Gyllenhaal shines in this provocative romantic comedy-drama as Lee Holloway, a young woman who takes a job as a secretary for a demanding attorney.
In this acclaimed drama, Gyllenhaal stars opposite Jeff Bridges as Jean Craddock, a journalist who forms a connection with a washed-up country music singer.
Gyllenhaal delivers a powerful performance as Sherry Swanson, a young woman struggling to rebuild her life after serving time in prison.
Gyllenhaal plays Ana Pascal, a quirky baker who becomes entangled in the life of an IRS auditor who discovers he is a character in a novel.
Gyllenhaal joins the cast of Christopher Nolan's acclaimed Batman trilogy as Rachel Dawes, a Gotham City district attorney and childhood friend of Bruce Wayne.
In this mind-bending comedy-drama directed by Spike Jonze, Gyllenhaal portrays Caroline Cunningham, the object of the protagonist's infatuation.
Gyllenhaal takes on a supporting role in this offbeat comedy-drama as Clara, a member of an eccentric experimental rock band led by the enigmatic Frank.
In this historical romantic comedy, Gyllenhaal plays Charlotte Dalrymple, a progressive-minded social activist who challenges the conventions of Victorian society.
Gyllenhaal has a memorable cameo in this indie comedy-drama as LN, a self-absorbed new age mother who clashes with the film's main characters during a brief encounter.
Gyllenhaal joins an ensemble cast in this period drama set in the 1950s, portraying Giselle Levy, a free-spirited student at Wellesley College who befriends the film's protagonist, played by Julia Roberts.