- 2009: Co-starred with fiance Peter Sarsgaard in the Off-Broadway revival of Anton Chekhov's "Uncle Vanya"
- 2008: Replaced Katie Holmes as Assistant District Attorney, Rachel Dawes in the second installment of the revived "Batman" series, "The Dark Knight"
- 2006: Played the wife of a rescued Port Authority officer in Oliver Stone's "World Trade Center"
- 2006: Portrayed an ex-con in the indie drama, "Sherrybaby"; received a Golden Globe nomination for Best Actress
- 2005: Played a singer in "Happy Endings"; earned an Independent Spirit Award Nomination for Best Supporting Female
- 2004: Appeared in "Criminal" with John C. Reilly and Diego Luna
- 2003: Co-Starred in "Mona Lisa Smile" with Julia Roberts and Kirsten Dunst
- 2003: Performed at the Mark Taper Forum in a production of Tony Kushner's "Homebody/ Kabul"
- 2002: Earned widespread acclaim portraying a mentally fragile woman who embarks on an Sadomasochistic relationship with her boss in the Sundance hit "Secretary"; received a Golden Globe nomination for Best Actress
- 2002: Had a supporting role in the Spike Jonze/Charlie Kaufman comedy, "Adaptation"
- 2001: Played the sister of her real-life brother in "Donnie Darko"
- 2000: Had supporting role in John Waters' "Cecil B. DeMented"
- 1998: Acted in "Homegrown"; directed by her father and also featured her brother
- 1995: Moved to New York to attend NYU
- 1992: Feature acting debut "Waterland"; directed by her father, Stephen Gyllenhaal
- 1978: Moved with family to Los Angeles




