Jake Gyllenhaal has been everything from an cutie action hero (in The Day After Tomorrow) to the obsessed tracker of a serial killer (in Zodiac) to a gay cowboy (in Brokeback Mountain, for which he lassoed an Oscar nomination). In the new political thriller Rendition (pictured), also starring Reese Witherspoon, Gyllenhaal shows off his range again, this time as a CIA analyst who questions the detention and interrogation of an Egyptian-born terror suspect.

In the following gallery, see how Gyllenhaal became not only a go-to name for such Oscar-baiting roles, but also a big-screen heartthrob.