2001
2001In the early aughts, the actors we've come to consider A-Listers began their breakthroughs with films at Sundance. At just 20 years old, total heartthrob Jake Gyllenhaal premiered the off-kilter Donnie Darko with director Richard Kelly. [Richard Kelly, Jake Gyllenhaal, 2001 via] Jake's big sis (and Donnie Darko co-star) Maggie was also on hand to promote the film. [Maggie Gyllenhaal, Jake Gyllenhaal, 2001 via]