Maggie and Jake Gyllenhaal: The Gyllenhaals have a long history of working together, going all the way back to when they were children and starred in 1993's A Dangerous Woman, which was directed by their father, Stephen Gyllenhaal. They also appeared on two episodes of Food Network's Molto Mario with their mother, Naomi Foner. But most fans of the pair probably best remember them together in 2001's Donnie Darko.
Interestingly, Maggie had to be talked into the project when the film's director, Richard Kelly, approached her after casting Jake. "Immediately, she was like, 'Richard, you're only offering this to me because I'm Jake's big sister. You should be finding the best actress for the role,'" Kelly recalled to Vox in 2017. "So she was already trying to talk me out of casting her, in a very selfless way. And I was just really impressed by that. … So I was really determined to convince her to do it after that." (Photo via Frazer Harrison/Getty Images)