25. Celebrity (1998)
DiCaprio's fleeting appearance in Woody Allen's black-and-white ensemble comedy Celebrity is honestly the best part of the movie, stealing the show as a charismatic and hilariously self-aware movie star with arrogance to spare.
Unfortunately, that's about the best thing that can be said of Allen's miserable tale of celebrity culture, the messy aftermath of divorce, and his relationship with the movie industry. Instead of watching like a complete story with a saleable message, the film ends up feeling like a series of unfinished scenes from an Allen parody.
Still, DiCaprio, with his charming unlikability and boundless energy, makes his small role count. It's minor Allen and DiCaprio through-and-through, but it serves as a nice reminder that the actor is rarely asleep at the wheel.