3. Donnie Darko

Jake Gyllenhaal is really sought out when it comes to playing intricate characters isn’t he? While you might have known him from Brokeback Mountain, where he played alongside Heath Ledger (rest in peace), his history of complicated characters started off with Donnie Darko, where he plays a troubled teenager struggling with his weird visions. How do you cope with knowing that your world is about to end? That you’re about to die? But more importantly, how can you distinguish visions from reality? This movie surely doesn’t give clear answers, which makes it even more intriguing to watch. Oh and by the way, his sister in the movie is also his real sister!