Gyllenhaal's parents, Stephen Gyllenhaal (a movie and TV director) and Naomi Foner (a screenwriter), move the family from their native New York to L.A., where Gyllenhaal and younger brother Jake attend Harvard-Westlake School. She acts in school theater productions at the private prep academy. "Even in elementary school, I took it really seriously," she tells The Guardian in 2003. "I was always doing plays."
Gyllenhaal makes her film debut in her father's drama Waterland. It is the first of six films directed by him (pictured with Maggie, Jake and Naomi) in which she appears. But auditioning outside of the family circle proved to be difficult for the unconventional beauty. "For so long I was told I wasn't sexy enough or beautiful enough," she tells Entertainment Weekly in 2006. "It felt confusing and painful."
After graduating from Columbia University with a degree in Eastern religions and literature, Gyllenhaal appears in her brother Jake's star-making vehicle, Donnie Darko. The cult hit opens with their characters yelling at each other over a family dinner. Gyllenhaal tells The Times that it was difficult to watch her younger brother (left) become a star while she struggled with her career.
At a dinner party, Gyllenhaal meets Peter Sarsgaard (right), and the two actors begin dating. Although the couple remains discreet about their relationship, she tells the AP in 2007 that she would love to make a 1940s style romance film with him – something like the Hepburn-Tracy movie Desk Set.
Secretary (left) finds Gyllenhaal in an sadomasochistic love story with James Spader. "Secretary was mind-blowing," she tells the Austin American-Statesman. "It was the first time that I sort of had a whole meal in a role as opposed to just a tiny bit." Director Steven Shainberg tells EW, "Maggie is this tremendously intelligent and alive and funny actor...It's particularly hard when you're not, you know, Kate Bosworth…Maggie doesn't look like that and isn't like that." Her performance earns her Golden Globe and Independent Spirit Award nominations.
The newly in-demand actor appears with Meryl Streep in Adaptation and in George Clooney's Confessions of a Dangerous Mind. She also nabs her first commercially successful film, Mona Lisa Smile. The 1950s drama costarring Julia Roberts and Kirsten Dunst – whom she'll later introduce to Jake – grosses $141 million worldwide. Gyllenhaal (pictured with costar Ginnifer Goodwin) plays a promiscuous student at a women's college.
While promoting her movie The Great New Wonderful about post-9/11 New York, Gyllenhaal says, "I think what's good about the movie is that it deals with 9/11 in such a subtle, open, open way that I think it allows it to be more complicated...because I think America has done reprehensible things and is responsible in some way." Her comments bring a slew of negative press, but she stands by them in a follow-up statement. She later spends time with Port Authority officer Will Jimeno and his wife, Allison, whom she portrays in Oliver Stone's World Trade Center (pictured with costar Michael Peña).
Gyllenhaal plays a drifter who manipulates and sleeps with both a closeted gay son and his father in Happy Endings (pictured with costars Jason Ritter and Tom Arnold). "I kind of believed when I was shooting that movie that she was almost like an angel," she tells public radio program Fresh Air. "And I kind of believed that she was really helping them, and she does really help them." The New York Observer describes her as "marvelously gifted and scrumptious" in this film.
Gyllenhaal, 28, and Sarsgaard, 35, announce their engagement and Gyllenhaal's pregnant. "He's so excited about the baby," she tells Marie Claire. But the baby won't hinder any wedding plans. "We don't want to just go to City Hall," she adds. "I want the fairy tale. I've had many different incarnations of my fantasy wedding dress." In October, they welcome a baby girl named Ramona. Uncle Jake tells PEOPLE of having a niece, "It's great, wonderful...She's not talking yet, but she looks amazing. I revel in her growth. It's an amazing process to watch – and to watch my sister also."
Gyllenhaal appears on the cover of Marie Claire, where it's clear that her 9/11 controversy is still on her mind. "Once I got over the pain of people being mad at me and not liking me," she says, "what I was most sad about was that, all of a sudden I was given this huge forum. And I wasn't able to articulate what I wanted to say. It was an incredible lesson." That month, she stars in Trust the Man with Billy Crudup, and falls for Will Ferrell in Stranger than Fiction. The Hollywood Reporter deems her "especially sexy here."
BIOGRAPHY (top to bottom): Larry Busacca/WireImage; Jeff Vespa/WireImage; Dimitrios Kambouris/WireImage; Kobal Collection/Wireimage; Everett Collection; Everett Collection; New Line; Humberto Carreno/Startraks