Judd Apatow Reveals Brad Pitt/ Rolling Stones Movie That Never Was

Writer/director shares behind-the-scenes details from his early career as part of MTV Pioneers speaker series.

Just ahead of the release of his latest comedy, “This Is 40,” and the potential end of the world, award-winning writer/director/producer Judd Apatow graced the New York offices of MTV with an hour of behind-the-scenes stories and general hilarity as part of our MTV Pioneers speaker series.

The event was chock-full of entertaining information, including the best moment of Apatow’s life (via a lengthy story about an ill-fated Rolling Stones movie co-starring Brad Pitt and Ben Stiller that never came to fruition), dealing with his daughter’s 100,000-plus Twitter followers and his own decision to stop following Kanye West. Here are our favorite moments from the chat:

The best moment of Apatow’s career and the Rolling Stones/Brad Pitt comedy that never was
Once upon a time in the early-to-mid-’90s, Apatow and Ben Stiller wanted to make a comedy that revolved around two average guys — one to be played by Stiller and the other to be played by “that young guy” Brad Pitt. “The idea is Ben and Brad Pitt have these crappy jobs and they’re both obsessed with the Rolling Stones and they’re going to follow them across the country,” he explained. The project moved far enough along to have Pitt on-board and to win the support of the Stones after Apatow and Stiller went to Toronto to pitch them the idea during a rehearsal.

“They told us they’d do it, and they let us watch them rehearse for three hours,” he recalled. “We’re alone in a gym at a high school and the Stones are just playing for us. And this is my best showbiz moment ever: In the middle of the rehearsal, Mick Jagger walks over to me and Ben and says, ‘You guys OK? You need a glass of water?’ I said to Ben, ‘This is the best moment ever — don’t forget it.’ ”

Unfortunately, the project fell apart because Pitt decided to do “Seven” and it turned out to be impossible to film the Stones while they were on tour.

When Jerry Seinfeld taught Apatow how to write jokes
In high school Apatow started his own radio show as a way to interview his comedic heroes. This led to conversations with Weird Al and Howard Stern and an explanation on how to write jokes from Jerry Seinfeld. “I remember going to his apartment in California and him opening the door and not at all expecting to be interviewed by a child,” Apatow recalled. “But he walked me through how to write a joke, that you needed a great premise. What a nice guy to do that. I wouldn’t do that for you.”

The long-term effects of “Freaks and Geeks” getting canceled
Speaking of the impact that the early and preemptive cancellation of cult favorite TV show “Freaks and Geeks” had on his psyche, Apatow admitted that he’s never really gotten over the tragedy of it all. Because of that, he’s continued the series in his own way.

“It felt like a magical moment that should have been allowed to continue,” he said. “I kind of lost my mind from that, and in a way everything that I’ve done since has been a way of pretending ‘Freaks and Geeks’ was never canceled. ‘Knocked Up’ in a way was just Ken Miller [Seth Rogen] from ‘Geeks’ getting a girl pregnant; ‘Forgetting Sarah Marshall’ is Nick Andopolis [Jason Segel] falling in love and being tortured by it.”

Dealing with his daughter’s 100k Twitter followers
In addition to acting in his films, Apatow’s 15-year-old daughter Maude has a solid presence on Twitter, with more than 100,000 followers. “We’ve allowed her to be exposed to 100,000 strangers who can speak to her directly. Is that a good parenting choice? I don’t know,” he joked before adding that he is confident she knows how to conduct and protect herself accordingly. “The flip side of it is on something like Twitter she’s developed her voice. She knows how to be funny, how to be insightful without being obnoxious and knows how to block people if they’re being nasty,” he said. “I worry more about will she have the ability to write anything longer than six sentences.”

Living with Adam Sandler and his pre-fame charisma
When I wanted to be a performer I would hang out with comedians. You wanted to be friends with the people you thought were really talented, so I would hang out with Adam and Jim Carrey,” Apatow explained of his early days as a stand-up comedian, during which he lived with Sandler in Los Angeles. “Everyone knew it around Adam,” he said of predicting that Sandler would eventually be famous. “He had charisma. It’s a funny thing when you’ve been around people who get really famous. Their charisma exists before they’re famous, so in that era he would go somewhere and you would feel that people were drawn to him and not drawn to me.”

How famous musicians like Eminem end up in his movies
“It is just an elaborate way to get Eminem to talk to me,” Apatow said of the rapper’s cameo in 2009′s “Funny People .” “Adam Sandler knows him a little bit and we asked him to do it and he said ‘yes.’ ” Apatow went on to say that Eminem was game for being made fun of a bit and fully embraced his verbal assault of Ray Romano in the heat of that scene. “We were laughing so hard. Afterwards I told Ray how funny it was, and he said, ‘You think it would be funny if Eminem could kick my ass? Is it so funny to think that I can’t defend myself?’ And I said, ‘Yes.’ ”

Why Kanye West lost him as a Twitter follower
“He would just show pictures of purses he liked, and I was like, ‘I can’t do it,’ ” Apatow explained of why he stopped following West, who was one of the first four people Apatow followed on the site. “I would follow him and try to engage him and he never tweeted back at me. I would send these really funny Tweets and he would show a picture of the car he liked. … He’s awesome — I’m a big fan of his — but I’m not a big fan of his showing me sweaters.”