A versatile and intriguing actress, whose penetrating acting and off-kilter beauty were initially relegated to supporting roles, Maggie Gyllenhaal broke out to the forefront with the edgy S&M themed drama "Secretary." Despite this being her first starring role, she did not spend much time in the trenches, having a relatively painless decade paying dues before getting her first major role at the age of 24. Having grown up in a family of entertainment professionals, it is no surprise Gyllenhaal decided to pursue a career in acting. Her mother is successful screenwriter Naomi Foner (Oscar nominated for her 1988 screenplay for "Running on Empty," starring River Phoenix) and her father is accomplished film and television director Stephen Gyllenhaal (nominated for an Emmy for 1990 telepic "A Killing in a Small Town" and directed feature "Losing Isaiah" in 1995). Adding a healthy dose of sibling rivalry to go along with these parental expectations, her brother is successful actor Jake Gyllenhaal ("Moonlight Mile" 2002).
Gyllenhaal was born in New York City but grew up in Los Angeles where she and her brother attended the prestigious Harvard-Wakeland prep school, known as a "who's who among who's whose kids" in the Hollywood circle. Here Gyllenhaal was an excellent student and active in the drama program. At the age of 15, Gyllenhaal had her feature debut in the nostalgic drama "Waterland" (1992), directed by her father and starring Jeremy Irons and Ethan Hawke. She next had another small role in "A Dangerous Woman" (1993), also directed by her father. In 1995, Gyllenhaal moved to New York to attend Columbia University. While she was busy studying Eastern religion and literature in school, she also found the time to further her professional acting career. She appeared in two more television movies directed by her father as well as the feature "Homegrown" (1998), also written and directed by her father.
After graduating from Columbia in 1999, Gyllenhaal certainly had ample exposure to the film and television world. However, in order to really break into the business, Gyllenhaal would need a stand-out role to get her in the running for the high-profile parts. That break came in the form of her role as Raven, a Satanic make-up artist in the eccentric John Waters film "Cecil B. Demented." (2000). This gave Gyllenhaal enough recognition that she landed a string of supporting roles the following year. She played her brother's sister in the far-out sci-fi movie "Donnie Darko" (2001), appeared in "Riding in Cars with Boys" (2001) and was featured in the teen romance "40 Days and 40 Nights."
Not the kind of actress meant to lay wait in obscurity for very long, Gyllenhaal had a breakout performance with "Secretary" in 2002. Playing a timid young woman recovering from a mental breakdown who engages in a S&M relationship with her boss, Gyllenhaal brought the depth and delicacy called for in the role. The movie won the Special Jury Prize at Sundance and was promptly picked up for theatrical distribution. Gyllenhaal's indie actress, star-on-the-rise status was solidified with awards nominations—including a Golden Globe—and her next projects, Charlie Kaufman's mind-bending film-about-writing-a-film "Adaptation" (2002) and the John Sayles directed "Casa de Los Babys" (2003). She also joined fellow up-and-comers Julia Stiles and Kirsten Dunst as students of a liberal-minded instructor (Julia Roberts) at 1950s Wellesley College, nearly stealing the entertaining but routine movie as Giselle Levy, the wised-up class rebel who sleeps around and almost loses her bearings. Quickly gaining a reputation as a cerebral actress, often compared to the likes of Cate Blanchett, Emily Watson or a young Diane Keaton, Maggie Gyllenhaal has stepped out from the shadow of her parents and her brother and to shine alone in the spotlight.
The actress continued to deliver a string of unflinching, unselfconscious performances, including Sidney Lumet's harrowing HBO telepic "Strip Search" (2004), in which two parallel plotline exploring post-9/11 issues of civil liberties and personal freedoms. Gyllenhaal played an American woman detained in China on suspicion of terrorisim, forced to defend her own rights to an interrogator (Ken Leung) in a sweltering basement prison, stripped bare both physically and emotionally. After compellingly playing a hustling con artist in the otherwise middling crime drama "Criminal" (2004), Gyllenhaal turned in one her most winning performances to date in director Don Roos' seriocomic "Happy Endings" (2005). As the morally ambiguous singer Jude, who seduces a closeted gay youth (Jason Ritter) then turns her sights on his lonely, wealthy father (Tom Arnold) Gyllenhaal dazzled with her subtle, shifting behaviors, creating a compelling, fully realized character than was neither fully good or fully bad.
She next appeared in “The Great New Wonderful” (2005), an independently made drama depicting five interwoven stories told against the backdrop of an anxious, post-9/11 New York City. Gyllenhaal played the ruthless owner of a posh pastry shop who seeks to overthrow the reigning Queen of Cake (Edie Falco), but not without heavy consequences. After voicing Zee, the Goth babysitter in “Monster House” (2006), Gyllenhaal costarred in Oliver Stone’s sober and heart-wrenching look at the 9/11 terrorist attacks, “World Trade Center” (2006). Gyllenhaal portrayed Allison Jimeno, wife of a port authority officer (Michael Pena) who gets trapped beneath the rubble after the towers collapsed with his sergeant (Nicolas Cage) and spends the next twenty-four hours trying to survive while awaiting rescue. “World Trade Center” opened to generally positive reviews, but a few expressed concern that Stone’s film may have been released too soon following the horrific events. Meanwhile, Gyllenhaal had a few more films released in 2006: “Trust the Man,” a romantic comedy following the escapades of two Manhattan couples; “Sherrybaby,” an independent drama about a well-meaning, recovering drug user trying to reconnect with his estranged daughter; and “Stranger than Fiction,” a bizarre comedy about an IRS auditor (Will Ferrell) whose life is upended when he discovers a personal narrator that knows his every thought, feeling and action—including the when and where of his death.
