'Awards Chatter' Podcast — Josh Gondelman ('Last Week Tonight' & 'Desus & Mero')

The rising-star comedian and writer, who won three Emmys and two Peabodys for his contributions to HBO's John Oliver vehicle before moving over to Showtime's first late-night show, reflects on venturing into stand-up, co-creating Modern Seinfeld and working with talents spanning the spectrum of senses of humor.
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Josh Gondelman

"I had been at Last Week Tonight for five years, I had learned so much, I really cut my teeth there in terms of writing for the medium of television, my joke writing is so much stronger for having been there, I just read so much and watched so much documentary footage that I'm a smarter person for having been there, but I was like, 'You know what? This is interesting,'" says Josh Gondelman, one of the top young figures in the world of late-night comedy, about the offer that lured him earlier this year from his job at John Oliver's aforementioned HBO show to another as a writer — and a supervising producer — at Showtime's first-ever late-night show, Desus & Mero, which is hosted by thirty-somethings from the Bronx, as opposed to a forty-something from Birmingham, England.

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LISTEN: You can hear the entire interview below [starting at 20:34], following a conversation between host Scott Feinberg and Gil Robertson, an entertainment journalist who is also the co-founder and co-president of the African-American Film Critics Association.

Past guests include Steven Spielberg, Oprah Winfrey, Lorne Michaels, Barbra Streisand, George Clooney, Meryl Streep, Robert De Niro, Jennifer Lawrence, Eddie Murphy, Gal Gadot, Warren Beatty, Angelina Jolie, Snoop Dogg, Jessica Chastain, Stephen Colbert, Reese Witherspoon, Aaron Sorkin, Margot Robbie, Ryan Reynolds, Nicole Kidman, Denzel Washington, Julia Louis-Dreyfus, Matthew McConaughey, Kate Winslet, Jimmy Kimmel, Natalie Portman, Chadwick Boseman, Jennifer Lopez, Ricky Gervais, Judi Dench, Quincy Jones, Jane Fonda, Tom Hanks, Amy Schumer, Justin Timberlake, Elisabeth Moss, RuPaul, Rachel Brosnahan, Jimmy Fallon, Kris Jenner, Michael Moore, Emilia Clarke, Lin-Manuel Miranda, Helen Mirren, Tyler Perry, Sally Field, Spike Lee, Lady Gaga, J.J. Abrams, Emma Stone, Ryan Murphy, Julia Roberts, Jerry Seinfeld, Dolly Parton, Will Smith, Taraji P. Henson, Sacha Baron Cohen, Carol Burnett and Norman Lear.

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Speaking at the offices of The Hollywood Reporter during a recording of THR's Awards Chatter podcast, the 34-year-old, who is also a stand-up comedian and author, says of his new bosses, Desus Nice and The Kid Mero, "I like these guys. It is so different in vibe [from Last Week Tonight]. I would get offers occasionally like, 'Hey, we want to do the John Oliver Show of economics' or 'the John Oliver Show of science,' and it just wasn't that interesting to me to chase the spectre of, 'Well, he's doing it the best, so we'll just try to do his thing.' But with these guys, I was like, 'Oh, this will be so interesting — and different.'"

Gondelman, a 2007 graduate of Brandeis University, first made his name in 2012 as the co-creator, with Jack Moore, of the Modern Seinfeld Twitter account @SeinfeldToday, which became a viral sensation and won the best parody account Shorty Award. He ultimately was able to parlay that job into one on the staff of the just-launching Last Week Tonight, where his responsibilities initially centered on interactive programming — in other words, engaging viewers of the show online, as he had done with Modern Seinfeld — and then quickly increased when he became a full-fledged writer.

Gondelman and his fellow Last Week Tonight writers, with their funny quips and enraging deep-dives into injustices, won Peabody Awards in 2014 and 2017; were nominated for and won the best comedy/variety talk series Writers Guild of America Award in 2017, 2018 and 2019; and were nominated for the best writing for a variety series Emmy in 2015, 2016, 2017, 2018 and 2019, winning in 2016, 2017 and 2018. (The Last Week Tonight writers, including Gondelman, even though he departed mid-season, are Emmy-nominated again this year.)

Desus & Mero previously existed, in a less polished form, from 2016 through 2018 at Viceland, where the hosts had no writers and aired once a week. Now, at Showtime, they have a full staff and air twice a week, all on top of regularly posting episodes of their hugely popular podcast The Bodega Boys. Says Gondelman, who recently released his third comedy album (Dancing on a Weeknight) and whose second book will be published on Sept. 17 (Nice Try: Stories of Best Intentions and Mixed Results), "I'm learning these different skills that I wasn't going to get in just a writing position. I'm helping to supervise edits of things, I'm out in the field on shoots every once in a while, I'm involved in higher-level meetings seeing a little more of how decisions get made and having a little input. So that was a really thrilling opportunity, to get to be at the beginning of something again."