2.) “Donnie Darko” in DONNIE DARKO In what some regard as his signature role, Gyllenhaal portrays a moody teen plagued by nightmarish visions that could actually be foretelling. It’s a testament to his talents that Donnie- as well as this hybrid of a film- come across so compelling and memorable. Won an Independent Spirit nod for his breakthrough performance in what has become a cult classic.

4.) “Anthony Swofford” in JARHEAD Playing a rookie Marine recruit during the Gulf War, Gyllenhaal embodies the palpable dislocation that results from youthful nativity succumbing to bitter understanding. As his character faces an existential meltdown, Gyllenhaal carefully reminds us that the first casualty of war- any kind of war- is innocence. Won a Hollywood Film Festival Award.

6.) “Douglas Freeman” in RENDITION The film has its share of flaws but Gyllenhaal still turns in a nicely restrained performance as a morally perplexed CIA operative. Interestingly, the best moments of his work are watching him actually NOT say or do anything (see the film and you’ll understand why). Scored a Teen Choice Award nod.

08.) “Hal” in PROOF. On the surface it seems a fairly simple role; cute love interest of a conflicted college peer. But there’s more here as he reveals himself to be the protégée of the girl’s brilliant but disturbed mathematician father. Cute looking, he subtlety lets us know that under his character’s seemingly sweet-boy exterior may lie a few ulterior motives. San Diego Critics Award winner.

10.) “Homer Hickam” in OCTOBER SKY Not quite his breakthrough performance but early evidence of the fledgling great actor within. Playing a small town boy obsessed with building his own rocket, Gyllenhaal brings the perfect amount of boyish enthusiasm, charm and earnestness to a commendable family film. Revived a Young Artists Award nomination.