When he was a 15-year-old high school student in Syosset, New York, Judd Apatow got a job at the school radio station and discovered that—holy shit—he could interview the people he admired. All of those people happened to be comedians. The writer/director/producer-to-be (Freaks and Geeks, Knocked Up, 40-Year-Old Virgin, This Is 40) spent 1983 and ’84 picking the brains of his favorite funny people, from Henny Youngman to Howard Stern, and actually held on to the cache of interviews (“My wife calls this hoarding,” he jokes) and continued interviewing comedians as an extremely famous adult with access to other extremely famous people. To raise money for Dave Eggers’s literacy charity 826, Apatow compiled the interviews, new and old, into the book Sick in the Head: Conversations About Life and Comedy, a hefty volume rife with wisdom and stories and confessions from some of the funniest people on the planet. Apatow called us from his LA office to talk about the book in advance of his Chicago Humanities Festival appearance on June 18. He also performs stand-up that night as part of the Trainwreck Comedy Tour, featuring members of the cast of the film, directed by Apatow and written by and starring Amy Schumer.
I did. I was watching Amy [Schumer] do so much stand-up that I got jealous. I hadn’t done it in a serious way since 1992. I said to her, “Give me some premises for jokes, and I’ll write the jokes. And then when we get to New York to shoot the movie, I’ll get up onstage.” Every day her and her sister Kim would send me ideas—like, “What if you had boys instead of girls?”—and I’d write jokes, and then when we went to New York I got up at the Comedy Cellar and it went all right the first time—they were very nice to me at the Comedy Cellar. So every day after work I would go up and do stand-up—I just felt like it woke up my brain. It’s important to talk directly to the crowd and get a feel for what people are thinking and what they think is funny. It helps me as a director in some way. During the shoot we talked about how many comedians there were in the movie and it would be fun to do a Trainwreck tour. We’re coming with Dave Attell and Mike Birbiglia and Colin Quinn and Vanessa Bayer and Amy—it’s like our Coachella. All of the money goes to charity in Chicago—that we were superexcited about. It goes to Youth Guidance and another place, Chicago’s Urban Warriors, a YMCA charity.
A logistical question: How were you able to interview Seinfeld in his West Hollywood apartment when you were a high school student on Long Island?
It’s a debate that people have in the book: Do you have to be damaged, or can you just be born with some sort of talent or insight? I think it’s different for everybody. There certainly are people who are working things out by being creative. And then there are other people who are smart and funny and don’t seem to be that troubled.
Is there anyone you wanted to interview who you weren’t able to or who wasn’t willing to sit for an interview?
Yeah, I love Chicago. It’s one of the few cities I try to go on vacation to. I was there a few months ago with my daughter. We went to Second City and we saw Pearl Jam at Wrigley Field. I love it there. If I was 20 years old, I would sign up for classes at Second City or iO—that’s, like, the ultimate life I wish I lived. v
Trainwreck Comedy Tour: Amy Schumer & Friends Thu 6/18, 7:30 PM Harris Theater 205 E. Randolph 312-334-7777harristheaterchicago.org $100
