Sarsgaard breakout role came in 1999 when he played the killer of Hilary Swank's character in Boys Don't Cry (spoiler alert!). Since then Sarsgaard's become an indie staple with roles in Center of the World, Garden State, Kinsey and An Education, but that doesn't mean he hasn't taken on some sell-out roles in blockbusters like Knight & Day and The Green Lantern. In between movie roles, he's popped up occasionally on the off-Broadway theater circuit, starring in Kingdom of Earth and Burn This. He made his Broadway debut in 2008 with The Seagull and returned to off-Broadway with Uncle Vanya.
After dating for about four years, Sarsgaard and Maggie Gyllenhaal got hitched in April 2006. In October of that year Gyllenhaal gave birth to the couple's first child, Ramona. But don't let his low-key indie star domesticity fool you: Pre-Gyllenhaal, he was known for being a ladies' man and huge jerk. Sarsgaard was involved with burlesque queen Dita von Teese until she found out that he'd cheated on her with model Shalom Harlow. The Canadian beauty later found out that he'd cheated on her, too. [Image via Getty]