Agrado, “All About My Mother” (1999)
When Aregntine nurse Manuela loses her 17-year-old son in a tragic car accident, she quits her job and journeys to Barcelona in hopes of reconnecting with the boy’s father. A longtime proponent of bringing trans identities to the big screen, Spanish filmmaker Pedro Almodóvar outdoes himself when Manuela’s travels reunite her with an old friend: The transsexual prostitute Agrado. Played with forceful wit by Antonia San Jaun, Agrado bares her soul and confidence during a monologue in which she addresses an audience about the true meaning of “authentic.” With the poise and grace of an actress on stage, Agrado brings the crowd to a rousing applause as she boldly concludes, “We must not be cheap in regards to the way we look. Because a woman is more authentic the more she looks like what she has dreamed for herself.” It’s this fearless self-confidence that makes the character’s limited screen time so memorable.
Albert Nobbs, “Albert Nobbs” (2011)
Rodrigo García’s drama “Albert Nobbs” walks a fascinating line in exploring its eponymous character’s identity. In an Oscar-nominated performance, Glenn Close stars as Nobbs, a woman living as a man in order to find work in 19th-century Ireland. In her male guise, Albert works as a waiter at a hotel, saving all of her earnings to buy a tobacco shop of her own. But while our initial understanding of the character is that of a woman posing as a man, Albert exists in a more complex liminal space. When her backstory is finally revealed — she was abandoned by her parents and brutally gang raped — it becomes clear that Albert identifies exclusively with the male gender, and that her guise is more complex and hard to understand than simply as an act of “crossdressing.” Close achieves the inexplicable balance of revealing the humanness of her unique character, and she forces the audience not to judge her actions but to explore them and their relationship to trauma and strength.
Bernadette Bassinger, “The Adventures of Priscilla, Queen of the Desert” (1994)
In “The Adventures of Priscilla, Queen of the Desert,” two drag queens (played by Hugo Weaving and Guy Pearce) tour the Australian Outback along with Bernadette Bassinger (Terence Stamp), a recently bereaved transgender woman. For a 1994 film, Bernadette is a fairly radical figure: Not only is she center-stage as openly transgender, but her definition as a character extends far beyond her gender or sexuality. She contends with grief and forms surprising new friendships as Stamp plays her subtly and sensitively. The Australian film, though controversial and still divisive, is seen as groundbreaking for LGBT representation on film as it achieved international success and even spawned a Broadway musical.
Brandon Teena, “Boys Don’t Cry” (1999)
Based on a true story, Kimberly Peirce’s 1999 drama serves as a serious reflection on the atrocious hate crimes that transgender individuals have to endure in the name of ignorance. In her Oscar-winning role, Hilary Swank gives a quiet, unforgettable soul to Brandon Teena, a boy trapped inside the body of a girl who chooses to fully embrace her male identity when she moves to a new town in Nebraska. It doesn’t take long for Brandon to assimilate and fall in love with the hometown beauty, Lana (Chloe Sevigny.) The two of them quickly find passion and enter a relationship that transcends the boundaries of sexual identity. But when Brandon’s big secret gets out, the town turns against him in a storm of violence, pain and trauma. Despite the tragedy of this, however, the beauty of Brandon’s character is his ability to love in a way that is pure, universal and deeply resonant.
Hedwig, “Hedwig and the Angry Inch” (2001)
John Cameron Mitchell’s film adaptation of his own Off-Broadway hit explores the crux of the transgender struggle by highlighting the universality that exists in how we perceive our own sense of self. While the punk/cult vibe of the film may seem like a niche decision, it addresses very complex themes of gender duality, infatuation and love. Mitchell plays Hedwig, a gay East German singer who survives a botched vaginoplasty surgery that leaves her with one “angry inch.” With love as the driving force in her life and her infectious glam rock n’ roll music, she tours the worst bars in America with her band, spreading her ideology of acceptance and gender defiance while dealing with her own fractured individuality. As she sings in the magnificent ballad “Origin of Love,” everyone has a duality inside them whether they like it or not, and only when you embrace both parts of yourself can you love unconditionally.
Laure/Mikäel, “Tomboy” (2011)
An emotional tour-de-force, Céline Sciamma’s French drama meditates on complex themes of ambiguous gender identification. Zoé Héran stars as 10-year-old Laure, who seemingly identifies as male based on how she introduces herself to others as Mikäel and goes to certain lengths to conceal her female body parts. Much of the drama’s mastery is how Sciamma doesn’t assign her young protagonist a definitive gender — a lot of our first encounters with the character occur while we’re unsure of her assigned gender — instead opting to keep the ambiguity of her identity alive so that Héran’s performance can speak to universal truths of acceptance and interdependence without being tied down to male or female constraints. As Mikäel befriends a young neighbor, Lisa, and gains the support of her younger sister and her mother, the character becomes a beautiful metaphor for the way gender is used as both a gateway to others and a protective shield against them.
Ludovic ‘Ludo’ Fabre, “Ma vie en rose” (1997)
The quietly radical and impressively nuanced “Ma vie en rose” tackles the very notion of transgender identity. Set in Belgium, it tells the story of Ludovic, a child born male who communicates being a girl internally and externally. The film is meditative and reliant on interaction, exploring without overt dramatics the family’s struggle to understand the child’s gender expression. Along with “Tomboy,” “Ma vie en rose” confronts the relatively untouched topic of being transgender as a child, making the case by smartly telling its story from Ludovic’s innocent point-of-view. For this reason, Ludo is a character you can’t help but empathize with — she isn’t making a choice or merely “dressing up,” she’s realizing from a young age just exactly who she is.
Marieta, “20 Centimetros” (2005)
Director Ramón Salazar’s evocative “20 Centimetros” tells the story of Marieta (Mónica Cervera), a narcoleptic transgender woman whose ultimate goal is to have gender reassignment surgery and become the glamorous woman she dreams of. The influence of Pedro Almodovar looms heavily here, as Salazar intoxicatingly mixes stylistic flamboyance with profound empathy to provide an effective albeit unusual character study. There’s an undying spirit to Marieta that never ceases. Through the majority of the film, she dreams up elaborate musical numbers in which she’s the star; in these moments, her beauty, and the tragedy of how she can only be her real self in her imagination, simply radiates.
Parinya Charoenphol, “Beautiful Boxer” (2004)
“Beautiful Boxer” definitively recounts the extraordinary life of Parinya Charoenphol, a Thai boxing champion who spent her victory earnings on gender reassignment surgery. Referred to as a “kathoey” in her home country, Parinya stunned the world as a teenager: Whilst donning makeup and being referred to as a “ladyboy,” she handily defeated (and kissed) her muscular male opponent. As directed by Ekachai Uekrongtham and brought to life by actor Asanee Suwan, “Beautiful Boxer” cathartically pays homage to her story, honoring her transition and praising her strength while also telling an enthralling tale of triumph in the process. The New York Times’ Dana Stevens may have put it best in her review by calling it “a rare hybrid: an underdog sports picture that’s also a transgender fairy tale.”
Rayon, “Dallas Buyers Club” (2013)
Jared Leto proved himself an actor worth lauding in his Oscar-winning turn as Rayon, an AIDS-stricken trans woman who cautiously begins a working relationship with a dying heterosexual who has much contempt for the LGBTQ community. Leto plays the role with a gentleness that really situates the audience and Rayon in the reality of the AIDS epidemic. As death gets closer everyday and she begins losing a dramatic amount of weight, Rayon preserves her grace, firm sense of self and humble sass, which makes her a lynchpin of her employer’s movement to prolong the lives of as many sick men and women as possible. Ultimately, Rayon becomes the vital life support through which her homophobic boss learns to truly, daringly live.
Rusty, “Flawless” (1999)
Counterculture and cops converge in “Flawless” through two powerhouse actors: Robert De Niro and the late Philip Seymour Hoffman. DeNiro plays Walt, a crowned NYPD hero who begrudgingly lives in a building with drag queens. When Walt gets caught up in a shooting in his apartment, he finds himself paralyzed with a speech impediment. As a form of speech therapy, he reaches out to Rusty (Philip Seymour Hoffman,) a musically talented transsexual in desperate need of money for her sex change. Though the movie received mixed reviews, Hoffman plays his character with an undeniable spirit, providing a biting, playful chemistry with De Niro that he powerfully contrast with a more reflective quietness in his solo moments. In Hoffman’s hands, Rusty gives flamboyancy a delicate, nuanced spin.
Sabrina “Bree” Osbourne, “Transamerica” (2005)
In the middle of her tenure on “Desperate Housewives,” Felicity Huffman earned a Best Actress Oscar nomination for her startling portrayal of Sabrina “Bree” Osbourne, a transexual woman who finds out she has a long lost son and travels cross country with him while pretending to be a Christian missionary. While the plot takes a rather predictable path, it’s Bree’s maternal awakening that makes the drama such a sensitive experience. Bree’s mission begins out of selfishness — her therapist won’t sign off on her vaginoplasty surgery unless she meets her son — but as she learns more about her offspring and reconnects with him, her priorities and own self-image begin to change. Beautifully tracked by Huffman, Bree’s arc speaks more to the bonds of family than it does to the confines of gender, for it’s her son and her acceptance of motherhood, and not just her surgery, that ultimately puts her at peace with herself.
Sin-Dee and Alexandra, “Tangerine” (2015)
Writer-director Sean Baker’s “Tangerine” is a shrewd character study involving two transgender prostitutes. The film follows the duo as they wander Los Angeles in search of a pimp boyfriend who may be unfaithful. Set over the course of a single day and shot entirely using an iPhone, the vibrant movie gets an extra pulse from its leading ladies, who are as wild, messy, abrasive and complicated as any character from the Harmony Korine universe. Transgender actors Kitana Kiki Rodriguez and May Taylor turn the movie into a highly unique buddy comedy as their characters, Sin-Dee and Alexandra, undergo a series of misadventures. In their unpredictable hands, their characters’ journey becomes a mad screwball comedy, which goes a long way in making their tale a universally relatable and charming story of friendship.
Stéphanie, “Wild Side” (2004)
Sébastien Lifshitz’s “Wild Side” tests the limits of love and friendship as it chronicles the relationship between Stéphanie, a pre-operative transsexual prostitute, and her two flatmates, an Algerian hustler and a runaway Russian soldier. When Stéphanie’s unaccepting mother falls ill, she travels back home to take care of her, only for her flatmates to follow along and fall in love with her. Surprisingly, she opts to love both in an open relationship, and Lifshitz visualizes their odd love triangle with an art house lyricism that is both intoxicating and hard to penetrate. You only get a hint of why Stéphanie acts the way she does, but it’s in this ambiguity where character gains its power. The way in which her unusual position liberates her from the sadness and uncertainty of her mother’s sickness cements the power of love to heal wounds we so desperately want to reject. It’s here where Stéphanie becomes vulnerably humane despite an open relationship many may find themselves stigmatizing.
Veronica, “En Soap” (2006)
Darkly funny yet deeply tragic, Pernille Fischer Christensen’s relationship melodrama “En Soap” is a stinging account of gender and love. The film tracks the budding romance between discontented domestic Charlotte (Trine Dyrholm) and Veronica (David Dencik), a transgender woman anxiously awaiting approval of the Danish government for gender reassignment surgery. Startlingly naturalistic, “En Soap” heavily relies on its characters to push the conceit that love can render sexuality malleable. But even if the film doesn’t quite live up to its intellectual potential, David Dencik rises to the occasion as Veronica, internalizing her loneliness and crisis of identity with dramatic depth and unexpected comedic bite.