With his lead role in 1999's October Sky, Gyllenhaal gained notoriety in Hollywood and shortly thereafter co-starred opposite his sister, Maggie, in Donnie Darko (2001) -- for which he earned an Independent Spirit Award nod. He then conquered more dramatic parts in The Good Girl (2002), Moonlight Mile (2002) and Proof (2005).
Gyllenhaal took on big-budget action fare in the 2004 blockbuster The Day After Tomorrow. A year later, he played a gay ranch hand in Brokeback Mountain and was rewarded with an Oscar nomination for Best Supporting Actor. His later notable works include Zodiac (2007) and Love and Other Drugs, which brought Gyllenhaal a Golden Globe nod.