Prolific producer and filmmaker Judd Apatow is behind some of film and TV’s most influential comedies—The 40-Year-Old Virgin, Freaks and Geeks—and has helmed star vehicles for everyone from Amy Schumer to Pete Davidson. For his latest book, Sicker in the Head: More Conversations About Life and Comedy (out now), Apatow dusts off his rolodex to interview high-profile celebrities about their lives and careers, often yielding surprising anecdotes in the process.
The follow-up to 2015’s Sick in the Head features chats with a series of stars including David Letterman, Whoopi Goldberg, Bowen Yang, and John Mulaney. Most occurred mid-pandemic and contain previously unknown tales from the interview subject. Apatow himself shares intimate details, revealing how his 2009 film Funny People was inspired by his mother’s death, advice he gave to his daughters about the industry, and the big names he couldn’t nab for the book (maybe next time, Meghan Markle).
Ahead, several of the wild industry stories and personal confessions to come from Sicker in the Head:
Tom Cruise Visited the Set of Knocked Up
During a September 2020 conversation with Jerry Maguire filmmaker Cameron Crowe, the pair recalled Cruise and Crowe’s visit to the set of 2007’s Knocked Up. (This is around the time that Cruise reportedly pitched Apatow and the film’s star, Seth Rogen, on Scientology.) “I remember Leslie [Mann, Apatow’s wife and frequent collaborator] was about to shoot something, and I had to go to Leslie like, ‘Tom Cruise is here. He’s watching. And Cameron Crowe’s watching, too,’” Apatow recalled. “Because Leslie read for you for Jerry Maguire and got really down to the end, and she didn’t get the part. And the letter you wrote telling her that she didn’t get the part gave her so much confidence.”
Mindy Kaling Had a “Frenemy” at The Office
Kaling and Apatow bonded over her first film role, which was opposite Paul Rudd in The 40-Year-Old Virgin. She recalled her naiveté during shooting, which also extended to the film’s premiere. “I had a frenemy at The Office, and I asked this person, ‘Hey, what do you wear to a premiere?’ And they said to me, ‘Oh, just wear jeans and a T-shirt. It’s L.A. so nobody really gets dressed up for these things,’” she said. “I was like, Okay, cool, because I didn’t want to seem thirsty wearing a gown while everyone was dressed down. So, I showed up in a tank top and jeans with some earrings, and everyone there looked so good—they had been styled to perfection—and I was like, I’ve been fucking duped by this frenemy of mine.”
Stephen Sondheim Helped Make Hamilton Possible
Speaking to Apatow in August 2020, a little more than a year before Sondheim’s passing, Lin-Manuel Miranda shared the mentoring role he played during the creation of Hamilton. “He was one of the first people I told about Hamilton, because he asked what I was working on next,” Miranda said. “At that point, I just had the one song, and he threw his head back and laughed and said, ‘That is perfect. No one will expect that from you.’ And that laugh was enough to power three years of writing.”
NBC Wanted Jerry and Elaine to Be Married on Seinfeld
George Shapiro, manager of Jerry Seinfeld and producer on the long-running sitcom, revealed that NBC brass wanted Jerry and Elaine to be husband and wife. “After doing the first four episodes, NBC gave us this note saying they would like Jerry to marry Julia Louis-Dreyfus,” he told Apatow in June 2018. Cocreator Larry David was vocally against the idea. “Because, then, Kramer and George would be superfluous. They’d be dropping in and out as neighbors instead of being an essential part of the show, and that’s the show. It’s about four friends in New York City,” Shapiro said, claiming that David threatened to leave the show over the note. “That’s the artist Larry is. He said, ‘That’s all I’m going to do, because I don’t think I have more than four shows in me anyway.’ That’s a quote from Larry David, ‘I don’t think I have more than four shows in me anyway.’”