For the first several years of his career, stand-up comedian Matteo Lane would open his sets by telling the audience, “Obviously, I’m gay.” At a certain point, he got tired of coming out to a room of strangers every night and instead begins his new Hulu hour ‘The Al Dente Special’ by making fun of the way white women talk—a bit that delighted Gayle King and led to one of the more awkwardly hilarious morning TV moments in recent history. In this episode, Lane explains why he decided to give the ‘CBS Mornings’ host a pass for repeating the “f-slur” back to him and reveals how King’s fellow astronaut Katy Perry ended up being part of his special as well. And as Pride Month comes to a close, he discusses why he’s sick of people expecting gay comedians to relive their trauma, shares why he avoids talking politics on stage, and calls out TV bookers for keeping him off of late-night TV because they deemed his act “too gay.”

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Over the course of his 40-year career, Larry Charles has had two central creative relationships with Larry David (‘Seinfeld’ and ‘Curb Your Enthusiasm’) and Sacha Baron Cohen (‘Borat’ and ‘Brüno’). Now, he reveals in a new memoir that he hasn’t spoken to either man in years. In his return to The Last Laugh podcast, Charles breaks down how it all fell apart with two comedians he still considers complicated geniuses. He shares stories about how ‘Seinfeld’ solved its early Elaine problem after Julia Louis-Dreyfus came to the creators sobbing and reveals why a young David Sedaris turned down an offer to write for ‘Seinfeld.’ Charles also discloses what exactly it was about his HBO documentary that Larry David couldn’t stand, shares his thoughts about friends Bill Maher and Cheryl Hines flirting with MAGA, explains why there was a time he would have literally “died” for Sacha Baron Cohen and what went so wrong with their final collaboration ‘The Dictator.’

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Justine Lupe thought there was no way she’d ever be able to top the experience of playing Willa on HBO’s ‘Succession.’ Then she got cast as Morgan, one of the “loser siblings” on the runaway Netflix hit ‘Nobody Wants This.’ They are two very different roles on two very different shows, but she says on this episode that she feels extremely “lucky” to get the opportunity to show both comedic and dramatic sides of herself on each. Fresh off of wrapping filming for Season 2 of ‘Nobody Wants This,’ Lupe talks about the pressure of satisfying fan expectations for her character’s complicated relationship with Timothy Simons’ Sascha. And she opens up about her deeply rewarding experience on ‘Succession,’ which was only supposed to be a handful of episodes before Willa became a central character, and even part of the Roy family, all the way until the very end.

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25 years ago, Kevin Smith released his most controversial and provocative film. Then, after a solid run in theaters and a robust life on VHS, it disappeared into the ether and has never been available to stream. Now, as ‘Dogma’ makes its triumphant return to theaters this weekend, Smith reveals the full story of how he got huge stars like Matt Damon, Ben Affleck, George Carlin and others to appear in his audacious satire of the Catholic Church, how he was able “rescue my movie about angels from the devil himself” Harvey Weinstein, how a planned sequel will change now that he has fully lost his own faith, and so much more. Plus, Smith confirms the Oscar-winning actors who almost played God before Alanis Morissette got the coveted role and reveals the major Hollywood job he turned down to focus on finishing his greatest film.

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You might recognize Richard Kind from sitcoms like ‘Mad About You’ or ‘Spin City.’ Or from his voice work as the imaginary friend Bing Bong in Pixar’s ‘Inside Out.’ Now, he has become the ultimate late-night TV sidekick on ‘Everybody’s Live with John Mulaney,’ which wraps up its first season run on Netflix this week. In this episode, Kind talks about what it’s like to be just famous enough to work all the time but not famous enough to play himself on ‘Curb Your Enthusiasm.’ He also shares showbiz stories about almost getting cast on ‘Seinfeld,’ playing Rudy Giuliani in the film ‘Bombshell’ and offers up some very strong opinions about Woody Allen.

This episode was originally published on July 14, 2020.

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Jillian Bell has a bad habit of talking herself out of acting jobs. She was supposed to play a much bigger role in Adam Sandler’s ‘Murder Mystery 2’ and almost starred in one of Netflix’s biggest hit shows. So when it came time to make her directorial debut ‘Summer of 69’ (now streaming on Hulu), she decided to stay (almost entirely) behind the camera. In her return to this podcast, Bell talks about casting SNL’s Chloe Fineman as a stripper fairy godmother-type character opposite newcomer Sam Morelos in her surprisingly sweet teen sex comedy. She also gets into her own complicated history with SNL 15 years after she spent one season at the show as a writer who desperately wanted to be in the cast. Plus, Bell reveals what it was like to reprise one of her first TV roles in the series finale of ‘Curb Your Enthusiasm’ and tells a deeply embarrassing story about the first and only time she met Justin Timberlake.

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For most of his career, Kumail Nanjiani has been asked to play the same type of brash nerd character that he perfected over six seasons on HBO’s ‘Silicon Valley.’ Then, a few years back, everything changed. The Pakistani-American comedian transformed his body to appear in the Marvel movie ‘Eternals’ and ever since, strange new doors have opened for him in Hollywood. One of those unexpected opportunities came when Natasha Lyonne reached out to him to play the bleach-blonde-haired, heavily tattooed Florida panhandle cop named Gator Joe on this week’s episode of her Peacock hit ‘Poker Face.’ At first, he thought she might have been joking. In this episode, Nanjiani talks about how he nailed the character’s very specific Southern accent only days before they started filming. Then, he looks back at the earlier part of his career, including how close he came to playing Abed on ‘Community,’ what he learned about “amoral” tech giants like Elon Musk through ‘Silicon Valley,’ and the deeply rewarding experience of bringing his real-life story to the screen in ‘The Big Sick.’ And he also discusses his long-awaited return to stand-up comedy with his first special in 12 years set to hit Hulu later this year.

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Kerri Kenney-Silver never thought she’d get a part like Anne on ‘The Four Seasons.’ After more than two decades playing the disturbingly odd Deputy Trudy Wiegel on ‘Reno 911!,’ the 55-year-old actress believed Hollywood saw her as little more than outrageous comic relief. But then Tina Fey gave her the gift of a lifetime by casting her opposite Steve Carell on Netflix’s latest hit series. In this episode, Kenney-Silver talks about finding the nuance in what could have been a stereotypical caricature of the jilted ex-wife. And she also discusses co-founding perhaps the most successful college sketch comedy group of all time with The State, the terrible career advice she gave her one-time co-star Ellen DeGeneres, and the bizarre longevity of ‘Reno 911!’

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