Sandler plays Barry Egan, a schnook who runs an absurd business somewhere in the San Fernando Valley (Anderson's favorite turf). The company seems to specialize in novelty toilet plungers for hotels and motels...or something like that. Even if the product were more sellable, it's doubtful that Barry's company would be doing very well: the staff, except for maybe right-hand man Lance (Luis Guzman), is completely inept... almost as inept as Barry himself.
But "schnook" doesn't really do Barry justice. Most of Sandler's characters have been schnooks of one kind or another. Barry is beyond "schnook": He's actually deeply disturbed in ways that are not at all funny.
In fact, Barry seems at least as weird as Sy the Photo Guy, Robin Williams's psycho character in One Hour Photo. He doesn't know how to relax with people. He's presumably never touched a girl. The awkwardness of his relationship to the rest of the world suggests actual organic brain damage or maybe Asperger's Syndrome, a less severe autism-like disorder. In fact, Barry is at times reminiscent of Dustin Hoffman in Rain Man.
We are given some hints of possible psychological roots for his behavior: His seven sisters love him but they all treated him with utter insensitivity when they were young. In fact, they still do. His frustration over this is such that his day-to-day, relatively composed manner is really a tissue-thin mask over a pool of seething fury.
Three events occur almost simultaneously that together push Barry to a new level. He hatches a scheme to amass frequent flyer miles by buying hundreds of containers of pudding. His sister Elizabeth (Mary Lynn Rajskub) tries to fix him up with her friend Lena (Emily Watson). And, worst of all, an idle lie about his business success makes a gang of imbecilic thugs (led by Anderson regular Philip Seymour Hoffman) assume he's worth blackmailing.
All three of these developments grind down that thin facade of control that allows Barry to function in an even marginally normal way. As he grows more confused, he erupts in episodes of frightening violence. In short, Punch-Drunk Love is obviously not targeted to the same audience as Happy Gilmore and The Waterboy.
When a director says that he wrote the script specifically for a certain actor, it's usually sheer prevarication; no one on a promotional tour is going say, "We were reasonably happy to get him, since he was our fourth choice for the role." But in this case, Anderson's claim to that effect is undoubtedly true. The film is, at its very heart, a riff or meditation on Sandler's screen persona.
Fifteen years ago, Jonathan Demme's Something Wild asked the intriguing question, "What if you took the typical screwball comedy heroine, that incredibly lovable character played best by Carole Lombard or Katharine Hepburn in the thirties, and put her in the real world? More terrifying than lovable, don'cha think?" Punch-Drunk Love does the equivalent for Canteen Boy and all of Sandler's other geek characters; it shows how unfunny -- in fact, how very scary and disturbing -- they are, if you take them out of the realm of broad comedy.
As a result, Sandler is terrific here. Down the line, he may or may not prove himself to have any range in straight drama, but Anderson has crafted the serious Adam Sandler role. It's simply impossible to imagine anyone else in the part.
Anderson gives us the appearance of a satisfying, resolved ending, but only if we don't think about what would happen to the characters if they were to keep living beyond the closing credits. There is a love scene about three-quarters through that bodes horribly ill for Barry and Lena, even while it pretends to be cute. Beneath its happy surface, it's truly unsettling... which could be said about the entirety of this strange and amazing piece of work.