9) Donnie Darko
Some of the best movie experiences happen when movies are able to pull off starting out as one type of film and then turning into something completely different and unexpected and crazy. One of the most memorable examples of this in recent memory is The Cabin in the Woods, which turned the horror genre on its head to great effect. Richard Kelly’s debut feature Donnie Darko is similarly a seemingly ordinary teenage angst-filled coming of age story until a bizarre twist turns it into something else entirely.
The film works as both a teenage rebellion story and an apocalyptic, Take Shelter-like story of a person with information via premonition of sorts that the world is about to end. It would seem like a John Hughes movie if Molly Ringwald had ever been visited by a creepy looking rabbit who told her to burn things. It has its share of WTF elements involving space and time but this might be the sweetest movie on this list, in no small part due to the work of a young Jake Gyllenhaal and the character of Donnie as this troubled but endearing kid.