Maggie Gyllenhaal

Born in 1977, Gyllenhaal got some early screen breaks thanks to roles in such Stephen Gyllenhaal films as Waterland (1992) and Homegrown (1998). Soon graduating from Columbia University with an English degree, pretty Gyllenhaal continued to refine her acting skills on the stages of New York and London theaters in such productions as The Tempest and The Butterfly Project. Her ascent into the collective film conscience continued with a humorous turn in director John Waters' anarchic Cecil B. Demented and alongside younger brother Jake in the surreal teen fantasy Donnie Darko (2001). Soon gaining more prominent roles alongside such hot Hollywood actors as Drew Barrymore (Riding in Cars With Boys [2001]) and Josh Hartnett (40 Days and 40 Nights [2002]), Gyllenhaal would turn up later in 2002 in eccentric director Spike Jonze's sophomore effort, Adaptation.

Her supporting roles offering but a glimpse into her engagingly offbeat talent, Gyllenhaal truly came into her own with her breakthrough performance as a mentally unstable secretary in director Steven Shainberg's 2002 dark comedy Secretary. Cast opposite former '80s wonder boy James Spader, Gyllenhaal displayed a careful balance of unshielded vulnerability and mild sadomasochism as the film's troubled lead. Nominated for numerous awards including a Golden Globe and Independent Spirit for Best Actress, Secretary found the disarming actress branded the "it" girl to watch for in the coming years.

While subsequent supporting performances in such films as Confessions of a Dangerous Mind, Casa de Los Babys, and Mona Lisa Smile may not have offered fans the large dose of Gyllenhall that they sought after Secretary, audiences could see her in a starring role opposite John C. Reilly in the 2004 George Clooney/Steven Soderbergh-produced remake Criminal. Gyllenhaal kept up her status as an independent film icon in 2005 with major parts in The Great New Wonderful and earning praise for her work in Don Roos' Happy Endings where she got to show off her vocal talents performing a selection of Billy Joel songs. 2006 would be a very busy year for the actress. She co-starred in Oliver Stone's 9/11 film World Trade Center, gave an award winning performance as a drug addict in SherryBaby, played opposite Will Ferrell in the comedy Stranger Than Fiction, and lent her voice to the Steven Spielberg produced animated film Monster House. That same year she announced that she was expecting her first child with her longtime boyfriend actor Peter Sarsgaard.

In 2008, Gyllenhaal appeared in the record-breaking box-office smash sequel The Dark Knight, taking over the role played by Katie Holmes in Batman Begins. She followed that up in 2009 with a hilarious supporting turn in Away We Go as an overly-involved mother. But it was her appearance that same year in the low-key drama Crazy Heart opposite Jeff Bridges that earned her some of the best reviews of her career as well as a Best Supporting Actress nominations from the Academy.

~ Jason Buchanan