Gyllenhaal's breakout 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.
Impressed with the script, she initially had reservations about doing the film, which she believed could deliver an anti-feminist message.
However, 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."

Next, she had a supporting role in the comedy-drama Adaptation (2002), a film that tells the story of screenwriter Charlie Kaufman's struggle to adapt The Orchid Thief into a film.
She later appeared in the unauthorized biography Confessions of a Dangerous Mind (2002), part of an ensemble cast that included Sam Rockwell, Drew Barrymore, George Clooney, and Julia Roberts.
The movie grossed US$33 million worldwide.
That same year, she had a small role in the comedy 40 Days and 40 Nights.
In 2003, she co-starred with Julia Roberts in Mona Lisa Smile in the role of Giselle.
In an interview with The Daily Telegraph, she revealed the reason for accepting the role was "to play somebody who feels confident in herself as a sexy, beautiful woman".
The film generated mostly mixed reviews, with Manohla Dargis of the Los Angeles Times describing it as "smug and reductive".
Her next roles were in smaller independent films: Casa de los Babys (2003), is a story about six American women impatiently waiting out their lengthy residency requirements in a South American country before picking up their adoptive babies, and Criminal (2004), a remake of the Argentinian film Nine Queens, with John C. Reilly and Diego Luna.
Gyllenhaal plays an honest hotel manager forced to help her crooked brother (Reilly) by seducing one of his victims.

She starred in the HBO film Strip Search (2004), in which she portrayed an American student in China suspected of terrorism.
For her role, Gyllenhaal had to perform multiple scenes of full-frontal nudity as the film tackled issues of strip searches.
In 2004, Gyllenhaal returned to theater in a Los Angeles production of Tony Kushner's Homebody/ Kabul as Priscilla, the Homebody's daughter, who spends most of the play searching for her elusive mother in Kabul, Afghanistan.
Kushner gave her the role in Homebody/ Kabul on the strength of her performance in Closer.
Ben Brantley of The New York Times wrote: "Ms. Gyllenhaal provides the essential bridge between the parts of the play's title."
John Heilpern of The New York Observer noted that Gyllenhaal's performance was "compelling".
Finally in 2004, Gyllenhaal was invited to join the Academy of Motion Picture Arts and Sciences.
Viewed as a sex symbol, she was ranked in the "Hot 100 List" by Maxim magazine in 2004 and 2005.

Gyllenhaal's next film role was in the 2005 comedy-drama Happy Endings, in which she played an adventuress singer who seduces a young gay musician (Jason Ritter) as well as his rich father (Tom Arnold).
She recorded songs for the film's soundtrack, calling the role the "roughest
Gyllenhaal's breakout 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. Impressed with the script, she initially had reservations about doing the film, which she believed could deliver an anti-feminist message. However, 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."
Next, she had a supporting role in the comedy-drama Adaptation (2002), a film that tells the story of screenwriter Charlie Kaufman's struggle to adapt The Orchid Thief into a film. She later appeared in the unauthorized biography Confessions of a Dangerous Mind (2002), part of an ensemble cast that included Sam Rockwell, Drew Barrymore, George Clooney, and Julia Roberts. The movie grossed US$33 million worldwide. That same year, she had a small role in the comedy 40 Days and 40 Nights. In 2003, she co-starred with Julia Roberts in Mona Lisa Smile in the role of Giselle. In an interview with The Daily Telegraph, she revealed the reason for accepting the role was "to play somebody who feels confident in herself as a sexy, beautiful woman". The film generated mostly mixed reviews, with Manohla Dargis of the Los Angeles Times describing it as "smug and reductive". Her next roles were in smaller independent films: Casa de los Babys (2003), is a story about six American women impatiently waiting out their lengthy residency requirements in a South American country before picking up their adoptive babies, and Criminal (2004), a remake of the Argentinian film Nine Queens, with John C. Reilly and Diego Luna. Gyllenhaal plays an honest hotel manager forced to help her crooked brother (Reilly) by seducing one of his victims. 
She starred in the HBO film Strip Search (2004), in which she portrayed an American student in China suspected of terrorism. For her role, Gyllenhaal had to perform multiple scenes of full-frontal nudity as the film tackled issues of strip searches. In 2004, Gyllenhaal returned to theater in a Los Angeles production of Tony Kushner's Homebody/ Kabul as Priscilla, the Homebody's daughter, who spends most of the play searching for her elusive mother in Kabul, Afghanistan. Kushner gave her the role in Homebody/ Kabul on the strength of her performance in Closer. Ben Brantley of The New York Times wrote: "Ms. Gyllenhaal provides the essential bridge between the parts of the play's title." John Heilpern of The New York Observer noted that Gyllenhaal's performance was "compelling". Finally in 2004, Gyllenhaal was invited to join the Academy of Motion Picture Arts and Sciences. Viewed as a sex symbol, she was ranked in the "Hot 100 List" by Maxim magazine in 2004 and 2005.
Gyllenhaal's next film role was in the 2005 comedy-drama Happy Endings, in which she played an adventuress singer who seduces a young gay musician (Jason Ritter) as well as his rich father (Tom Arnold). She recorded songs for the film's soundtrack, calling the role the "roughest
Maggie Gyllenhaal