Judd Apatow is full of questions in Sick in the Head Credit: Courtesy Random House

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.

You’re promoting a book and a movie at the same time—if you could do it all differently, would you?

Eh, you know, I’m so excited to have the book out there. I’ve been thinking about putting these interviews together for a really long time. And I was talking to Dave Eggers—who runs these charities where they provide free tutoring and literacy for kids, [it’s] called 826—and we were trying to think of ways to raise money for it, and I thought, “Maybe I should chuck all these interviews together in a book.” And he sold it. It gave me an excuse to hunt down a lot of people I wanted to speak to. That was really fun for me. You don’t really have an excuse usually to ask people penetrating questions about their work. You can’t do it at dinner, so it gave me an excuse to be very aggressive with people.

And you’ve started doing stand-up again.

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.

You mention in your interview with Chris Rock that your wife, actress Leslie Mann, hadn’t seen you do stand-up but was going to for the first time. How was that?

It was fun to have her come, and the kids have come a bunch of times. You know, so much of what we do is very stressful. You work on a movie for years, and then you find out quickly if people like it or not. It’s fun to do stand-up because it goes well or it doesn’t, and then you do it again the next night. Then it just disappears. It doesn’t haunt you for the rest of your life.

A part of the book that stuck with me was Albert Brooks talking about liking two parts of the moviemaking process, but hating the third part, when you start getting notes from the studio and all that. Has that been your experience at all?

We’ve been lucky because I have such good partners at Universal Studios. They really get the type of movies we’re trying to do, but it took me decades to find people who understood our sense of humor. I definitely had my moments before then—that’s why all my TV shows got canceled. There was always a conflict of one kind or another, because I didn’t know how to find, you know, networks and studios who knew how to help me.

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?

Well, my grandmother lived in Beverly Hills. I had one trip to visit her, and on that one trip I interviewed Jerry Seinfeld and Paul Reiser and a few other people. They were some of my favorite comedians. I’d see them on The Mike Douglas Show and The Merv Griffin Show, and as a little kid I just had oddly good taste in comedians. When I sat down with [Seinfeld] it was very instructive. I asked him, “How do you write a joke? How do you become a comedian?” And he told me. It’s a really interesting interview because it would be helpful to anyone trying to become a comedian today. What I like about the book is that a lot of it is very funny, but it does talk about the life of an artist or a creative person, what leads you to want to lead that kind of life—and people were very open about their struggles and where their creativity fits in. I feel like it’s something that everyone is amused by, but especially anyone who’s trying to get into the arts—acting, writing, directing, even painting—would take something from how these people approach their work.

I thought the Roseanne interview was particularly deep. She shared so much about her mental health struggles.

Roseanne gave me one of my first jobs writing jokes for her stand-up act. I’ve known her for a long time, and it was interesting for me to just ask her the obvious questions. What was that like when you got famous? What was going on when everything seemed so crazy? How were you perceiving it? She was very frank about it. She really is a genius and changed television in a lot of ways, and I don’t think she gets the credit she deserves. I don’t think there’s been a show like it since.

The book’s operating logic seems to be that every comedian has something in their past that fucked them up just enough to make them funny or to make them want to perform. Did you find that to be true largely?

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.

In the early interviews, your lines of questioning are sophisticated for a 15-year-old. Do remember feeling any pressure to be funny or impress these people?

I was so terrified most of the time and so excited to talk to everybody. It really felt like a lifeline—this is what’s going to help me survive in life. And I’d always have a secret dream that these people are going to want to become my best friends. Like, after the interview they’d just want to keep talking. I had a sense that this was the world I wanted to be in—this was my tribe.

The interviews reveal a lot about your subjects, but you offer a lot of yourself too.

That’s how I tried to approach it. I tried to open up about my journey and then people would tell me something they’d gone through. It’s not so much like a regular interview they’d do with a journalist, because I’m friends with a lot of the people. The vibe is different and they open up more than they might in a more structured type of interview.

Is there anyone you wanted to interview who you weren’t able to or who wasn’t willing to sit for an interview?

I was arranging an interview with Joan Rivers right when she passed away. That was a really sad part of the book. I had only intended to do a few new interviews for the book, and then I started enjoying it so much that two turned into five, which turned into eight or nine. And then I realized who I hadn’t interviewed. Right as I was locking the book I started thinking, “Oh, I should just start the next one now.” Because I didn’t get to interview Will Ferrell or Sasha Baron Cohen or Jimmy Kimmel. I realized how long the list was—Don Rickles, Bob Newhart. There are so many people I admire. Depending on the reaction to the book, it would be fun to do it again.

You interviewed Garry Shandling twice—once in 1984 and then in 2014—and you worked for him early in your career too. Did you ever mention, like, “Hey, I interviewed you when I was a kid”?

No one really remembered the interviews. [Laughs.] The only person who seemed to have some memory of it was a great writer named Alan Zweibel, who was one of the original writers on Saturday Night Live and who’s since gone on to write a lot of great movies and books. And he told me he found the letter I sent him requesting the interview, but I’ve never seen it. He was nice. After the interview he took out his phone book and started giving me Rodney Dangerfield’s home phone number and hooked me up with all sorts of other folks.

Have you spent any time in Chicago at all?

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