I said at the top of this episode that I didn’t want to call a comedian, because the word does about a third of the required work.

Here is the CV, and I have since checked it against his actual bio rather than my memory, which is a courtesy I extend to guests and to no one else. Five years at Last Week Tonight with John Oliver, first as web producer and then as staff writer, where he collected four Emmy Awards, two Peabody Awards and three WGA Awards. Head writer and executive producer on Desus & Mero at Showtime. A contributor to the final season of The Marvelous Mrs. Maisel. Two stand-up specials: People Pleaser (2022) and Positive Reinforcement (2025). A book of essays, Nice Try: Stories of Best Intentions and Mixed Results. Co-creator of the parody Twitter account @SeinfeldToday. A regular panellist on NPR’s Wait Wait... Don’t Tell Me!

We first met about ten years ago at Union Hall, doing Picture This, the show where cartoonists draw live while comedians perform and everyone pretends this is a normal way to spend an evening. I have two deeply unemployable skills: cartoonist and comedian. My parents are thrilled. Picture This is the only place on earth where both of them are load-bearing at once.

Josh’s read on it was better than mine:

“You’re watching something that’s never happened before and will never happen again. Everybody is kind of on edge seeing how the artists will interpret the comedy and how the comedians will react to the art. It’s perfect.”

We also remembered a show where the comic on stage was working a long stretch about diarrhoea, and I, being a professional, had no choice but to render it. Gratuitously. Backstage was a convivial disgrace. We were crying.

That’s the whole show, really. Backstage is better than the stage. (Don’t tell the box office.)

The Overnight Success That Took 9 Years

I confessed that I had followed @SeinfeldToday for years without ever once registering that Josh was behind it. He co-created it with Jack Moore in late 2012: log lines for Seinfeld episodes, were they to exist in the present day, and present day was 2012 into 2013… which is now a period piece.

The numbers are fucking absurd:

“By, I would say, 48 hours later, it had like 100,000 followers... Never had anything like that happen to me before or since. It was like as close as I had to being Hawk Tuah.”

The Sunday night the account was formed, Josh had dinner with a friend who worked as a manager. She told him, gently, that she loved working with him and would keep helping him out, but that her boss was after clients with a slightly higher profile.

Two days later, the boss wanted a meeting. And to sign him!

“I’ve never seen something turn on a dime like that in my life before.”

He had samples. He’d been doing stand-up for years. But he didn’t have the bulletproof script sitting in a drawer waiting for the world to finally notice him. He had drafts that were “all kind of a little rough.” So the lightning struck, and he spent the next year converting it into late-night writing applications, one at a time, like a man turning a lottery win into a mortgage.

The heat arrives whether or not you’re ready. It doesn’t wait while you tidy up.

The Taste of a 57-Year-Old Father of Three

Nice Try is a collection of essays, and I have described it, to Josh’s face and now to you, as being like “A Kind David Sedaris.” He took the compliment the way he takes everything, which is to say he immediately turned it into an admission of ongoing inadequacy:

“We moved into a new apartment last week and I was just shelving my books and I saw my old copies of Naked... I haven’t looked at it in years, but it was like, I’m chasing that still as a prose writer.”

Same. The personal essay has a king, and we are both loitering outside the palace.

There’s a bit in the book about a childhood library trip and discovering R.L. Stine, and a line about having the taste of a 57-year-old father of three.

“Books were kind of the place where I could have more adult taste. My parents were a little more protective with movies and TV and even violent video games. But with books, it was kind of whatever I could get my hands on.”

Which is how a child ends up with real, considered positions on prime John Grisham. The Rainmaker. The Client. The Firm. He said “prime Grisham” the way other men say “prime Coltrane.” That truly is 57-year-old-father-of-three behaviour.

Writing in Someone Else’s Mouth

Here’s the thing about Josh’s writing that I’ve never been able to get past. Him on stage is him on the page. The voice is identical, and it’s completely unique, and yet he spent five years writing in an acerbic British one, and got four Emmys for it.

How?

Below: how you make an atrocity funny without becoming a ghoul, the word Gary Gulman put in my head that I can’t get out, the pumpkin quiche incident, and why the meanest guy in the room in 2007 was never the one to copy.

“In a good writer’s room, the best writer’s rooms, I think, have real diversity of perspective. And so even when the host is filtering it through how they think and talk and see things, you are bringing what your interests and ideas are when you can get it through the lens of what they do.”

Part of what the host wants, he said, is breadth. He pointed to a Last Week Tonight piece made after his time there, on Black hair care and health, led by Ali Barthwell:

“That’s really cool that John has the range to go, I’m going to figure out how to talk about this thing that is compelling to me even though it is not of my personal experience. And then I want someone like Ali who can go, I can speak to this from personal experience and I can make it sound right coming out of John.”

So it isn’t impressionism. It’s not doing the accent in your head. You learn the show’s keystone phrases and structures and referential touchstones, and then:

“How can I expand this palette in directions, like in vectors, that are fun and specific to me as well?”

Which means that all those weird esoteric tangents, the ones that feel like they’ve been beamed in from a stranger’s dream? Those are somebody’s fingerprints, and if you know the room, you can dust for them.

“Oh, this is about an angry penguin with a whimsical name. And you’re like, well, that’s a Jill Twiss specialty for sure.”

He also recalled an extremely elaborate bit, requiring numerous graphic mock-ups, concerning an ornate sex party at Wes Anderson’s house. Unmistakably Will Tracy, who went on to write The Menu and Bugonia and worked on Succession for its entire run.

Now that I think about it, I’d always been able to spot Asher Perlman on Colbert the same way. There’s a full stop that arrives, and you go: ah. There he is.

Getting Your Fingernails Underneath

I asked him the question I actually wanted answered. At Last Week Tonight, he had to take genuinely bleak news and other material and make it funny. Not funny instead of serious. Funny as the delivery mechanism for serious.

“I think that layer kind of lets you take a couple of harder swings.”

You don’t always mock the tragedy. You mock the discourse around the tragedy. But, he said, it doesn’t always have to be removed levels of commentary. Sometimes the material walks right up and hands you itself:

“Then you see the CEO of the company that did the polluting going, look, you gotta dump sludge somewhere. And you’re like, okay, that we can make fun of. We can make fun of this asshole.”

Then the second part, which is the best description of comedy writing I’ve heard in a long time:

“Look for the little things where you can get your fingernails underneath and go, oh, I can claw something up here that’s fun and funny, and not just a wry good point.”

Because a very good point that only elicits ‘clapter’ is, as he put it, its own thing. Fine. Applause is not laughter and laughter is not agreement.

“There’s an idea that you can really sink into someone’s subconscious, that they walk away and they’re actually thinking about it going, holy shit.”
…
“The efforts of these shows are not mostly to change the world. It’s to make things intelligible.”

Not to fix it. To give you the vocabulary and the narrative at your fingertips for a thing you’d half-heard and had a feeling about and couldn’t articulate. Give them the utility. Give them the words.

It’s the same job as a political cartoon, incidentally. You are not passing legislation. You are handing someone a shape for the thing they already felt.

Oliphant knew that. He never wrote for the awards. He wrote for himself, and the rest of us borrowed the shape.

It’s Pronounced ‘Quiche’

Which brings us to the vocabulary people.

Gary Gulman is, to my mind and Josh’s, a master linguist operating under cover of stand-up, and the thing Josh loves about him is the exact opposite of what you’d expect from a man with a large vocabulary:

“He didn’t invent a new word. He did not put words together in a way they’d never been put together before. But he just cut through. Just the emphasis and specificity and structure of, I’m going to use the same words twice in the opposite order. And it gets a huge laugh. To me, that’s like watching surgery.”

I told him I’d watched Grandiloquent thinking the same thing: this is neurosurgery. Fastidious to the point of being slightly frightening. It is not about being baroque or ornate with the construction. It’s the opposite. It’s distillation.

Gary taught me a word recently that I cannot shake. He and Myq Kaplan were doing their thing over lunch, the two of them together, and Gary described the practice of shepherding your sentences. He’d picked it up as a legal term. It means carefully guiding, organising, and directing the flow of your writing so it leads the reader exactly where you want them to go.

And here is where I should tell you that these are the same men who, at lunch on the Upper East Side, destroyed me. I ordered the pumpkin quiche at a vegan place. It arrived within about five minutes, which is barely enough time to make eye contact with a waiter, let alone a quiche.

“Whoa,” I said. “That was quick.”
Within half a split second, without looking up, Kaplan said: “It’s pronounced quiche.”

Gary said, " Wow! " in the tone of a man witnessing a hole-in-one, “Kaplan. That mind. He’s so…” and I said, “…Quiche?” Then it was just three idiots laughing at themselves over a vegan tart.

That’s it. That’s the whole reward. Decades of craft, a Peabody or four between us, an entire language at our disposal, and the peak human experience remains three men in their forties and fifties giggling at a homophone.

“The Born to Run of That Thing”

Josh’s stated ambition, which I’d like framed:

“I always joke that I want everything to be the Born to Run of that thing. Just give me all the horns and the bells. Give me all the shit.”

But then, the caveat that makes it actually true:

“That kind of maximalism of intention, if not of execution, I think is really beautiful. I just want to fill this vessel, whatever it is, whether it’s a book or a song or a painting, with meaning. Whether that means it’s one long brushstroke of varying pressure that communicates it really clearly, or whether it’s a novel that’s 120,000 words. As long as it is the fully realised version of the thing it is, and done with enthusiasm, I love it.”

One brushstroke of varying pressure. He said that to a man holding a pencil, live, on camera, and I don’t think he even knew he’d done it.

“The Attell of It All”

“I think maybe the most copied comedian of all time, or of the last 25 years, is Dave Attell.”

I agree, and I have receipts, because I spent years on the comics’ bench at the Cellar watching him close out the late show, trying to reverse-engineer it. How the fuck is he doing this?? It felt like a magic trick performed in a room full of magicians.

And the second you try to imitate it, you lose something in translation, because there’s a layer underneath that isn’t transferable. There’s no way to do it without simply being Dave Attell.

Josh:

“I’ve heard dozens, if not hundreds, of people where you can draw a straight line from Dave Attell to where they are. But no one that captures...”

The globe joke. I travel so much for stand-up. I used to be afraid to travel, because when I was a kid, my father beat me with a globe. One of my all-time favourites, and one of his.

“I’ve seen so many people change the setup and the punchline by one word. And it’s like, that’s not slick. We know the seed that that’s coming from is so clear.”

The inimitable thing about Attell isn’t the darkness. Josh nailed it:

“The more bleak the comedy gets, the more grimy, having that gentle touch goes so far. This is a person, there’s a sweetness in this person, and they are also willing to look at the grimy parts.”

Which is, incidentally, precisely what makes Aaron Chen work. His special Funny Garden is on Netflix, and it is one of the most singular things you’ll see. So innocent on the surface, and then he picks up a vase to drink from, and takes you somewhere genuinely deep, and you don’t notice you’ve gone.

Josh made a related point about voices being unforgeable. Maria Bamford. Daniel Simonsen, with a thick Norwegian accent that is not, on inspection, Norwegian, or anything else. No one talks like that. Whatever that is, is him.

The Kindest Cut

Here’s what I actually wanted to ask him, and I saved it for last because I wasn’t sure how it would land.

I started in Perth in 2007. Everyone in that scene was watching the same two people: Dane Cook and Louis C.K. Fellow suburban Bostonians, as it happens. And there was a meanness in the water. The comedy rewarded the fastest, meanest person in the room. That was the metric. That was the whole ladder.

Josh started in Boston in 2004, at the actual epicentre, and built an entire career being conspicuously the opposite. I asked whether it was a bit he couldn’t get out of, or genuinely his personality.

“Yeah, that’s exactly what it was. It took me a little extra effort. I started in Boston in 2004, and there were maybe a dozen guys who were like, oh, Dane Cook is what comedy is. And we’re all doing iterations of that.”

A dozen. All of them. Vituperative by default, because that was what winning looked like.

What saved him wasn’t a principle; it was proximity. He got lucky enough to be around the emerging Boston lot: Gary Gulman coming back through on Last Comic Standing. Erin Judge. Lamont Price. Joe List. The Walsh brothers, Chris and Dave, running a weekly show of strange sketch and storytelling that had no business working.

“Seeing that was like, oh, you don’t just have to do the thing that you see most prevalently or most successfully.”

That’s it. That’s the whole thing.

I sat on that bench at the Cellar for years trying to work out how to become Dave Attell, and the answer, which took me an embarrassingly long time to arrive at, was that there wasn’t one. Not because I lacked the technique. Because the vacancy was already filled. By Dave.

Josh worked that out in 2004, in a room full of a dozen men doing iterations of the same guy, and quietly went and did the other thing.

Four Emmys. Two Peabodys. Three WGAs.

Nice try.

Watch the replay, then go subscribe to Josh!

Josh writes That’s Marvelous!, a weekly newsletter of pep talks: for readers, for strangers, and for inanimate objects. He described it in the chat, and I’m describing it here because I’d like you to actually go.

thatsmarvelousnewsletter.com

Also: Positive Reinforcement, his new special. People Pleaser, his first. Nice Try, his essay collection. Wait Wait... Don’t Tell Me!, where he has also guest-hosted. All of it good. All of it kind. None of it soft.

I could have talked to him for hours and was only stopped by the tyranny of the clock and the fact that I was, by then, drawing him.

‘til next time!
Your pal,

PS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads.

DMA#54: The Kindest Cut with Josh Gondelman