A Note of Appreciation for The Offbeat Charm of Maggie Gyllenhaal

The actress escapes any straightforward categorization.

Kindergarten Teacher

Maggie Gyllenhaal has never been interested in simplistic characters. When she won the Golden Globe for Best Actress in a Miniseries in 2016 for The Honorable Woman, she declared that it is not enough to simply make movies about women but to instead make room for “women who are sometimes powerful and sometimes not, sometimes sexy, sometimes not, sometimes honorable, sometimes not.”

Common themes such as vulnerability, sexuality, and an embrace of complexity run throughout her work, yet each of her characters feels completely unique. Gyllenhaal’s recent work as Lisa in The Kindergarten Teacher and as Candy in The Deuce signal her continued commitment to bringing interesting, contradictory women to life. It is more than likely that her career will continue to blossom in fascinating and unexpected ways, and these most recent performances offer an opportunity to look back over the work she has done thus far and the graceful ways she has given life to characters who are brilliantly complex.

Her performance as Candy is certainly one of the highlights of HBO’s The Deuce, which finished its second season last November. Since the beginning of the series, Candy has retained strength and intelligence, characteristics that help her survive the mean streets of 1970s New York City, particularly within the unforgiving sex work industry. Candy’s curiosity and genuine interest in pornographic filmmaking propel her off the dirty city streets and into the director’s chair. She stands firm in her desires, even when faced with constant sexism and objectification. Many people in the adult film industry refuse to take her seriously and attempt to box her in as a performer, but she never lets go of her desire to run the show.

Candy has a keen eye for what looks good on camera and has a special knack for turning on her actors so they give authentic (and therefore hotter) performances. One of the most memorable scenes in the series comes in the season one episode “Au Reservoir,” when she takes the reigns on one of Harvey’s productions when Lori is having trouble expressing any kind of emotion on screen. Candy compliments Lori’s body, softly reassuring her how good she looks, urging the performers to switch positions so the camera can pick up their movements better. Her words bring Lori to sexual bliss, transforming the uninspired scene into something magical and erotic. Candy’s artistic talent and power (economically, creatively) have only continued to grow throughout the series, and there is no doubt that by season three she will be running her own pornographic empire.

Even toward the beginning of her career, the roles she appeared in were memorable, even if she was only on screen for a short period of time. Her roles as Raven the Satanist in Cecil B. Demented (2000) and as Elizabeth in Donnie Darko (2001) demonstrate her sharp intelligence and ability to play women who are simultaneously sweet and edgy. But it was not until her performance as Lee Holloway in Secretary (2002) that she was truly able to demonstrate her full range of talents. Gyllenhaal portrays Lee as a vulnerable woman holding more pain inside than she knows what to do with. In fact, she is a habitual self-harmer, cutting and burning herself when confronted with the profound anxiety of living in a seemingly normal suburban home that harbors secrets of abuse and drunkenness.

Lee experiences a confidence boost when she is hired as a secretary to lawyer E. Edward Grey, her quiet giddiness on display as she practices her phone manners while submerged in a bubble bath at home. Her performance as Lee is exquisitely nuanced, as she slowly discovers how to channel her pain into a consensual, mutually pleasurable BDSM relationship with Mr. Grey (no, not THAT Mr. Grey). Gyllenhaal brings Lee to life with small affectations such as sticking her tongue out while typing, nervously giggling, and whispering pleasurable phrases to herself (“four… peas!”).

Gyllenhaal and Spader, in the role of Edward, play beautifully off one another as their characters build a deeply satisfying emotional and sexual relationship, one in which they fall naturally into the positions of dominant and submissive. As this relationship blossoms, so does Lee — Gyllenhaal understands the deep power Lee derives from getting in touch with her submissiveness. In the end, she defiantly leaves behind all of the things that drag her down, including her well-meaning but boring boyfriend, vanilla sex, self-harm, and her screwed-up parents, and pursues 24/7 dom/sub marital bliss with Edward. Lee is one of many starring roles in which Gyllenhaal embodies a character who feels just as real, vulnerable, and complex as any non-fictional woman.

After Secretary, Gyllenhaal took parts in an array of films, from the delightful Mona Lisa Smile (2003) to Criminal (2004) and Trust the Man (2005). Perhaps one of her most underrated performances is as Sherry Swanson in Laurie Collyer’s Sherrybaby (2006). Gyllenhaal gives a devastating performance as Sherry, a former heroin addict who has just been released from prison and is working hard to get her life back together. Sherry is at times childish and whiny, at other times aggressive and violent, but most of the time she is brimming with a determination that borders on clueless desperation. She has a jarring ability to seduce whomever she wants and is keenly aware that she can use her sexuality to get what she wants. Even if what she wants is, well, to get properly laid.

In a 2018 interview for Vulture, Gyllenhaal notes that she is “not interested in showing the wish of what it looks like to be human,” but that she would rather show what life actually looks and feels like. Life can be difficult and messy, sometimes as horrifying as having nowhere to live and not being able to take care of your child. Gyllenhaal does not shy away from any of the ugliness that pervades Sherry’s life, whether it be a relapse, a fight with a woman in her halfway house, or sobbing in her father’s arms while he molests her. Yet that is not all there is to this story, and Gyllenhaal is attuned to the full range of experiences and emotions, both good and bad. Sherry has some bright moments of laughter, kinship with her friend/lover Dean, and sweetness when she gets to spend time with her daughter. Life is never all good or all bad for people, and Gyllenhaal brings this truth to light in many of her performances, exemplified by Sherrybaby.

In a recent interview for Harper’s Bazaar UK entitled “Life Lessons with Maggie Gyllenhaal,” she notes that she is energized by roles that feel slightly dangerous, roles that require her to take some risks. As she observes, her performance as Lisa in The Kindergarten Teacher is a perfect example of a risky, surprising role that allows her to demonstrate darker, less glamorous desires and emotions. Sara Colangelo’s feature is a reworking of a 2014 Israeli film of the same name directed by Nadav Lapid. It tells the story of a dissatisfied primary school teacher who grows increasingly obsessed with one of her students, a little boy with a stunning knack for poetry.

What makes this performance so special is the way Gyllenhaal slowly unravels, moving from an initial innocent curiosity and desire to support little Jimmy to an inappropriate, boundary-breaking obsession. She urges Jimmy’s father, Nikhil to fire Jimmy’s current babysitter, Becca, and offers to babysit him every day after school — indeed a strange request from a kindergarten teacher. Without anyone’s knowledge, she takes Jimmy to a poetry reading, propping him up onstage to recite his beautiful lines, which she had until that point been presenting to her poetry class as her own.

Lisa begins to buzz with nervous, desperate energy, an energy she was seemingly able to keep hidden beneath the surface in her professional and family life until she discovers Jimmy’s strange talent. Nikhil angrily transfers Jimmy to a new school following this incident, and Lisa promptly shows up at his kindergarten class and lures him away to a northern cottage, where she tells him she plans on taking him across the border to Canada. There is something unshakably sweet and gentle about Lisa, yet Gyllenhaal never lets us forget the strange darkness that resides on the edges of her smiling face.

Jimmy is perpetually calm, with his head in the clouds, but it is remarkably painful when he locks Lisa in the bathroom and calls the police, declaring that he knows for a fact he has been kidnapped. Lisa breaks down, crumbling and desperately trying to get Jimmy to understand that nobody understands his talent like she does. Her tenderness shines through as she gives Jimmy the information he needs to lead the police to his whereabouts. Maggie Gyllenhaal is uninterested in playing black-and-white, one-dimensional characters, instead favoring complicated, strange, deeply hurt people who retain a sense of humor and sweetness.

In the Vulture interview, Gyllenhaal mentions that she wants to try her hand at directing films and that as a woman who loves movies and storytelling, she grew up being told the best way to express that love was through acting. Now she is realizing that she has every right to want to take creative control and direct the stories that speak to her. One can only imagine that a sensitive, thoughtful, and intelligent woman like Maggie Gyllenhaal will make a fantastic director, seeing as she has been bringing widely varied stories to life for over two decades now through her brilliant characterizations. Wherever she ends up, it will surely be as exciting and electrifying as any of the performances she has given so far.

Actual film school graduate. Perpetually sleepy.