Maggie Gyllenhaal is having one of her most impactful years in Hollywood yet. The New York native has received critical acclaim for her directorial debut feature “The Lost Daughter,” which has ushered her into the awards race, capable of nabbing three possible nominations for directing, adapted screenplay and perhaps even best picture. In celebration of her birthday, Variety is ranking the 10 best performances of her acting career so far, which has included some that the Oscars have recognized and many that, unfortunately, have been snubbed.
Gyllenhaal’s acting career has spanned nearly three decades, after getting her start in some of her father Stephen Gyllenhaal features, “Waterland” (1992) and “A Dangerous Woman” (1993). She moved on to bring about memorable performances opposite her brother Jake Gyllenhaal in “Donnie Darko” (2001), before moving onto more challenging vehicles like “Secretary” (2002), “Sherrybaby” (2006) and “Crazy Heart” (2009), which earned her a nomination for best supporting actress at the Oscars.
She also managed to bring in some blockbuster vehicles like Rachel Dawes in “The Dark Knight” (2008) and Carol Finnerty in “White House Down” (2013). It may be surprising to not see the former included on the top 10 list, but despite the problematic writing of the character from Christopher Nolan, she’s simply been better in other outings.
“The Lost Daughter,” adapted from the Elena Ferrante novel of the same name, is a psychological drama that has Gyllenhaal assembling the talents of Oscar winner Olivia Colman (“The Favourite”), Dakota Johnson, Peter Sarsgaard, Oscar nominee Ed Harris and Emmy nominee Paul Mescal. The film debuted at the Venice and Telluride Film Festivals and will drop on Netflix on Dec. 17.
Honorable mentions: “The Dark Knight” (2008), “Happy Endings” (2005), “Confessions of a Dangerous Mind” (2002)
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Mona Lisa Smile (2003)
Image Credit: Columbia/Courtesy Everett Collection Role: Giselle Levy
Distributed by: Sony Pictures
Directed by: Mike Newell
Written by: Lawrence Konner, Mark RosenthalThe scene that proves it: “After the war, they didn’t know each other anymore…”
As the liberal and free-spirited Giselle, who talks about the divorce of her parents, this role shows the vulnerability and pain of women who are trying to adapt in a disrespectful society. While the movie’s “Dead Poets Society” rip-off concept and predictable narratives bring the overall experience down, Gyllenhaal, once again, stands out in a sprawling cast that includes Julia Roberts, Kirsten Dunst and Julia Stiles.
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Adaptation (2002)
Image Credit: Columbia/Courtesy Everett Collection Role: Caroline Cunningham
Distributed by: Sony Pictures
Directed by: Spike Jonze
Written by: Charlie Kaufman, Donald KaufmanThe scene that proves it: “See I told you he was going to like it.”
Gyllenhaal’s limited role in writer and director Spike Jonze’s sophomore effort, following “Being John Malkovich” (1999), shows how she can be the delicious sprinkle on a tasty sundae, that includes the Oscar-nominated Nicolas Cage and Meryl Streep, and an Academy Award-winning performance from Chris Cooper. Supportive wives of screenwriters are always a favorite in Hollywood.
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World Trade Center (2006)
Image Credit: Paramount/Courtesy Everett Collection Role: Allison Jimeno
Distributed by: Paramount Pictures
Directed by: Oliver Stone
Written by: Andrea BerloffThe scene that proves it: Finding out Will is alive.
There are multiple issues with the disaster drama released just five years after the September 11 attacks. Still, Gyllenhaal’s performance as the pregnant wife of Michael Peña’s Officer Will Jimeno is not one of them. She’s able to bring the aching pain of the unknown on that fateful day while balancing the yearn for the hope that was able to bring us out of that dreadful morning. Perhaps being born in New York herself, she was able to connect deeper than many of the other elements and transcend the glaring difficulties.
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Frank (2014)
Image Credit: Lorey Sebastian/Magnolia Pictures/Courtesy Everett Collection Role: Clara Wagner
Distributed by: Magnolia Pictures
Directed by: Lenny Abrahamson
Written by: Jon Ronson, Peter StraughanThe scene that proves it: Singing “Lighthouse Keeper”
Gyllenhaal has shown an affinity to either deliver complex characters before seeing them reinvented in some future movie project or working with filmmakers who are on the precipice of their own greatness. Both of these are the case with the aggressive sidekick and fellow band member to the papier-mache head-wearing Frank (played by Michael Fassbender). Under a pre-Abrahamson “Room” (2015) Oscar nom for directing, she manages to bring this quirky tale and woman to life.
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Away We Go (2009)
Image Credit: Francois Duhamel/Focus Features/Courtesy Everett Collection Role: LN
Distributed by: Focus Features
Directed by: Sam Mendes
Written by: Dave Eggers, Vendela VidaThe scene that proves it: “When I had Wolfie, I had the most enormous orgasm.”
In Sam Mendes’ small and mostly underrated comedy about a couple (played by John Krasinski and Maya Rudolph) trying to decide on where to raise their unborn child, Gyllenhaal makes the most of her time as LN (pronounced Ellen). She’s always had an apt for making the most of dinner table scenes. No one “rejects aggression” the way Maggie does.
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Crazy Heart (2009)
Image Credit: Lorey Sebastian/Fox Searchlight Pictures/Everett Collection Role: Jean Craddock
Distributed by: Fox Searchlight Pictures (now Searchlight Pictures)
Directed by: Scott Cooper
Written by: Scott CooperThe scene that proves it: “You’re gonna be out there running around, not even remembering this day.”
Sporting a twang, and going toe-to-toe with an Oscar-winning performance from Jeff Bridges, Gyllenhaal’s Jean Craddock in Scott Cooper’s “Crazy Heart” is a heartfelt, tender turn from an actress who has never shied away from the bigger, less conventional characters. The performance serves as her sole Oscar nomination for supporting actress, after getting a mid-season campaign switch from lead, eventually losing out to Mo’Nique (“Precious”).
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The Kindergarten Teacher (2018)
Image Credit: Courtesy of Sundance Film Festival Role: Lisa Spinelli
Distributed by: Netflix
Directed by: Sara Coloangelo
Written by: Sara ColangeloThe scene that proves it: “I loved it.”
After premiering at the Sundance Film Festival, Gyllenhaal’s American take on the Israeli film puts her in the producer’s chair, as well as delivering another knockout performance as a teacher who grows obsessed with one of her gifted students. Her navigation through complex and interesting characters who are flawed yet exude desperation is one of her most pertinent capacities.
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Stranger Than Fiction (2006)
Image Credit: Sony Pictures/Courtesy Everett Collection Role: Ana Pascal
Distributed by: Sony Pictures Releasing
Directed by: Marc Foster
Written by: Zach HelmThe scene that proves it: Kissing Harold during “Whole Wide World”
Gyllenhaal has always excelled at doing so much by doing so little. In Foster’s criminally underrated dramedy about an IRS agent (played magnificently by Will Ferrell in a career-best performance), she’s able to give the audience the motivation and resilience to love Harold Crick as he finds himself in a knowing world of the time of his death. You also can’t help but love her “get bent, tax man” line.
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Secretary (2002)
Image Credit: Lionsgate/Courtesy Everett Collection Role: Lee Holloway
Distributed by: Lionsgate
Directed by: Steven Shainberg
Written by: Erin Cressida Wilson, Steven ShainbergThe scene that proves it: “I’m shy”
Before there was Anastasia Steele from “Fifty Shades of Grey” (that stars Dakota Johnson, who delivers a fantastic performance in “The Lost Daughter”), we had the invention of Lee Holloway taken by the reigns of Gyllenhaal against the tricky navigation of James Spader. For her work, she received a Golden Globe nomination for lead actress in a comedy.
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Sherrybaby (2006)
Image Credit: IFC Films/Courtesy Everett Collection Role: Sherry Swanson
Distributed by: IFC Films
Directed by: Laurie Collyer
Written by: Laurie CollyerThe scene that proves it: “Want to give your Momma a kiss?”
Gyllenhaal’s visceral and riveting portrayal of a recovering heroin addict who tries to rebuild her life after a release from prison stands as her finest moment in cinema. The cringe-factor as she navigates a dinner with her family, singing “Eternal Flame,” and the revelation of her relationship with her abusive father is executed with precision and force. It’s a turn that easily should have landed her a best actress nomination, and by my estimations, the win against an albeit spectacular Helen Mirren (“The Queen”). However, she did manage a Golden Globe nomination during the respective season.