For actress Maggie Gyllenhaal, entertainment is a family business - her father is director, her mother is a screenwriter, and her brother, Jake Gyllenhaal, is also an actor. In fact, her first three films (1992's Waterland, 1993's A Dangerous Woman, and 1998's Homegrown) were all directed by her father, and her brother also appeared in the last two. After graduating from Columbia University, she costarred with Jake again, playing his sister in the 2001 movie Donnie Darko.

Gyllenhaal's breakout role came in 2002, when she starred in the black comedy Secretary alongside James Spader. For her performance, she won the Best Breakthrough Performance by an Actress award from the National Board of Review of Motion Pictures, and was nominated for a Golden Globe and an Independent Spirit Award. She earned her second Golden Globe nomination for the 2006 film Sherrybaby. Other notable film roles of the 2000s include Confessions of a Dangerous Mind and Mona Lisa Smile, both costarring Julia Roberts, as well as Stranger Than Fiction, and The Dark Knight. She received her first Academy Award nomination for 2009's Crazy Heart, costarring Jeff Bridges.

In 2014, Gyllenhaal starred in the acclaimed BBC mini-series The Honourable Woman. She won a Golden Globe for Best Actress - Miniseries or Television Film for playing the title role of Anglo-Israeli businesswoman Nessa Stein, and was also nominated for a Screen Actor's Guild Award and a Critic's Choice Award. The series appeared on the year-end top 10 lists of several publications, including The Hollywood Reporter, the Los Angeles Times, and The Wall Street Journal, and won a 2014 Peabody Award.  

Gyllenhaal also has an extensive theater career. She made her stage debut in a 2000 Berkeley Repertory Theatre production of Closer, and next appeared in a Los Angeles production of Tony Kushner's Homebody/Kabul in 2004. She appeared in the off-Broadway plays Uncle Vanya in 2009 and Three Sisters in 2011. In 2014, Gyllenhaal made her Broadway debut in the play The Real Thing.