From her breakthrough role in Secretary, wearing stilettos, a pencil skirt and manacles and attempting to operate a stapler with her chin, to her directorial debut which digs into the messy truths about motherhood, Maggie Gyllenhaal has always been attracted to what she has described as “troubled women. The ones that are a real challenge. They really need me.”
It’s a quote that really gets to the heart of what distinguishes Gyllenhaal. An Oscar-nominated actor, and now — with her Elena Ferrante adaptation The Lost Daughter — an award-winning screenwriter and director, she is drawn to the kind of women whose stories don’t usually get told. She delves into the uncomfortable angles and sharp edges of her characters and found her niche by not quite fitting into the mould.
The mold — that cookie-cutter starlet formula — was particularly entrenched when Gyllenhaal was starting out in the late 90s. And her beauty — the heart-shaped face dominated by huge ice-blue eyes, the slightly melancholy downward slant to the lips — has always felt as though it was transposed from another time. You could imagine her as a contemporary of Mary Pickford in the era of silent cinema.
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The industry fretted that she was not conventionally “hot” enough, a criticism that Gyllenhaal brazened out at the time, but which she later conceded was “a hard thing to hear.” And when it wasn’t trying to maneuver her into a sexpot persona, Hollywood was instead dismissing her as “quirky” — a description she firmly rejected, stating that: “Describing someone as quirky is a way of erasing them.”
Perhaps the fact that Gyllenhaal’s first major role was as Lee, the submissive office worker in Steven Shainberg’s BDSM romance Secretary, added to the industry’s confusion as to where exactly she fitted into the somewhat homogenized mainstream movie landscape. She brought an apple-cheeked sweetness to the film’s transgressive themes, a forceful emotional intelligence which diffused any potential charges of prurience that the picture might have otherwise attracted. Consequently, she threatened to blow a gasket in the Hollywood production line.
Director Laurie Collyer, who cast her as an ex-con drug user and mother in the gritty drama Sherrybaby, realized early on that one of Gyllenhaal’s major strengths as an actor was the very thing that set her apart from many of her contemporaries. In an interview to promote the release of the film, she explained: “I think celebrity culture breeds conformity and Maggie is truly nonconformist, truly finding her own way. Even just the way she dresses — I know it sounds really superficial, but it all represents something: she’s her own person.”
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Gyllenhaal was born into the movie industry, but her upbringing didn’t fit the template of the second-generation Hollywood brat. Born in New York on Nov. 16 1977, Margalit Ruth Gyllenhaal is the older sister of the actor Jake Gyllenhaal, and the daughter of director Stephen Gyllenhaal (Paris Trout, Family of Spies) and screenwriter and director Naomi Foner Gyllenhaal (Losing Isaiah, Bee Season, Running on Empty). She only discovered that her first name was Margalit — a nod to her mother’s Jewish heritage — rather than Maggie when she asked for her birth certificate in order to take her husband Peter Sarsgaard’s name.
She has jokingly described her parents as being somewhere to the left of Trotsky but credited them with engendering in her the political engagement which has been core to her identity. She has always maintained that, “being politically active is incredibly important to me. My parents have been politicized and radical throughout my life — they taught me that I’m a part of a global community and it’s partly my responsibility to fight for what’s right.”
Gyllenhaal’s political activities range from driving voters to the polling station in Florida, speaking out in support of the jailed whistleblower Chelsea Manning and hosting a benefit for Pussy Riot.
More controversially, in 2005 she took aim at US foreign policy, suggesting that the US “is responsible in some way” for the 9/11 terror attacks. Subsequently, a Maggie Gyllenhaal fan-run Web site had to close comments after it was bombarded with criticism. Gyllenhaal at first doubled down, saying that “not to have the courage to ask these questions is to betray the victims of 9/11.” But later she acknowledged: “I regret what I said, but I think my intentions were good. Neither the red carpet nor an interview about a movie is the right place to talk about my politics.”
Another key lesson learned from her parents was that of the vagaries of a movie industry in which “you can be on top of the world and then the next year you can be nowhere. And then, later, you’re interesting again; and then, suddenly, you’re not. I watched that happen to them, and I watched it hurt them. I think I’m a bit armed by having seen that.”
It’s a pragmatic approach which has enabled her to be unfazed, though slightly irked, by questions assuming there is a sibling rivalry between her and Jake, whose career took off a few years before hers did with the film Donnie Darko.
Gyllenhaal’s insider’s eye view of the way the industry works — she started out in small roles in her father’s films, and appeared as Jake’s sister in Donnie Darko — also facilitated a smart balance in her own choices, weighing high-profile blockbuster-type films, like the Julia Roberts vehicle Mona Lisa Smile and Christopher Nolan’s The Dark Knight, against more daring and challenging independent projects.
Notable examples of the latter include Frank, in which Gyllenhaal played a scaldingly ill-tempered musician opposite Michael Fassbender, who was obscured throughout within a papier mache head. And then there was The Kindergarten Teacher, a profoundly uncomfortable portrait of a woman who becomes obsessed with nurturing the poetic talent of one of her six-year-old charges. Gyllenhaal enjoyed sneaking into screenings during the film’s festival run and eavesdropping on the audience’s squirming discomfort.
What defines her as an actor, according to her friend and Honorable Woman co-star Genevieve O’Reilly, is the fact that “Maggie is naturally and confidently curious. She is unafraid to ask questions. She is a really active listener and has a gentle honesty which provokes thought and conversation.” She adds: “Maggie is someone you lean in to. You can’t help it. I think she has a quiet fire at her core that is at once warm and potent, audacious and fiercely intelligent.”
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Like much in the world today, theater has experienced major disruptions over the six years since COVID-19. The pandemic, the war in Ukraine and social media have created a new normal of geopolitical and information uncertainty, and the performing arts are not immune to these effects. “Ten years ago people wanted to come to the theater to engage with important issues, but now the Internet allows them to engage with those issues powerfully and immediately,” said Faith Tan, programming director of the Esplanade in Singapore, speaking last week in Japan. “One reaction to unpredictability has been a renewed emphasis on