She began her career as a teenager with small roles in several of her father's films, and appeared with her brother in the cult favorite Donnie Darko (2001). She received critical acclaim for her starring roles in the independent films Secretary (2002) and Sherrybaby (2006), earning Golden Globe nominations in the Comedy and Drama categories, respectively. In 2008, she received widespread recognition for playing Rachel Dawes in Christopher Nolan's superhero film The Dark Knight. Her other film credits include Adaptation. , Confessions of a Dangerous Mind (both 2002), Mona Lisa Smile (2003), Happy Endings (2005), Paris, je t'aime, World Trade Center, Monster House, Stranger Than Fiction (all 2006), and Away We Go (2009). For her performance in Crazy Heart (2009), she was nominated for the Academy Award for Best Supporting Actress. She subsequently starred in the films Nanny McPhee and the Big Bang (2010), Won't Back Down (2012), Hysteria (2011), White House Down (2013), and Frank (2014).
In 2014, she made her Broadway debut in a revival of The Real Thing , and also starred in the television BBC miniseries The Honourable Woman . For her performance in the latter she won a Golden Globe Award and was nominated for an Emmy Award .
Secretary is a 2002 erotic romance film directed by Steven Shainberg and starring Maggie Gyllenhaal as Lee Holloway and James Spader as E. Edward Grey. The film is based on a short story from Bad Behavior by Mary Gaitskill ,  and explores the relationship between a sexually dominant man and his submissive secretary.
Following Jane from her childhood as an orphan in Northern England through her experience as a governess at Thornfield Hall, Charlotte Brontë's Gothic classic is an early exploration of women's independence in the mid-19th century and the pervasive societal challenges women had to endure. At Thornfield, Jane meets the complex and mysterious Mr. Rochester, with whom she shares a complicated relationship that ultimately forces her to reconcile the conflicting passions of romantic love and religious piety.