With his latest movie, Judd Apatow, creator of Knocked Up and The 40-Year-Old Virgin, tries to blend comedy with cancer. Caryn James on the director's dark gamble.

It’s not easy competing with Judd Apatow, especially when you are Judd Apatow. His new, hugely hyped Funny People is an ambitious, indulgent mess of a movie, with Adam Sandler as a comedian diagnosed with leukemia and given a very bleak prognosis. The idea makes you gag faster than you can say “crying clown alert,” yet this expectation-defying film tosses in enough quirks to make it intriguing.

The movie is not nearly funny or touching enough to sustain its 2 hour and 25 minute running time. But as it flails away, you can almost see Apatow trying to get out from under his own shadow, grappling with a thorny question every director of megahits with a signature style has to face: how to move in a new direction without leaving your old audience behind?

Apatow’s formula—with all those callous-turned-sensitive slobs—is so successful and lucid that his proteges can make an Apatow movie as well as he can. He may be the towering figure in film comedy today, but he has written and directed only two movies: The 40-Year-Old Virgin, and Knocked Up, the accidental-pregnancy comedy that improbably won over women as well as men. A couple of other hysterical comedies, though, compete for the title Funniest Apatow Movie That Apatow Didn’t Make: Forgetting Sarah Marshall (written and directed by Jason Segel) and Superbad (written by Seth Rogen and Evan Goldberg, directed by Greg Mottola). Apatow produced, and he left fingerprints.

Funny People is all his, and as he fumbles with his heavy-duty theme, he doesn’t quite break his old mold, leave it behind, or graft anything terribly fresh onto it. Yet at odd moments you realize this film isn’t going where you thought it was.

For starters, Sandler doesn’t dominate the first half, even though he plays the main character: George Simmons, a famous but friendless standup comic turned movie star. Seth Rogen practically steals the film as Ira Wright, a would-be performer George hires as a joke writer and personal assistant.

Ira is a better comedian than he thinks he is, and soulful enough to be troubled by caring for a dying man who refuses to tell anyone else he’s sick. He is a familiar Apatow mensch, and somehow Rogen gets away with playing this guy over and over without becoming tiresome. As Ira’s roommates, Jason Schwartzman plays a successful actor starring in a schlocky sitcom called Yo’ Teach! and Jonah Hill plays a struggling comic. Add George’s illness and the movie begins to feel like Entourage with standup and death.

Yet Apatow has deliberately scaled back the comedy, and in his most daring touch depicts George as a guy who’s not that funny. We see snippets of his awful movies, which seem to mock Sandler’s own high-concept early work; one has George’s head on a baby’s body. And when George makes a surprise comedy-club appearance, he is so in the grip of his death sentence, his jokes so dark, the crowd is absolutely silent. It’s an edgy and real moment.

Add George’s illness and the movie begins to feel like Entourage with standup and death.

You can feel the typical Apatow comedy straining to break through, though, and even see evidence of it outside the film. Yo’ Teach! is a clever satire of tired sitcoms like Saved by the Bell; in Funny People, there’s a glimpse of the show, but entire mini-episodes are online, worth checking out. Aziz Ansari’s character, a raucous standup named Randy, is hardly seen in the film, but the character has taken on a buzzy life of his own; there’s even a mock documentary about him and talk of a Randy movie. A recent Comedy Central special showed longer versions of some standup routines Apatow shot and didn’t use. The movie could have been funnier if he’d wanted it to be; he made a riskier choice.

Even when you get past expecting Return of Superbad or Knocked Up Again, there’s still a problem. The film’s last section takes a dramatic curve and almost becomes its own sequel when George goes after his ex-girlfriend Laura, the one woman he truly loved, now unhappily married with two children. Apatow’s wife, Leslie Mann, is Laura, and their two small daughters are Laura’s children (just like Knocked Up; Rogen even plays in the backyard with the kids). Eric Bana shows his comic flair as Laura’s husband. Everyone is good, especially the Apatow girls. But there’s no getting around it: This is the indulgent part, which goes on and on and on. There’s pizza; there’s playing with a dog.

That flabby excess is too bad, because something ruthlessly honest is going on. We realize that, sick or healthy, George is a selfish, bitter jerk. And Sandler goes for it; he doesn’t ask the audience to like him any more than George asks Ira for sympathy. This is a great advance for an actor who seemed to sleepwalk through dramas like Punch-Drunk Love and the unbearably mawkish Reign Over Me. Here he and Apatow shatter the cliché of the crying clown.

In the end, Funny People is a timid hybrid. But its daring touches suggest that if Apatow ever sets himself free, really free, from his comfy formula, he might do something amazing.

Caryn James is a cultural critic for The Daily Beast. She also contributes to Marie Claire and The New York Times Book Review. She was a film critic, chief television critic and critic-at-large for The New York Times, and an editor at the Times Book Review. She is the author of the novels Glorie and What Caroline Knew .