Tiptoeing the Writing Career Line with Josh Gondelman

Chad White

If you looked at Josh Gondelman’s resume up to this point, you’d see a pretty accomplished writer. Not only has he written for TV shows like Billy on the Street and Last Week Tonight but he’s also been able to tackle books and article writing. He even has a decent following on Twitter – not to mention the remarkably popular Modern Seinfeld account of which he plays a vital role. But where Gondelman really stands out is standup. He’s been able to hone his talents in New York, effectively turning the act into a career, which ultimately opened up a path and allowed him to take on big stages like the Rooftop Comedy Festival in Aspen, Colorado and SF Sketchfest.

Gondelman is releasing a new standup album called Physical Whisper that is sure to make audiences drown from their tears in laughter. I recently had the chance to talk to the Peabody awarded, Emmy nominated writer about his career and how he crafted the album.

Your album is called Physical Whisper. Where did the title come from?

It’s from a line inside a joke that I ad-libbed pretty close to the date of the recording. It might’ve even been the night before the recording. It was just a tiny little tag to a joke and I liked the vibe of it. It’s kind of like preposterously gentle and I think that’s a funny vibe. I kind of immediately conjured the concept for the album art in my mind of a very smooth jazz, easy listening crooner album from the late eighties, early nineties.

I could definitely see that. The soft lighting and finger over your mouth is the perfect theme and tone.

Thank you! The color pallet and layout were kind of stolen directly from Michael Bolton’s Soul Provider album. I just Googled [it]. I’m not a super visual thinker but I Googled a bunch of those artists that made that kind of music during that era and I was like “Yep, that’s it!” When I came across the Michael Bolton one I was like “That is the aesthetic, precisely, that I wanted.”

How long did it take you to write material for this and shop it around?

The material took…I guess it was about four years. I guess nowadays that’s a long time for working up a working hour for a comic but I do so much other writing. I have a writing day time job. I think, also, I don’t generate as much standup material as the people who are super prolific masters. I feel four years, in some ways, is a long time. “What was I doing? Was I screwing around?” But then a lot other ways it’s like “That’s how long the process takes for me and I’m really proud of it and I’m happy to show it off.”

Your website has dates for L.A., Brooklyn and New York. And you also appeared at festivals like Eugene Mirman’s, Bridgetown and Sketchfest. Are you still working that material along with new material inside of those appearances?

Definitely. I recorded in December. I haven’t had the time to work up enough new material to tour on that now. I’m kind of introducing old material slowly. I do have the benefit of not being a very famous person. So, when people see me live, chances are they might not have heard [it]. I mean they definitely haven’t heard the album yet, because it’s not out, but I’m going to Cleveland over the summer for a week and chances are people in the audience wont have heard the whole album yet. Which is a definite benefit to not being a household name. I can get away with doing that material and working my new stuff in slowly and still being able to go “Hey, here’s that new album you just heard – if you like it.” And not coming into a situation where everyone is like “Yeah, we saw your special dude. Where’s the new stuff?”

Coming off of your book that came out in 2015 and then Modern Seinfeld, writing for Last Week Tonight and then this album, how are you able to balance all those different types of writing?

It feels like different gears in my head. I am at my day job during the day and I love it and it’s great. I write for that. The book, I had hard deadlines that I had to hit, with my writing partner Joe Berkowitz, who is wonderful and super on point with everything. I respond really well to deadlines. Standup is kind of the writing that kind of gets squeezed into the margins sometimes. Which is why it was four and a half years between the first album coming out and the second album coming out. I try to cut myself a little slack in terms of the speed of standup writing. And also, when I have time, it is a real pleasure to write standup. Usually, when I have a week off from work, I will have the daytime to go “Oh man, I’ve been thinking about this thing a lot. I’m going to shape it into a bit.” I’m trying to get better and not excusing that like “Man, I’m out at this club and I’m seeing my friends do new stuff and I’m disappointed that I don’t have anything new.” The process is going to have to be what it’s going to be because I’m very dedicated to my job that I’m at.

I see that you’ve written for places like Esquire and New York Magazine. How did you go from internet writing these Twitter writings to writing this huge album, a book and help writing a TV show?

The internet stuff was freelance while I was writing standup. So I was doing a lot more standup writing while I was doing more freelance writing. I think it just kind of builds. I worked on it and I worked on it and I was refining myself as a writer and getting better at writing humor and writing comedy in all different mediums. I think when I ended up being able to get into the conversation for applying for TV writing jobs, the internet writing stuff was really helpful because I’d written quick topical things, which is what applications for late night shows are. It’s “Here’s two days. Turn this around and show us you can write about what’s happening now and generate new material all the time.” So the internet thing I did was a training ground for being able to do the stuff I’m doing now.

Are you given segments for the show or are you able to pitch ideas?

It’s both. It’s definitely a mixture.

Do you prefer writing your own material or do you like writing for somebody else? Is that easy for you?

I like both a lot. When I’m writing at work, I’m not jealous that I’m not writing for myself. When I have the chance to write for myself, I’m grateful for the time to do that. It’s definitely a best of both worlds situation.

Do you have any limits that you would stop yourself at writing for yourself or for the TV show? You guys have taken on specific products, people, sometimes ideas. Is there anything that you guys would stop short at?

I don’t know. I haven’t found [anything]. There are definitely things that are more likely and less likely to appear on the show but that’s to the taste of my bosses. I’m here to write the things and pitch the things I’m interested in that they’re also interested in. I haven’t had any moments of wanting to work on something and them being like “No. This is too far.” I feel that way a lot about standup too. Usually, if something is that interesting to me, I will at least try it on stage. And maybe it doesn’t work. But it’s not usually a process of censoring myself. My one real boundary in standup is to try not to say things online that will hurt people’s feelings in my life.

That’s a good thing to have. A lot of people should learn from that. There’s a lot of people that just tweet whatever’s on their mind and it just hurts a lot of people.

Yeah!. I’ve never been like “You’re going to see my truths at any cost.” What’s the cost? Oh that’s too much cost.

[laughs] Do you prefer the all hands in approach to TV writing or are you really used to writing for an audience for yourself?

Again, I like both. I like time to tinker with things in private but I also value and enjoy getting to be in a room with other writers and hearing their takes on stuff. I think sometimes, for me, if I’m by myself too much writing, I will get locked into a groove writing a certain kind of thing. And so, in the writer’s room, when someone writes a different kind of joke, I go “Oh right. That’s also possible and I should open up my own thought process.”

What kind of trajectory would you prefer to have after this album and also with the credits that you’ve amassed over the last few years?

I love the job and I would love to stay here for a long time. On the side, I think what I’m hoping for from the album and the standup is, while I continue to, hopefully, improve as a standup and write more material and write, ideally, better material, I hoping to get to bring that to bigger audiences, have more consistent, quality work when I’m not at my job, and to have the projects I work on in the future be the things I’m excited about. In the past, with some of the online stuff, it was like “Hey would you write about this thing?” And I would go “Yeah okay sure.” But I’d like to be able to keep up with that kind of stuff, when I have time, but be the stuff I’m excited and passionate about

Would you ever want to get into different forms of comedy? Say improv or sketch?

I’ve done improv and I think it was a weeding out when I moved to New York. [I felt like] I had to go so hard at standup I didn’t       end up – I just kind of let improv drop, which is totally fine. I was never great at it. It was a natural choosing of “Oh, obviously, I’m going to do more standup.” And I love when improv is really great. I feel like I’m doing it a disservice because I’m not one of those really great improvisers. With sketch, too, I like writing and performing sketch but it’s, right now, a third choice comedy after the TV stuff that I’ve gotten to work on and standup.

Follow Josh on Twitter, visit his website, buy his book, watch the ever popular Last Week Tonight, and listen to Physical Whisper in stores March 18th.