1) Vince Vaughn – Psycho
Just because Vince Vaughn appears twice in this list doesn’t mean he’s the worst example of a comedy star trying his hand at serious acting. In fact, the two examples here aside, he’s been pretty solid – in Into the Wild especially, but also in Thumbsucker, Return to Paradise, and yes, even Steven Spielberg’s The Lost World, a film in which the director apparently paid more attention to his fake dinosaurs’ performances than his actors’.
But nobody – nobody – gets away from Gus Van Sant’s Psycho remake clean. And Vaughn, out of all the actors who shouldn’t have been there doing a pointless shot-for-shot remake in the first place, is the absolute worst. Playing Norman Bates with all the skill of an amateur after-school theatre player, Vaughn is so bad, you understand why he retreated almost exclusively into comedy not long after the film’s release. One can only speculate that it was the guilt of making Anthony Perkins spin in his grave that did it.