Gyllenhaal's break-out role was in the black comedy, Secretary (2002), a film about two people who embark on a mutually fulfilling BDSM lifestyle. The New York Times critic Stephen Holden noted: "The role of Lee, which Maggie Gyllenhaal imbues with a restrained comic delicacy and sweetness, should make her a star. " Mick LaSalle of the San Francisco Chronicle wrote: "Maggie Gyllenhaal, as the self-destructive secretary, is enigmatic and, at moments, sympathetic. " The film received generally favorable reviews, and Gyllenhaal's performance earned her the Best Breakthrough Performance by an Actress award from the National Board of Review of Motion Pictures, her first Golden Globe nomination, and an Independent Spirit Award nomination. Secretary was Gyllenhaal's first film role which featured full frontal nudity.  Although impressed with the script, she initially had some qualms about doing the film, which she believed could deliver an anti-feminist message. Yet after carefully discussing the script with the film's director, Steven Shainberg, she agreed to join the project.  Although insisting Shainberg did not exploit her, Gyllenhaal has said she felt "scared when filming began" and that "in the wrong hands . . . even in just slightly less intelligent hands, this movie could say something really weird. " Since then, she is guarded about discussing her role in the film, saying only that "despite myself, sometimes the dynamic that you are exploring in your work spills over into your life. "
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.