Obsessed: The Podcast

Judd Apatow on Trump, SNL, and Norm Macdonald

Obsessed: The Podcast

Show Notes

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Judd Apatow chats with Matt Wilstein about his new documentary, Norm: The Tale of Norm Macdonald, and the complicated, singular comedian at its center. Apatow explains why he chose to let Norm tell his own story through archival footage, stand-up, interviews, and the strange truths hidden inside his fake memoir, before revisiting Norm’s infamous firing from Saturday Night Live and the decision to keep going after O.J. Simpson jokes angered NBC executives. They also get into Norm’s complicated relationship with politics, the pressures facing comedians in the Trump era, his later clashes with cancel culture, and the clues Apatow found about the illness Norm kept private until his death. Plus, Apatow opens up about why he thinks Hollywood has become less willing to take risks on comedies, his hopes for The Comeback King, and whether Bridesmaids or Superbad could ever get a sequel. Learn more about your ad choices. Visit podcastchoices.com/adchoices

More from Obsessed: The Podcast

Oct 22, 2026

Comedian and Emmy-nominated writer Nimesh Patel joins Matt Wilstein on Obsessed: The Podcast for a sharp, hilarious conversation about political comedy, free speech, and the line between provocative humor and controversy. Patel discusses his new Netflix stand-up special, By the Dip, including his jokes about FBI Director Kash Patel, the Trump administration, and why he chose to take on some political targets while leaving others alone. He also reflects on his time writing for Saturday Night Live alongside Colin Jost and Michael Che, the evolution of comedy in a polarized political climate, the backlash surrounding Shane Gillis, and his decision to reconsider performing at Saudi Arabia’s Riyadh Comedy Festival. Plus, Patel revisits the Columbia University controversy that thrust him into the spotlight and shares candid thoughts on censorship, cancel culture, and the business of comedy. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Oct 15, 2026

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Oct 10, 2026

Final Destination star Devon Sawa joins Kevin Fallon on Obsessed for a Halloween-season trip through the roles that made him a ’90s crush and a horror icon. He reveals the audience reaction that told him Final Destination was something special, how the movie led Dr. Dre to cast him in Eminem’s Stan video and why Casper still holds a special place in his heart. Sawa also talks about joining fellow ’90s favorite Tiffani Thiessen on the new Freeform series Coven Academy, the nerves he felt before filming a love scene with Jean Smart on Hacks and his pitch for a darker Casper sequel. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Oct 8, 2026

NSYNC’s Lance Bass gets candid about his decades-long friendship with Joey Fatone, sharing how the two became inseparable and revealing hilarious behind-the-scenes stories from their time in the boy band, including a tour tradition involving Jack and Coke in water bottles. Plus, Lance spills stories from Cocktail Wars, discusses reconnecting with his former girlfriend Danielle Fishel, weighs in on the latest Dancing With the Stars cast, revisits his canceled space mission, and gives an update on an NSYNC reunion. From boy-band nostalgia to Hollywood secrets, Lance has plenty to dish about!

Oct 3, 2026

Mean Girls star Jonathan Bennett joins Kevin Fallon on Obsessed to spill behind-the-scenes stories about playing Aaron Samuels, his reign as the Gay King of Christmas, and why he’ll never stop embracing his most iconic role. Bennett reveals how coming out transformed his Hollywood career, why he’s doubling down on LGBTQ+ love stories amid today’s political climate, and what it’s like to make history with Hallmark’s groundbreaking gay Christmas movies. Plus, he dishes on joining General Hospital, hosting Halloween Wars, and bringing more queer representation to mainstream TV. And, of course, we get to the question every Mean Girls fan knows: Does his hair actually look sexy pushed back?

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