Premium cable isn’t just good for boxing and sexually explicit shows about dragons. (And actually, RIP HBO boxing—my dad would be canceling his subscription if it wasn’t for Sopranos reruns.) HBO and Showtime have the two best late-night shows on TV today, Last Week Tonight with John Oliver and Desus & Mero, and as different as those two shows might seem, they have one important thing in common: the comedian and writer Josh Gondelman.
Gondelman joined Last Week Tonight from the start as its web producer before shifting to the writing staff in its second season. After five years and a couple of Emmys he jumped to Desus and Mero’s new Showtime show in 2019, where he got to add the word “senior” before that staff writer tag. Between those two shows Gondelman has helped write some of the smartest and most insightful political comedy in recent memory, while working with hosts with very different styles and sensibilities.
Throughout it all Gondelman has also been actively performing stand-up. He has a couple of stand-up albums under his belt, with a new one coming out this week. Dancing on a Weeknight will be out on April 19 through the label Blonde Medicine, and you can order it on vinyl here. You can also check out an exclusive preview of the record in the video below. In “A Gentle and Cowardly People” Gondelman talks about the abject weirdness of our current times, from celebrity presidents to Trump’s terrible ideas. Listen to it here and then read a short interview with Gondelman below, where we talk about his new album and his experiences on Last Week Tonight and Desus & Mero.
Paste: After years at Last Week Tonight you’ve moved on to Desus & Mero. How does that writer’s room and that writing process compare to your previous show?
Josh Gondelman: Truly, I’ve gone from one dream job to another dream job. It’s super different in terms of what my responsibilities are regarding what kinds of segments I’m scripting and what my media diet is in preparation for the show. I do a lot less watching Frontline episodes and gently weeping in my office at the new job. And I read much more Bossip professionally now. But the constants are I’ve gotten to work as a small part of two really excellent teams to make shows I’m really proud to be involved with!
Paste: How draining is it to do political comedy today? And if it’s not, how are you able to manage that? Because just being alive today is so exhausting—I can’t imagine also having to find ways to make jokes about everything that’s happening.
Gondelman: Of all the problems that have arisen in recent years, “Exhausted Topical Comedy Writers” are the absolute lowest priority, but it is definitely a grind to have to focus on creating comedy out of the current political climate week after week. Part of it is just how bad things are, not that they were perfect pre-Trump. But also, there was this myth that Trump was going to be good for comedy, and that idea by and large has not held up. Oh wow, he said “Tim Apple” instead of Tim Cook. I mean, of course he did. He’s an idiot. It’s hard to come up with novel observations about him, especially when those kind of slips of senility are so much less important than his racist policies and disregard for anyone but the super wealthy. Again, not that anyone should cry tears for writers working on topical comedy shows, but it’s certainly not the piñata of laughs that some people suggested it would be.
There’s lots of really interesting and good political comedy being made for sure, but in my stand-up I try not to do too much unless I have what feels like a personal observation. At least a bit I won’t get depressed or numb saying night after night. I have a few of those on the album that I like! Also though, everything is political, and I try to represent the way I see the world in bits about like…wedding rings and walking my dog. I think it’s possible to make politically relevant comedy that’s not tied to the Trump administration.
Paste: I haven’t been able to see you live yet. What kind of physicality are we missing out on when we listen to a Josh Gondelman album?
Gondelman: Ha! I’m pretty sedentary onstage, although I do tend to talk with my hands a little! The big thing about seeing me live, though, is what’s better about going to any comedy show in person. There’s an intimacy and a community experience that’s added by enjoying a show around other people. It’s like seeing a horror movie in theaters. It’s more exciting when you feel the tension and release in a group. I love listening to albums and watching specials, but there’s a reason you rarely laugh as hard as the audience you’re seeing on tv or hearing in your headphones. Especially because with jokes, you can’t turn a comedy album up in the car, roll the windows down, and shout along like with a song. You kind of need to be in the room to get the absolute best experience.
Paste: What do you prefer: stand-up, or writing for TV? And how do those processes—both your thought process and your work process—differ?
Gondelman: I like both very much, and I’m incredibly fortunate to have a life where I can do both in a nicely balanced way! I love getting to be a part of a bigger team to make something, and also having things I can do that are totally self-directed. My thought process at work has to be filtered through the lens of: “What will Desus and Mero think is funny and want to talk about?” Fortunately, we have a lot of similar interests! In stand-up, there’s the opposite problem of trying to convince audiences that my weirdest thoughts and opinions are worth listening to. They’re two really different challenges, and I think working on both kinds of comedy is really helpful to my writing in general. Plus, having a job makes the stuff I do on my own feel less stable, and doing stand-up and outside writing lets me have outlets to just say whatever goofy thing I want without having to pitch it and get it approved.
Watch Gondelman perform at the Paste Studio in 2017:
Dancing on a Weeknight will be available on April 19 through Blonde Medicine.
Garrett Martin edits Paste’s comedy and games sections. He’s on Twitter @grmartin.