Preferred Ways of Failing with Josh Gondelman

First Draft with Sarah Enni

First Draft Episode #210: Josh Gondelman

Josh Gondelman, comedian, TV writer for shows like Last Week Tonight with John Oliver and Desus and Mero, and debut author of memoir Nice Try: Stories of Best Intentions and Mixed Results, talks about coming up in comedy, fumbling his breakout moment with the viral Modern Seinfeld Twitter account, and learning that being a “nice” person isn’t the same as being a good person.

Links and Topics Mentioned In This Episode

• In addition to Nice Try, you should also check out Josh’s standup specials: Dancing on a Weeknight (2019); Physical Whisper (from 2016); and Everything’s the Best! (2011).

• Nancy Kerrigan was the subject of one of the most bizarre crimes in all of sports (really worth watching The Price of Gold, an excellent 30 for 30 documentary about the Kerrigan-Harding incident), which was documented in the film I, Tonya, which Josh’s parents did not see out of loyalty to Kerrigan

• Early on Josh performed in the chorus of The Music Man

• We decide that literary humor is to comedy as Garrison Keillor is to Chris Rock

• Josh wrote a spec script for It’s Always Sunny in Philadelphia

• Josh was contributing to places like McSweeny’s and New York magazine when he first moved to the city

• Josh co-founded the @SeinfeldToday Twitter account with his friend Jack P. Moore (playwright and sitcom writer for shows like Dear White People), which went viral and got him lots of professional opportunities

• Josh made an impression on Jim Gaffigan with a joke about the wisdom of the justice system in D2: The Mighty Ducks when he was getting his feet wet as a standup in New York City

• Josh talks about establishing authority as a standup onstage, which reminded me of Pete Holmes addressing how he looks (more like a youth pastor than a comedian) on his 2013 special, Nice Try, The Devil. You can see a great example of Josh doing something similar in his 2019 sets on Late Night with Seth Meyers and The Late Late Show with James Cordon. Josh also got advice and encouragement about this from fellow comedian Pete Lee.

• Josh got a big win when he was able to write for Billy on the Street, featuring Billy Eichner

• One of the notable segments from Last Week Tonight with John Oliver was an early one about net neutrality, with a bit at the end (which Josh credits to Geoffrey Haggerty, a comedy writer for shows like The Daily Show and Last Week Tonight with John Oliver) calling for viewers to write in to the FCC. So many viewers wrote to the FCC that its system crashed, and the government investigated whether the onslaught of feedback was from actual citizens or a coordinated DDoS attack.

• Tim Carvell, head writer for The Daily Show who left with John Oliver to create Last Week Tonight with John Oliver

• Josh is now the producer and writer for Desus and Mero on Showtime. Before he wrote for them, he was a fan of Desus and Mero’s podcast, Boedga Boys, and their TV show, Desus & Mero, on VICELAND.

• Josh does pep talks on Twitter from time to time, and initially was approached to write a book based on that premise. But he resisted that idea because internet darling Jonny Sun (playwright, academic, and author and illustrator of Everyone’s a Aliebn When Ur a Aliebn Too -- listen to Jonny Sun’s episode of First Draft here) had already illustrated the famous Twitter pep talks written by Lin-Manuel Miranda (actor, composer, and playwright of Hamilton and In the Heights) for the book, G’Morning, G’night!: Little Pep Talks For Me & You.

• I was reading Brené Brown’s Daring Greatly: How the Courage to be Vulnerable Transforms the Way We Live, Love, Parent, and Lead, at the same time as Josh’s memoir, which actually was a beneficial co-reading experience (FTR I also recommend Brown’s The Gifts of Imperfection: Let Go of Who You Think You’re Supposed to Be and Embrace Who You Are on audiobook! It’s read by Lauren Fortgang and she does a great job!)

• Josh was on a panel with journalist and author Liz Plank--whose most recent book, “For the Love of Men: A New Vision for Mindful Masculinity”, is on sale now!--about shifting concepts of masculinity

• Nikki Glaser, a comedian and radio host who Josh admires, gave him pivotal advice early in his career

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Every Tuesday, I speak to storytellers like Veronica Roth, #1 New York Times bestselling author of Divergent; Linda Holmes, New York Times bestselling author and host of NPR’s Pop Culture Happy Hour podcast; Jonny Sun, internet superstar, illustrator of Lin-Manuel Miranda’s Gmorning, Gnight! and author and illustrator of Everyone’s an Aliebn When Ur a Aliebn Too; Michael Dante DiMartino, co-creator of Avatar: The Last Airbender; John August, screenwriter of Big Fish, Charlie’s Angels, and Charlie and the Chocolate Factory; or Rhett Miller, musician and frontman for The Old 97s. Together, we take deep dives on their careers and creative works.

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