5 questions with comedian Josh Gondelman

By Reed Sedgwick

The weekend of November 18 and 19, Planet of the Tapes is excited to bring headlining comedian Josh Gondelman for two shows each night.

Gondelman’s career has spanned a wide array of media, including as head writer and an executive producer on Showtime’s “Desus & Mero,” and as an Emmy-winning writer on “Last Week Tonight with John Oliver.” You may also know him from his regular appearances on NPR’s “Wait Wait…Don’t Tell Me!,” or his many late night appearances.

Despite the traits that make Josh Gondelman’s self-deprecation hit, you might feel like you need to be more like him. He somehow radiates good will.

Following the trajectory of his career, standup-wise, the more pointed attitude of his time as a young comic in the Boston scene has softened. That’s not to say that his comedy is any less punchy, just that he seems more purely who he is, and that gives him a powerful vulnerability onstage.

Gondelman has at various times called himself “a hipster Mr. Rogers,” and “a cardigan as a person.” Those descriptions don’t capture the wild creativity he brings to his often narrative bits.

A recent track from his latest special, “People Pleaser,” about his father’s recent health scare brings whacky pop culture references, deep concern, politics, and his parents’ sex life to the fore without ever seeming to get off track. You never have an inkling of where he’s going next, just that you’re glad to be there.

Josh Gondelman on The Late Late Show with James Corden.

Gondelman took the time to answer 5 questions from Louisville Laughs.

Louisville Laughs: You seem like a capybara of comedy. If you don’t know about them, they are cute animals that other animal species often mob with snuggles. They exude some sort of cuddly magnetism. Over time, it seems like you have gotten more vulnerable on stage. Can you name any factors that changed your style?

Josh Gondelman: I didn’t know that about capybaras! All I knew is that they’re the world’s biggest rodents. It’s so funny that they also have this level of inter-species charisma! Way to go, you big weird rats!

I think a big factor in getting more vulnerable onstage is getting better at joke writing.

When I started out, I felt the limitations (as I imagine many new comics do) of my skill level. So I talked about a lot more stuff that literally happened to me and felt objectively funny on its face. But with experience, I’ve gotten more skilled turning the things I’m interested in talking about into material, which is really gratifying.

It doesn’t always work, but I have a much better chance of sticking the landing if I want to talk about … the stock market or feeling weird about aging rather than just overhearing someone saying something goofy on the street or cute stories from when I was a preschool teacher.

Josh Gondelman, photos by Mindy Tucker

Louisville Laughs: You’ve described yourself as “a cardigan as a person,” but also said you still have angry moments — in traffic, for example. What other circumstances bring out your aggressive side?

Josh Gondelman: When I watch sports (especially Celtics games) I turn into a person that my loved ones would barely recognize. The (Boston) accent comes out a little, and I get VERY hyped up. It is borderline humiliating, but also it’s a better outlet for that kind of energy than shouting at an airline employee during a flight delay.

Louisville Laughs: As an executive producer on Desus & Mero, and throughout your time as a writer on Last Week Tonight, you were still doing standup and releasing albums. What’s your process to keep on top of at least 2 creative jobs at the same time?

Josh Gondelman: I always love going out and doing sets! It’s really helpful to me to have a creative project that’s just MINE to work on. But what’s been really useful is not kicking my own ass if my standup writing slows down while I’m working on a job in the daytime. I used to wonder why my writing wasn’t keeping pace with friends who do standup full-time, and then I was like…oh! Because they work on it full-time. Duh.

In 2018, I was working at Last Week Tonight, doing standup, and writing a book. THAT was maybe too much to do all at once! When I planned things out that year I forgot to schedule things like seeing friends and sleeping and showering. Since then I’ve tried to balance things a little better.

Louisville Laughs: You’ve written not just for TV, but The New Yorker and McSweeney’s to name a couple publications. Can you speak to how your process for writing standup and writing for the page or screen are similar or distinct?

Josh Gondelman: With standup, I get to do exactly what I want, which is fun! But with other kinds of writing, it’s about figuring out how to cram my skills and taste into a format that someone else dictates.

With something like The New Yorker, there are certain kinds of jokes that are just too dumb or dirty to work, but goodness knows I try to sneak them in. And then with TV writing, it’s all about figuring out what I can bring to the table for the host or characters to say that feel unique to what I have to offer. But it still has to sound faithful to who they are, and not like I’m trying to put on a little puppet show using other people to speak in my voice.

Louisville Laughs: What is your comedy horror story?

Josh Gondelman: Oh geez. There are SO many. Maybe the worst one was a friend’s agent booked me for a week of shows in Atlantic City, and they were NOT going well.

The club owner called me Friday morning and said that he heard I was bombing every set (not quite true, but close) and that I needed to step it up. Then, before he hung up he said: “… But remember, Friday night late show is why Steve Martin quit standup, so … good luck.”

I didn’t need to worry though. I had a pretty mediocre set on the early show that night, and the club manager fired me before the late show even started. Instead of staying the night, I left immediately to drive back to New York, and in my rush to flee I lost the pants to the suit I’d brought to A.C. with me.

The whole ride back I listened to various covers of the song “Atlantic City” by Bruce Springsteen to really wallow in the bleakness of it all. But, on the plus side, I got to leave Atlantic City a day and a half early. So it’s not ALL bad.

Learn more about all of Josh Gondelman’s projects and his standup at his website and find him on Twitter and Instagram.

Catch Josh Gondelman at Planet of the Tapes on Friday and Saturday, Nov. 18 and 19 with showtimes at 8:00 and 10:30 each night. Get tickets here.

Author: Creig Ewing

Writer, comic, cubicle dweller. Louisville Laughs

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