Punch-Drunk Love (2002)
Paul Thomas Anderson's furious romantic comedy is the Pluto to Sandler's filmographic solar system. You can't help but doubt it -- does it even count as an Adam Sandler movie? And yet the pieces are there: The comedian plays Barry, a novelty plunger salesman who battles his malicious sisters, a shadowy phone-sex extortionist, and the crippling effects of depression, all while falling in love with the women of his dreams. With brighter lighting and a top-40 soundtrack, it would follow in the tracks of Happy Gilmore and Big Daddy. In Anderson's hands, it's a melancholic character study that strangles Sandler's persona with his own vocal chords. The colors are dreamlike. The anger is palpable. Sandler bursts from the seams of his own fame. It's everything we want from a funnyman-gone-serious, caustically sweet and mentally unstable, an alternative mode that Sandler's hero complex would never revert to again.
Where to stream it: Amazon Prime