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After the success of Virgin, Apatow and his comedy cohorts were essentially given the keys to studio lots. Finding themselves green-lit at every turn, the veteran comic and his close-knit group of friends dusted off their previously snubbed screenplays and took advantage of their opportunity with a nonstop flow of films.
In just four years, Apatow has produced or helped write 10 movies, among them Superbad, Pineapple Express, Forgetting Sarah Marshall and You Don't Mess With the Zohan. He wrote and directed his Virgin follow-up, Knocked Up. He helped make stars out of Seth Rogen, Jonah Hill and Paul Rudd.
Now, Apatow has used his leverage to make Funny People, a plainly ambitious 180-minute film that has Hollywood wondering if he has overestimated his Midas touch.
"People always say that when they become successful that they'll make their passion project," Apatow said in a recent interview.
"But they never do."
For Funny People, Apatow says he fused two ideas: a story about how surviving a near-death experience changes someone, and an abstract analysis of the nature of a comedian. Adam Sandler plays George Simmons, a famous stand-up comedian who finds out he has a form of cancer. Seth Rogen plays Ira Wright, a young stand-up taken in by Simmons.
More than anything, Funny People is overflowing with a love for comedy and all the wealth of experiences of a comedian, from nervously starting out to playing to a roaring packed house. It revels in the backstage banter between stand-ups, the subtlety of good joke-telling, the competitive scrap for fame.
The entire film is imbued with Apatow's life - he has called it "a culmination of my journey in comedy." Apatow's wife, Leslie Mann, co-stars as the girl that got away (from Simmons). Their two young girls, 11-year-old Maude and 6-year-old Iris, play Mann's character's children.
"It's fun to see him grow as a creative person and put those life experiences into his movies," says Mann.
"He's not sticking to the formula of 40-Year-Old Virgin. He's trying new things and experimenting."
The film opens with a home video of a prank call Apatow (41) shot in the early 1990s when he and Sandler were roommates in Los Angeles and both were aspiring comics. ("I was directing Adam badly even then," jokes Apatow.)
Many of the comedians who inspired or worked with Apatow through his career make cameos. One is Paul Reiser (Mad About You) whom Apatow interviewed when he was 15 for his Long Island high school radio show, which he used to gain access to comedians like Gary Shandling and Jerry Seinfeld to learn about the art of comedy.
"In everything - in the songs that I chose, in the comedians that populate it - I just wanted everything to be personal and intimate," says Apatow.
Some have questioned the appeal of a longer and more serious film from Apatow. Los Angeles Times columnist Patrick Goldstein published an open letter to Apatow pleading with him to shorten it.
Apatow says he pitched Universal Studios (which has released all three of Apatow's directed films) exactly the movie he made, length included.
Criticism has recently been nipping at the interconnected Hollywood comedy juggernaut, which Will Ferrell and Adam McKay have also spearheaded. Ferrell's last film, Land of the Lost, did poorly at the box office, fuelling conjecture that an era was dimming.
Mann has seen some change in her husband. Of his circle of friends and performers, she says the conversation has turned from bongs to duvet covers: "Everybody's kind of growing up together."
Ultimately, Funny People asks if it's possible to be both a comedian and a healthy person - whether the old stereotype of the angry, insecure comic is true. As much as anyone, Apatow has sought to disabuse people of that notion by making comedies about earnest, loving (if immature) guys. Increasingly, a sense of family is at the heart of his movies.
In analysing his life in comedy, Apatow came away with one realisation.
"My biggest problem is that as I get older I realise I'm more neurotic than I hoped to be at this age," says Apatow.
"For whatever reason, I'm wired to be thinking about the past and worrying about what's going to happen. When you have a family and kids, you worry all the time."
- Jake Colye.