The sister of Jake, Gyllenhaal is an indie actress, vocal liberal, and style icon.
Born in New York to showbiz parents Stephen Gyllenhaal (a director) and Naomi Foner (a screenwriter), Gyllenhaal grew up in LA and started acting professionally at 15, getting bit parts in feature films thanks to her director dad. After graduating Columbia, she attracted attention appearing alongside her brother in 2001's Donnie Darko, but it was her breakthrough performance as a masochistic executive assistant in the pervy 2002 movie Secretary that put her on the map. Gyllenhaal has juggled the well-worn indie path with Sherrybaby, Crazy Heart, and Away We Go with a bid for more mainstream attention in Mona Lisa Smile and The Dark Knight.
Beyond the film world, she's lent her offbeat beauty to a 2004 Terry Richardson-lensed series of ads for fashion house Miu Miu, and in 2007 appeared minimally-clothed in a campaign for Agent Provocateur lingerie. She hasn't shied from political controversies by speaking out against the Iraq War and campaigning on behalf of the ACLU. Married to actor Peter Sarsgaard, the pair has a daughter, Ramona. [Image via Getty]