With Funny People, the Adam Sandler persona is subjected to careful dissection and revealed at last as a self-obsessed asshole whose childlike whimsy and offhand charm can no longer make up for a lack of regard for anything outside of his limited worldview. Not that earlier incarnations of Sandler's eternal adolescent weren't equally myopic, but what was amusing at 29 becomes pathetic at 43, and while a film such as Billy Madison charts an eventual, if belated, entry into manhood for its hero, Judd Apatow's reflexive, cock-obsessed picture, which takes its lead actor's persona as its central subject, posits Sandler's infantilism as something like an eternal condition.
Apatow wasn't the first filmmaker to re-contextualize the Sandler character (Paul Thomas Anderson got there seven years earlier), but he brings his meta concerns front and center by casting the actor as a version of himself—in other words, an idle, exorbitantly wealthy actor who made his fame and fortune starring in a series of asinine comic pictures that even he knows aren't any good. Simultaneously building up and parodying the real-life context, Apatow creates a rich, self-referential world around his character, loading the film with inside-but-not-too-inside quips (Sandler's character's agent tells him that Paul Rudd "wants to do a bromance" with him), countless celebrity cameos (Eminem, Sarah Silverman, a foul-mouthed James Taylor), and takeoffs on the sort of films that made the actor famous (titles include Merman and My Best Friend Is a Robot).
Sandler stars as George Simmons, the aforementioned comic actor, whose routine of wallowing in his own loneliness is interrupted when his doctor informs him that he's dying of a rare form of leukemia. Returning to the stand-up scene for a round of self-pitying monologues, he befriends Ira Wright (Seth Rogen), a struggling young comic who's hired ostensibly to write jokes for him and serve as his personal assistant but actually to keep him company and listen to his obsessive, pathological jokes about dick size. Wright's eager earnestness complements Simmons's worldly cynicism and the two seem to strike up a fast friendship, but with Sandler's character, there's always the sense that people are ultimately dispensable and whenever the two get in an argument, Simmons is quick to remind Wright that he's a mere "assistant" subject to his personal whims and not an actual friend.
Still, at the film's halfway point, the narrative seems poised to follow the same trajectory as Simmons's hit film Re-do, in which, transformed into a toddler, he comes to a greater self-understanding, or as a character puts it—in a phrase that might describe the progression of most of Sandler's output—"it takes being a baby to learn how to be a man." Simmons begins reconnecting with his estranged family and generally trying to put things right until—spoilers herein—a visit to the doctor's reveals that the experimental medication he's been taking has been entirely successful and that he is no longer sick. From here the film shifts dramatically, with most of the second half revolving around an extended set piece in which Simmons and Wright pay a visit to the former's ex-fiancée in Marin County while her husband is away on business.
As Wright distracts her two young daughters, Simmons makes a successful play for his ex, Laura (Leslie Mann), and the two end up planning a new life together—until the unexpected arrival of the husband (a boorish and very funny Eric Bana) complicates the matter. Although this lengthy sequence fails to sustain the same dramatic interest as the film's first half, it serves as a testing ground for the Sandler character faced with a morally ambiguous situation. While Simmons thinks he's doing everyone a favor by freeing Laura from a troubled marriage, the film makes clear that he's really just breaking up a family out of his own selfish interest in reconnecting with his ex, the matter clinched when he finds her daughter's rendition of "Memory" from Cats to be humorous rather than moving. Apatow's reverence for the nuclear family may be more than a little off-putting, but it's clear that, for Laura, life with Simmons would not be appreciably different than life with her philandering husband and, by the end of the sequence, our hero has managed to alienate not only his ex-fiancée but his only friend as well.
As the Knocked Up auteur presents him, the Sandler character is capable of occasional kindnesses, but is unable to sustain a genuine, unselfish interest in another human being. Even when he reconciles with Wright at the film's conclusion, we understand that it's just a matter of time before he winds up insulting him again and retreats back into his self-fabricated isolation. Well into his 40s, Sandler may still be stuck portraying the same arrested adolescent he created some 15 years earlier, but with Funny People, he brings a welcome self-awareness to the character that he's made a career out of playing. Along the way, he gets to rip off a few good jokes, but the fact that at least half of them have to do with penis size should be a pretty good indication of the limits of the actor's persona.