2. King Louie XIV/Philippe - The Man In The Iron Mask (1998)
DiCaprio's first role after Titanic was actually playing two people, taking on the dual role of the dastardly King Louie XIV and his more heroic twin brother Philippe. Based on the works of Alexandre Dumas, it takes stories of the musketeers and churns them out into whatever this is. There's an impressive cast, with the likes of Jeremy Irons, Gerard Depardieu, and John Malkovich playing musketeers, but an air of them just phoning it in. Ironically, DiCaprio has two roles in the movie, but his presence is hardly felt at all throughout it, although it does have the weird trivia of him winning the Razzie for Worst Screen Couple as the twins.