Maggie Gyllenhaal has been acting since the 90s, and the majority of her on-screen performances have been nothing short of spectacular. She was born into the film industry as her father, Stephen Gyllenhaal, is a director, and her mother, Naomi Foner Gyllenhaal, is a screenwriter and director. Today, Maggie and her brother Jake are considered two of the best actors of their generation. She can carry a film, and she is able to generate palpable chemistry with her on-screen counterparts. From playing the Caped Crusader's doomed love interest in legendary director Christopher Nolan's The Dark Knight to a Staten Island kindergarten teacher in 2018's The Kindergarten Teacher, and even a kinky yet awkward secretary alongside James Spader in Secretary, Maggie is undoubtedly one of her generation's most competent, diverse, multitalented actresses.
Even if the films are not, Gyllenhaal's performances are almost always met with critical acclaim. She even scored an Academy Award nomination for Best Supporting Actress in Crazy Heart, working alongside Academy Award-winning juggernaut Jeff Bridges. What's more, Gyllenhaal has moved behind the camera and is currently earning buzz with her screenwriting and directorial debut The Lost Daughter, starring the great Olivia Colman, Dakota Johnson, and Jessie Buckley. Here are our picks for Maggie Gyllenhaal's best movies.
6 Stranger Than Fiction
In Stranger Than Fiction, Maggie Gyllenhaal stars as a tax-evading baker named Ana Pascal who falls in love with Mr. Harold Crick, an auditor for the IRS played magnificently by Will Ferrell, who is having his life narrated by a British author in this dark comedy. Sounds weird? It is, and it works as Gyllenhaal delivers a brilliant performance as a rebellious free spirit, and she steals every scene in which she appears. Her screen time is limited, but she makes the most out of every second, bouncing off Will Ferrell with stellar chemistry. Her "anarchistic" view of the world changes Harold and helps prepare him to face his own death that he knows is imminent.
Gyllenhaal's performance adds emotional weight to the film. Her acting compels the audience to care for Harold as Ana does. The film is phenomenal, and Gyllenhaal may not be the lead, but her scenes are some of the most memorable. And in a film packed with talented actors and memorable performances, she shines alongside Will Ferrell, Emma Thompson, Dustin Hoffman, and Queen Latifah.
5 Donnie Darko
While Maggie takes a back seat to her brother Jake in the cult classic Donnie Darko, her performance is still memorable and worthy of this list. Maggie plays the role of the older sister to a tee. Maggie and Jake are phenomenal when they share scenes (particularly the opening dinner scene). Their chemistry seems effortless. Both Jake and Maggie would go on to reach Hollywood super stardom. This film is arguably considered the catalyst for the Gyllenhaal siblings' rise to greatness.
4 The Kindergarten Teacher
Maggie Gyllenhaal radiates in 2018's The Kindergarten Teacher, playing Lisa Spinelli, a Staten Island teacher who becomes obsessed with a student she believes to be a poetic prodigy. The obsession slowly starts to cause Lisa to unravel to the point where she kidnaps the child prodigy because he is being taken to a different school. Gyllenhaal once again shows her diverse skillset by slowly turning from concerned teacher to obsessed stalker. Throughout the film, Gyllenhaal's obsession seems almost reasonable to the audience, as Lisa continually justifies her actions as she believes she is doing what is in the child's best interest. Once again, Gyllenhall turns in a chilling yet brilliant performance earning a spot on the list.
3 Secretary
Maggie Gyllenhaal's talent is on full display in 2002's Secretary. Gyllenhaal stars as Lee Holloway, an awkward secretary who eventually becomes romantically involved with her emotionally damaged boss played masterfully by James Spader. The film delves into sadomasochism and almost seems like the inspiration for Fifty Shades of Grey. Secretary sees Ana transforms from an awkward oblivious loner to a woman who knows what she wants. Gyllenhaal's work in this film earned her a Golden Globe Nomination for Best Actress in a Comedy or Musical, and it also earned her the number three spot on our list.
2 The Dark Knight
Coming in at number two, Gyllenhaal stars as Rachel Dawes, the doomed love interest of Batman in Christopher Nolan's The Dark Knight. This role is significant for several reasons. First, The Dark Knight is widely heralded as the greatest superhero movie ever made. Second, Gyllenhaal stepped in to replace Katie Holmes, who played Rachel Dawes in Batman Begins. Many were skeptical of this change and didn't know if Gyllenhaal could hold her own with industry heavyweights like Christian Bale, Heath Ledger, Morgan Freeman, and the swath of stars included in this film. However, she put all that doubt to rest by playing off Bale and Aaron Eckhart like a pro.
1 Crazy Heart
And coming in at number one, Gyllenhaal stars alongside Jeff Bridges as Jean Craddock in Crazy Heart. Gyllenhaal shines as a journalist interviewing the has-been alcoholic country music star Otis "Bad" Blake (Bridges). The interview subsequently leads to a romantic relationship between Otis and Jean. Gyllenhaal is nothing short of perfect as she slowly helps Blake get his life back on track. Gyllenhaal and Bridges' chemistry is palpable. Their breakup and reconnection feel raw, thanks mainly to the two's fantastic on-screen chemistry. Bridges won an Academy Award for Best Actor, while Gyllenhaal walked away with a nomination for Best Supporting Actress. This is her best performance to date, but Gyllenhaal is still in the prime of her career and will undoubtedly continue to make fantastic films for us to enjoy.