9. Ashton Kutcher - The Butterfly Effect
Much like Culkin, comedy goofball and venture capitalist Ashton Kutcher tried his hand and getting dark and gritty in the awful 2004 thriller The Butterfly Effect. The convoluted, overwrought sci-fi thriller sees Kutcher's Evan Treborn discovering he has the ability to travel back in time into his younger self and alter events of the past in order to improve the present for him and his friends - with grim consequences.
The Butterfly Effect, for all it could have been an entertaining sci-fi B-movie, frequently fails to understand its own rules and is so full of morbid and distasteful subplots that instead made the film feel creepy and depressing. Kutcher himself felt out of place in the lead role, constantly falling back on the look of gormless confusion that defined his bumbling characters in That '70s Show and Dude, Where's My Car?
He certainly wasn't the reason for the film's failure, as every facet of The Butterfly Effect was sloppy, inconsistent and unappealing. Stick to capitalism, Ashton. It won't endear you to anyone but at least you're quite good at it.