DMA#54: The Kindest Cut with Josh Gondelman

I said at the top of this episode that I didn’t want to call Josh Gondelman 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 f*****g 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.