You'll notice that the trailers for Funny People have been careful to remind you that this is the "third film from Judd Apatow," which is meant to make you realize that he is actually solely responsible for only two very funny, very consistent comedies (40 Year Old Virgin and Knocked Up) and can't necessarily be blamed for all the other products he's lent his name and a few jokes to, leading many people to rebel against him and his repertory company (understandable, I guess, although I insist that most of the inferior Apatow-brand is still better than the average studio comedy). Apatow is a sharp writer, and I'm certain he could crank out a few more Virgins with relative ease, but his third film is a bid for something more, a transition work to show that he can write a well-observed character piece that trades in real emotion and never turns to elaborate set pieces for a laugh (no chest waxing scenes or graphic births). For the fans, he proved that from the start (Freaks and Geeks, folks!), but for his first big-screen "dramedy" the (often too apparent) influence seems to be the James L. Brooks of Terms of Endearment and Broadcast News. This film isn't in that league, but a surprising amount of it works.
The first image of the film is of a young Sandler making prank phone calls, and the footage is reportedly actual video shot by a young Apatow when the two roomed together in their early years (the autobiographical element of the film is interesting, with Sandler playing a very Sandler-esque character which seems to also be a version of young Apatow...not to mention the--usual--casting of Apatow's own wife and children and, this time, parents!). We then cut to the present, with Sandler playing George Simmons, a former stand-up comic who has squandered his talent in brainless mainstream comedies that consist mostly of making funny voices (such as Re-Do, where Sandler's adult face appears on the body of a baby). After receiving a seeming death sentence of leukemia, Simmons returns to his stand-up roots which results in a bizarre routine of self-loathing and audience baiting and leads him to hire an up-and-coming comic, Ira (Seth Rogen) as a new jokewriter and personal assistant. Ira sees Simmons as a useful leg-up in the business. In fact, everyone in the film is using each other (the most traditional Apatowian moments occur in the banter between Ira and his fellow comics and roommates, played by Jonah Hill and Jason Schwartzman, the latter especially funny as the new star of an absolutely insipid sitcom called "Yo, Teach" who is prone to stealing girls from his friends by giving them ten days to seal the deal: "Don't back me into a corner and make me fuck my way out.").
As the trailers reveal, the film is less about Simmons' battle with leukemia and more about the idea of what one does when granted a new lease on life. That sounds sappy (and Apatow in interviews unhelpfully describes the film as one about "second chances"), but the film is actually up to something darker. The rejuvenated Sandler seeks a reconcilation with his ex-wife but soon reverts to being the same old dick he was before. The film goes pretty badly astray in this long section near the end, including a "chase the girl to the airport" scene which I think is meant to cleverly tweak that stale convention but plays more like a concession to the mainstream). But the final implications and scenes recover to say something interesting about Simmons and comedy in general. Putting aside his usual selfishness, if only for a moment, Simmons reaches out to help improve Ira's comedy, telling him that his work can only succeed if it's a reflection of his real self and not just what he thinks the audience wants to hear, something that Simmons (and perhaps Sandler himself for most of his career?) has never managed to achieve. Apatow is striving to achieve it himself here. His "third film" is not his "best," but it's probably the most honest.