Now What?: Josh Gondelman on His New Stand-up Album and Last Week Tonight

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Now What?: Josh Gondelman on His New Stand-up Album and <i>Last Week Tonight</i>

There are plenty of venues for comedians to get their voice heard today, and if they’re any good, they’ll use each and every one of them. No one exemplifies this better than Josh Gondelman. Originally from Boston, the 31-year-old has, since moving to New York to pursue bigger stand-up opportunities, kept himself busy writing comedic pieces for magazines and working for shows like Billy On The Street.

His biggest success, though, came via the parody Twitter account @seinfeldtoday that he created with his friend Jack Moore, which offers up short and absurd synopses of Seinfeld episodes if they were still being produced today. That brilliantly funny and pointed account has landed over 860,000 followers and helped Gondelman score some other coups like his recently released book, You Blew It: An Awkward Look at The Many Ways in Which You’ve Already Ruined Your Life (co-written with Jack Berkowitz), and his current job as a staff writer for Last Week Tonight With John Oliver. Today he releases a new stand-up album, Physical Whisper, through Rooftop Comedy.

Through it all, Gondelman has continued his fine work as a stand-up, where he brings his skewed point of view to bear on his awkward experiences with women, his dealings with family, and his feud with the maker of a spray that helps premature ejaculators numb their junk. At least that’s what you’ll find on his recently released album Physical Whisper. We recently spent some time on the phone with Gondelman to talk about his career as a stand-up and his many projects, and walked away with some insight into the work he’s doing for the Peabody-award winning Last Week Tonight.

Paste: When you started doing comedy, especially in New York, how did you balance out doing stand-up with your work writing for magazines and TV shows?

Josh Gondelman: When I started out doing comedy, I was still in college and was working day jobs. I taught preschool for a few years. And then I got more into freelance writing. So stand-up has always been my primary independent creative mode of expression. I’ve done it my whole adult and young adult life. It’s definitely a passion and something I’m interested in and excited to do. Now that I’m working full time at Last Week Tonight, I don’t have as much time to devote to stand-up, but I definitely feel at my best when I’m getting on stage and writing new stand-up jokes as well.

Paste: What inspired you to doing stand-up, then? Was it a particular stand-up or an album that you grew up with?

Gondelman: I always loved jokes. It’s such a dumb, facile thing to say, but it’s true. I remember being a kid and getting those joke books from the Scholastic book club and loving comedy from a very young age. VHS recordings of SNL when I was too young to stay up and Mel Brooks. I was pretty much a comedy omnivore. I remember we were members of the BMG Music Club where you’d get 12 cassettes or CDs for a nickel. My dad helped me curate a selection but I just got ones that I heard of: 2000 Year Old Man, Ellen Degeneres’ stand-up album, Jeff Foxworthy’s You Might Be A Redneck album, and the last one was Bill Cosby’s Greatest Hits, Volume One, which as an artifact has aged less well. It’s always been an interest of mine. Then after my freshman year of college, a friend of mine had started doing stand-up around Boston, so all our mutual friends kind of goaded me into doing it.

Paste: And how was your first time doing stand-up?

Gondelman: Probably not great. I don’t remember it well, but I definitely have those rose-colored glasses for the past where…I remember the first time I ever did well kind of viscerally. I remember that feeling as good as having a good set now feels. It’s definitely a different thing. I’m certainly better as a comedian and get better and more frequent laughs than the first time I ever had a good five-minute set, but it kind of feels the same. Which is good because if it only felt commensurate with how good you actually were you would just dry heave for your first couple of years.

Paste: How long did it take you to feel like you found your voice and knew how to write for yourself?

Gondelman: I still feel like that there’s stuff that I wish I were capable of onstage. But every time I write a joke that I’m happy with, for the time that I’m pleased with it. “Ooh, this is starting to work. Now I’ve got it! I’ve got it and I’m the man I’ve always been meant to me.” As soon as the joke works steadily and it’s not changing as much and shifting, and I can make my way through it instead of feeling it out. I know where the beats are. Once I get to that point, there’s always a terror of, “Well, that’s the last joke I ever wrote, and from now on I’m a fraud coasting on fumes.” I feel like I always have a push and pull of, “Oh great, I’m doing it, and I’m getting a handle on this.” On the other hand, it’s, “I’ve accomplished all I’ll ever accomplish and I will never do anything of value ever again.”

Paste: That sounds very familiar to the way my mind works as a writer. Once I finish something, I think, “That’s great. Now what?”

Gondelman: “Now what?” is such a big feeling. I think you need a little “Now what?” but not too much. A little pushes you to do the next thing, but a big “Now what?” means you’ll never feel happiness or satisfaction.

Paste: How do you think growing up in Massachusetts and doing comedy in Boston informed your voice as a comic?

Gondelman: I love Boston and I had a very lovely childhood in Massachusetts. Even if you’re a gentle person…I’m kind of a twerp…it hardens you as a twerp, so you become a nerd who really likes sports or someone who does visual arts but has a great empathy for road rage. It puts a little edge on you that’s helpful for doing creative things in a practical way. Especially doing stand-up in Boston, unless you only frequent a couple of the friendliest, nicest places, the crowds are a little more aggressive and harder to impress. And I think that’s a nice refining experience for a comedian. It’s an artform that has to bring predictable, tangible results. You can’t be, like, “Well, you just don’t get my art.” Really if you’re not getting laughs, maybe you’re not doing the art that you say you’re doing. I really value, especially now, having to come in all sorts of different situations whether it’s charity fundraisers for a little league team at an Elks Lodge or clubs in the city or little alternative venues around the city. There’s really any kind of show you’d have to do, which is cool.

Paste: I hear that a lot from different comics about having to make those adjustments to fit an audience or whatever room you’re playing in.

Gondelman: Not only having to adapt to an audience but how to do a version of you that works as many places as possible. Without becoming a person whose only concern is, “What can I do that everyone will laugh at?” Because if that’s your only standard, then the best stand-up in the world would be a YouTube video of a guy getting bit in the nuts by a dog or something. I like the challenge of going, “Here’s what I like to do. How can I translate to the most diverse set of audiences?” I try not to be precious about what I think is a good joke but I will try to make what I think should work work. It doesn’t do anyone any good for me to go, “No, this is good,” and every audience disagrees. It’s nice to form a consensus of, “Here’s what I think is good and I can make it work in a few different places so it must have some merit at that point.”

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