After playing several smaller roles in various movies, Maggie Gyllenhaal made her big debut as a full-fledged, first-billed star in Secretary in 2002. Her sweet looks and demeanor are given complicated depth onscreen with a subtle style that enhances the characters she plays, large part or small. With the exception of a few television-movie roles, Maggie has established herself as a big-screen player, and early in her career already showed her presence taking shape. While born in Los Angeles (on November 16, 1977), Gyllenhaal resides in New York City where she settled after attending Columbia University. She earned her B.A. in English, although she had much theater experience while in college in addition to her literary focus. She also studied briefly at the Royal Academy of Dramatic Art in London.

While Maggie focused on English academically, her stage experience would lead her back to acting after graduation. As a matter of fact, the limelight is in her blood, as she is the daughter of screenwriter Naomi Foner and director Stephen Gyllenhaal, and also the sister of actor Jake Gyllenhaal. In the early '90s she made small appearances in Waterland and A Dangerous Woman, getting her feet wet in the business in which her family had established experience. Additionally, she appeared on-stage both in New York City and in London. More than a kid sister or a daddy's girl, Maggie Gyllenhaal has become a Hollywood star in her own right.

With an interesting role in Cecil B. Demented — a strange dramatic commentary on an artist's visions and psychoses, starring Stephen Dorff and Melanie Griffith — Gyllenhaal was an intelligent performer whose beguiling looks brought all the more depth to the character she played. Continuing in the genre of bizarre and mysterious dramas, she appeared in Donnie Darko (2001), starring her brother, Jake Gyllenhaal, along with Drew Barrymore and Patrick Swayze. Maggie Gyllenhaal developed an early niche of appearing in films elating an artist's tale of woe, with notably self-reflective movies that deal with making movies. While Cecil B. Demented told a director's twisted story, Adaptation (2002) presented a screenwriter's struggle to adapt a novel into a film version. Directed by Spike Jonze, Adaptation features Gyllenhaal in support of stars Nicholas Cage and Meryl Streep. Also in 2002, Gyllenhaal's first major starring role came with Secretary, a film by Steven Shainberg. In it, she brings her signature depth and charming warmth to the role of Lee, a young woman who takes a job as a secretary and winds up discovering her own sexuality through a relationship that develops in the office.