents.”

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You hear all the horror stories about social media or people getting off social media because it’s not worth it, and those are all real, but it’s nice to remember this isn’t just a toilet. There’s also the potential for these really lovely genuine interactions where people can really support the work they like, and people can reach out to the people that will enjoy their work. And like artists, writers can reach out to the people directly who would enjoy their work. In a way, that’s much more personal than you could achieve through other means.

And the book is so good. It would all be a sweet story on its own, but the book is so funny. Shea’s got these descriptions of the most important rap song every year from either ’78 or ’79 to 2014 I think, and he’s such a funny writer. There are all these little personal anecdotes in there that are really funny observations. I was on vacation with my girlfriend, and we were on a Disney cruise with her whole family. So we did a lot of retreating and reading places where we wouldn’t be found by the 1,100 or however many children were on the boat, and so I read this whole book in I think a day. I kept interrupting my girlfriend to be like, “This part’s so funny.”

The DMX chapter was written with this real tenderness toward DMX. I think the whole book was written from a real place of love for rap music and for rap artists, but the chapter about DMX—it’s so easy to make fun of someone who’s had hard times, but for Shea to be really compassionate and use quotes from DMX’s autobiography, E.A.R.L. Who quotes earnestly from a rapper’s autobiography? And I mean that admiringly. That’s the right way to treat art you love and admire. It’s not to mock it when it ceases to serve you. Hilarious, laugh-out-loud funny.

Another Round with Neben Nigatu and Tracy Clayton

AVC: Can you explain what Another Round is?

JG: I love Another Round. It’s Heben Nigatu and Tracy Clayton’s podcast that’s through BuzzFeed, and they’re real funny and really themselves. And I like it because it’s very funny, but it’s outside the realm of comedians talking about comedy. So you get a whole different perspective. You get humor coming from people who aren’t necessarily like, “Yes, I go up at these comedy clubs and I tour these comedy rooms and I write for these comedy outlets,” and it’s nice for humor to come from a different perspective. It’s very joyful, but also very smartly analytical about things.

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I thought their interview with Hillary Clinton was really incisive in terms of asking hard questions, but also Hillary Clinton was charming in the way that I don’t think she’s often given a chance to be. I think she’s expected to be so straitlaced about everything that it was nice to hear her both answer hard questions, but also to get to be a person in an “Oh, you can be funny and then say something serious in the next breath” way. It doesn’t have to be all sorted out. You don’t have to go, “Here’s when I’m being funny and here’s when I’m being serious.” It’s nice to hear a candidate as a whole person, when she’s so often stereotyped as being robotic and cold.

AVC: It’s like when Obama was on WTF. He was just a guy having a chat.

JG: Totally. But I think he’s had these opportunities as a president where you get a little more liberty to be charming. You see him sing and crack jokes, and he has very good timing. Given Hillary Clinton’s career, she hasn’t had a lot of opportunities to put that on display with the same kind of safety net of, “I am the elected president, and it is my prerogative to make a joke.” And so it was good. Whatever you think about Hillary Clinton, I thought it was a fascinating interview and multifaceted, and I like that.

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They have people you don’t hear on every podcast. Vann Newkirk was on a couple of weeks ago, and he was one of the founders of Seven Scribes. Lin-Manuel Miranda was on this week. It’s just cool people that I haven’t heard on every podcast, and Tracy and Heben are super funny and great.

AVC: Do you know them personally, or do you just like the show?

JG: I do. I knew Heben before. We were friends before they had the podcast. I’ve met Tracy since, but I knew her from Twitter as well.

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AVC: Twitter has really brought a lot of people together.

JG: I think so. I’m a big fan of the medium. Again, I don’t want to discount that there are really gross things that happen across social media, but I will also say I think there are also really nice things. I’ve learned about a lot of great culture and great people that I wouldn’t have otherwise known.

@GMPaiella

My favorite sex position is when I lie down next to my boyfriend and read him all my best tweets

— Gabriella Paiella (@GMPaiella) December 3, 2015

AVC: Speaking of Twitter, Gabriella Paiella.

JG: Gabby is someone I know in person, and she’s super funny. Her Twitter is a bunch of running bits, but the funniest running bit that kills me every time is the great gravity with which she talks about being a model/DJ, which she is not. She’s a writer. She’s so funny and just delights me to no end, but she’s also for sure the person I retweet the most. Several times a week, I’ll just be like, “This is really good.” And she’s definitely the Twitter account that I most frequently will be scrolling through my phone, and then just bother my girlfriend like, “Look at what Gabby said.”

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The model/DJ thing is so consistently funny. “As a model/DJ, the hardest part is” etc. etc. I don’t know exactly why it kills me.

I just retweeted something of hers that said something like, “I’m going to Boston tomorrow for the first time since I moved, and I’m expecting every Dropkick Murphy to be waiting for me at the bus station,” which automatically I will retweet because Dropkick Murphys-related jokes are maybe my favorite microgenre of humor. I think the last two years, I’ve spent all of St. Patrick’s Day live-tweeting a fake Dropkick Murphys itinerary. One year, it was about them trying to play a surprise show in every town in Massachusetts that ends with -ham. Needham, Stoneham, Deadham, Wareham. Just dumb stuff like that.

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The previous one that I had retweeted from her was like, “It’s me, Neil DeGrasse Tyson. Your childhood dog didn’t go live on a farm, and your parents, partner, and children don’t love you at all.” It’s just super, super funny. And massively underfollowed, which is a backhanded compliment already. Just to call something underrated is to compliment it, and also be like, “It’s not popular or not popular enough” certainly is.

“You know that metal thing waiters at fancy restaurants use to scrape off the table? That’s the main way I use my Apple remote.” Just very funny.

AVC: It’s a skill to be good at Twitter. There are very funny people who aren’t necessarily Twitter-funny people.

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JG: There are very funny people who aren’t good at Twitter and people who are really good on Twitter where that’s the best or the only thing they do. There are some people I know that don’t write creatively outside of Twitter, but they’re so good at Twitter.

AVC: It’s been a weird boom, especially with Weird Twitter. A lot of those guys are just tech nerds or random dudes that just happen to be good at Twitter.

JG: It’s very interesting, and it’s its own vocabulary. I’m on Twitter a lot, and I don’t even get that stuff necessarily all the time. Something will bubble up and will be funny and very weird but resonates with my sense of humor, and then sometimes I’m like, “I don’t know what that is.”

AVC: My husband and my brother are all into Weird Twitter and will send each other texts of tweets and joke around. And then I’ll be like, “What’s so funny?” And they’ll read it to me, and I’m like, “That’s kind of funny?”

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JG: Totally, and you then look at it, and it’s like 11,000 retweets. It’s like, how? Who? But then I guess it’s that version of the Wu-Tang sketch, where I guess I can see what’s interesting about it, but the enjoyment of it has not saturated for me.

AVC: It’s great that everyone has their own little niche now. You can find the Twitter account that’s for you. You can see something and think, “Oh my God, how do they know me?”

JG: That’s maybe the best thing about people that write on the internet. It’s not like television, where you have to convince someone that a certain amount of people will understand it for it to be out in the world. You can be like, “Here’s a joke that I like, and maybe other people will.” And then it’s there, and then people can find it, and I think that’s really exciting.

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Bob’s Burgers

AVC: Speaking of TV writing, you have Bob’s Burgers on your list. That’s a popular show.

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JG: It’s so fun. If I’m talking about specific things that make me laugh, the text in the background on Bob’s Burgers is exceptional in its own right. There’s one—I believe it’s text. I hope I’m not wrong about this—but my favorite episode is the one where there’s a biker gang and their leader had died in a biker accident and his name was Horny Dave. And there was one line where someone was mourning him, and they were talking about the bike accident. They’re like, “That tractor trailer came through and took the lower half of him. The lower half, clean off,” which was very funny. But at the funeral, there was a big banner, and it said something that, if I was looking at my phone instead of just listening to the TV, I would have missed it. But it was a banner in the background at the funeral that was like one you would put up at any kind of party in a hall to make it look like what it is, and it said “Horny Dave. God gave him a halo because he wouldn’t wear a helmet.” It’s just such a dark joke, but so silly at the same time.

All the burgers of the day and the different exterminator trucks that drive up in the credits, those are an extension of the voice of the show being so well defined that everything every character says is a joke pretty much. It’s overflowing with jokes. There are so many jokes that they’re just being written on the screen.

AVC: The Simpsons was always good about that too—the names of stores and things in the background of shots. People don’t appreciate it quite as much anymore.

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JG: Totally. Everything that could be was a joke. Even when it doesn’t matter to the story, but they had an extra eight seconds where they could squeeze in a joke of walking out of a cookware store called Stoner’s Pot Palace. I think the line was, “That’s flagrant false advertising.” That level of, “This could be just the next joke. We could wait until we get to the next setup to punch in a line, or we could add another joke before there is even a setup for it,” and that’s so delightful for it to be so dense and fun.

AVC: I don’t even know how you do that with animation. On a live action show, you put a prop in the back. With animation, I suppose you have to write it into the script.

JG: But there’s also unlimited stuff you can do too. Something can fly by, like a shoe that would never fly. A shoe with wings, of course.

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It’s like Rick And Morty, which is on my extended list. That show’s really good at that too, just having interesting visual things on screen all the time.

AVC: Are there things on this list that you think have specifically influenced you? Are there things on here where you can say, “I’ve watched this and came in really fired up to work the next day or wrote something for myself”?

JG: The specific stand-up stuff has definitely been influential in very specific ways of how you can say things that clearly or you can be this way on stage. You can own the stage in such a way. A lot of it is aspirational in terms of, “This is the standard. This is how it can be done.”

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It’s the same thing with that New Yorker piece. If I can’t do it that well or if I’m not striving to do it that well, something in that genre, then I’m not setting my sights high enough. And if I can’t achieve that, then maybe I do as well as I can, but you can’t come in coasting. I try to bring myself up to that level where everything I do I’m working toward being that good.

The Rap Year Book, too. Shea wrote a book that was exactly what he wanted to say, and there was a point to everything, but also there were jokes on jokes on jokes, and it was visually great, so that’s what’s possible. I couldn’t write a book that doesn’t aspire to that level of innovation and density and joy and meat. He really is talking about stuff and bringing things to the table, but it’s also constantly great jokes. So if I’m not aspiring to that, I’m shooting for a B at best, and I feel like my comedy ethos is to shoot as high as I can. Maybe I’m only B+ capable at certain things, but hopefully I continue to improve.