DMA#54 with Josh Gondelman: Tues @ 12:30pm:

How to be funny without being a monster about it.

I’ve booked a bunch of comedians on Draw Me Anything.

Most of them arrive with a chip on their shoulder, a grudge against an open mic host in 2011, or a haunted look that says I haven’t slept since bombing at my Cellar audition. Josh Gondelman arrives with the aura of a man who once returned a wallet he found on the subway and then felt guilty for expecting thanks.

Tomorrow week he’s my guest, and I could not be more pleased about it.

Photo by the incredible Mindy Tucker

Here’s the CV, and it’s a silly one….

Josh spent five years at Last Week Tonight with John Oliver, where he collected four Emmys, two Peabodys, and three WGA Awards, which is more hardware than most people accumulate in a lifetime of trying. He then became head writer and executive producer of Desus & Mero. He wrote for the final season of The Marvelous Mrs. Maisel, a thrill he has confirmed was shared by his parents. He has two standup specials, People Pleaser and the brand-new Positive Reinforcement, the titles of which tell you roughly everything about the man.

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You’ve heard him on Wait Wait… Don’t Tell Me. You’ve possibly read Nice Try, his essay collection. And if you were online during a certain golden-rot era of Twitter, you knew him as the co-creator of Modern Seinfeld, an account that imagined what Jerry and the gang would do about texting, which was funnier than it had any right to be.

He also runs a newsletter here on Substack (and elsewhere) called That’s Marvelous!, which sends out weekly pep talks for “readers, strangers, and inanimate objects.” I want you to sit with that last category for a moment. This is a man kind enough to encourage furniture.

I first met Josh doing the show I co-produce at Union Hall called Picture This! - I was drawing for him about 11 years ago when we were both shiny baby boys… I burst into tears laughing mid-set and couldn’t control my drawing hand. He’s pretty fantastic at that.

Which brings me to the reason I actually wanted him on the show.

Comedy, as an industry, mostly rewards the sharpened blade. The quickest, the cruellest, the one who gets there first. Josh has built an entire career on the radical proposition that you can be devastatingly funny and also, somehow, a genuinely decent human being. In a business full of people performing kindness, he appears to have simply gone ahead and been kind, which is far more subversive and much harder to fake.

So tomorrow, I’ll hand him the microphone and the metaphorical pen, and we’ll talk about writing jokes for other people’s mouths, surviving five years of turning the week’s horrors into television, and whether niceness is a strategy or just a personality defect he’s learned to monetise.

Bring your questions. Bring your drawings. Bring the wallet you’ve been meaning to return.

‘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.