Preferred Ways of Failing with Josh Gondelman

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


I want to hear from you!

Have a question about writing or creativity for Sarah Enni or her
guests to answer? To leave a voicemail, call (818) 533-1998. You
can also email the podcast at firstdraftwithsarahenni@gmail.com.
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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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