When the first images of Jack and Jill began to hit the Internet, and its premise/concept became public knowledge (Adam Sandler plays two characters: one more or less based on himself, the other his twin sister), many commented that Sandler was making exactly the same movie for which he'd supposedly made fun of himself in Judd Apatow's Funny People, i.e. the fictional Merman or Re-Do. The actual Jack and Jill is far more sinister, nothing less than a feature-length actualization of the "piano man" scene from the same film, in which Sandler's George Simmons character, in a stream of smiling-aggressive invectives, makes it clear just how deeply and thoroughly he holds his audience in contempt. More bluntly than ever before (and that's saying something), Sandler uses an entire film to let his loyal fans know that he thinks they're all a bunch of stupid assholes.
When it comes to a movie like this, I don't want to get stuck in Roger Ebert mode and damn the film solely for its logic-destroying product placements, its poorly conceived verbal and sight gags, or its humiliated cast. Even (or especially) when the film passes through its lowest depths, I try to apply the idea that a movie like Jack and Jill is some kind of meta-textual commentary, something cinema studies majors can write papers on. Maybe it's an elaborate, essay-style docu-fiction about what it means to be a star in the post-9/11 digital world or, more specifically, what it means to be Adam Sandler, multimillionaire comedian, whose Happy Madison production company has, since 1999, given us countless images of the elderly getting punched in the face, animals suffering impossible CGI abuse, and celebrities from every—and I mean every—imaginable plane of existence debasing themselves in an unspeakable, Dante's Inferno-style variety of ways. And Adam Sandler spends half the movie made up as a woman, yet another connection to be fostered between him and Jerry Lewis, who appeared in full drag in many of his greatest films, like The Ladies Man and Hardly Working. (Lewis himself would likely cite Milton Berle as his inspiration, in that regard.)
The only message here, meta or otherwise, is this: People who pay to see this kind of movie are dumb suckers, and deserve a movie that treats them as such. Early on in Jack and Jill, Mexican television star Eugenio Derbez, playing Sandler's landscaper, carries around an unopened bottle of Coca-Cola for no reason whatsoever, but that's only the tip of the iceberg in a movie that's just as much about commercials and product placement as it is about its ostensible, sibling-conflict premise. Sandler's Jack is in advertising, the movie features innumerable celebrity pitch-men (Billy Blanks, Jared Fogle, John McEnroe), and the major subplot involves Jack trying to land Al Pacino for a Dunkin' Donuts ad campaign. The joke, however, is on the moviemakers as much as it's on us: Pacino rapping (rapping!) in a TV spot for corporate cappuccino, when you get down to cases, is indivisible from Pacino agreeing to be in this movie. It could be said that that's the point, but it's a point that only goes to highlight the difference between a film that hates only its audience and one that hates itself too.
There really isn't much more to say. The movie begins with an Apatow-like double-prologue (first, real-life twins talk about being twins, then fake home movies show Jack and Jill as kids), which can be interpreted either as a salute to the Freaks and Geeks creator, or just Sandler wiping his ass again. Katie Holmes appears, though the way she's treated like a porcelain doll packaged in an ocean of Styrofoam leads one to suspect Tom Cruise was watching every single frame of her involvement. Shot on the relatively new Arri Alexa, the same digital camera that was used for Melancholia and Drive, Jack and Jill looks at least as crisp as any promos the main character might have made himself, if such praise can be lavished upon such a slapdash production, much of which appears to have used the first take every time. If the result is a movie that seems like a much slicker, more condensed, and speedier version of the Sandler comedies that have guaranteed his grandkids' retirement, count it as a blessing that it's over quickly. Not without pain, but quickly.