It’s a simple truism that funny people are often angry people, and angry people are often sad people. Humor, to funny people, is a coping mechanism; if the world can be made into a joke, if something horrible or offensive can be deflated without violence, then life becomes manageable.

This paradox—that comedians often have very little to laugh about—is the driving concern of Funny People, writer-director Judd Apatow’s first step into the serious business of comedy.

Adam Sandler plays George Simmons, who is for all intents and purposes a lonelier clone of Sandler himself. Simmons is wildly successful and popular, but he doesn’t seem to take any comfort from that; his life is spent in a cavernous mansion populated fleetingly by servants and groupies. When his doctor gives him a grim prognosis—a rare form of leukemia and about a year to live—Simmons seems ready to spiral the drain completely.

It’s at a stand-up gig that Simmons—spinning dark material reminiscent of the latter shows of the comedian Bill Hicks, who died of pancreatic cancer at age 32—meets Ira Wright (Seth Rogen), a struggling comedian with good material and poor delivery. Simmons hires Wright as a joke writer, assistant, and friend-for-pay.

Simmons is not an easy man to work for. Their relationship, mostly contentious and never “warm,” takes a harder turn yet when Simmons decides that, to get his life (or what’s left of it) back on track, he must reclaim the “girl who got away” (Leslie Mann, Apatow’s wife). And Simmons doesn’t much care if, in the process, he destroys the family she’s part of now.

This is an unwieldy story arc, to say the least. Apatow is fond of crafting stories that move from plot point to plot point without seeming to. His movies are meant to simulate the ebbs and flows of real life, a tactic that worked so well in The Forty-Year-Old Virgin, his breakout hit, and a little less effectively in Knocked Up, which made Seth Rogen a leading man.

Funny People rambles at great length, and at times loses all momentum during its aimless middle passages. It’s well over an hour into Funny People’s 146-minute running time before Simmons makes a go of stealing Mann away from her charming doofus of a husband (Eric Bana), and much of that time is eaten up with an endless procession of needless comedian cameos.

At 90 minutes or even two hours, this would be a lean movie with enough sting to make its harsh life lessons linger. Simmons is a tragic figure, all the more so because he willingly chose his fate and seems unwilling to take the salvation offered to him by Ira.

The key to Simmons—explored so well by Sandler, proving once again that comedians handle drama as effectively as any actor—is that, while pitiable, Simmons is not (and does not allow himself to be) sympathetic. Ira, bless him, never stops trying. It’s Ira’s little bit of grace that gives Funny People one of its few lasting merits.