Jake Gyllenhaal made his movie debut at 11 in City Slickers (1991). From the late 1990s through the early 2000s, he starred in October Sky (1999) & Donnie Darko (2001), receiving an Independent Spirit Award Best Actor nomination for the latter. He followed up w/ roles in Bubble Boy (2001), The Good Girl (2002), Moonlight Mile (2002) & The Day After Tomorrow (2004).

He made his theater debut in a revival of This Is Our Youth in London. The play was well-received & played for 8 weeks on West End. He then starred in Jarhead (2005) & Proof (2005). However, it was his performance in Brokeback Mountain (2005) that won him critical acclaim. He won the BAFTA Award for Best Actor in a Supporting Role while also being nominated for the Outstanding Performance by a Male Actor in a Supporting Role SAG Award, the Best Supporting Actor-Motion Picture Satellite Award & the Best Supporting Actor Academy Award. Afterwards, he starred in Zodiac (2007), Brothers (2009), Prince of Persia: The Sands of Time (2010) & Love & Other Drugs (2010). For Love & Other Drugs (2010), he was nominated for the Best Actor-Motion Picture Musical or Comedy Golden Globe Award.

In the 2010s, he starred in Source Code (2011), End of Watch (2012), Prisoners (2013), Nightcrawler (2014), Southpaw (2015) & Demolition (2015). For Nightcrawler (2014), he was nominated for the Best Actor in a Motion Picture Drama Golden Globe, the Outstanding Performance by a Male Actor in a Leading Role SAG & the Best Actor in a Leading Role BAFTA Award. Leading Role BAFTA Award.