Boy Meets Girl (2014)
Rotten Tomatoes score: 86%
In the fresh and modern Boy Meets Girl, the character in question’s trans identity feels almost incidental. This, despite it having the world’s most crushingly boring and predictable title – but don’t be fooled: it’s not your average, cliche-ridden romcom.
It stars trans actress Michelle Hendley as trans 21-year-old Ricky. Passing time in her dull Kentucky hometown, Ricky is dreaming of bigger and better things. Life suddenly gets interesting – and considerably more complicated – when she attracts the affection of Francesca, who has a boyfriend…
Rotten Tomatoes score: 77%
Desperate Housewives star Felicity Huffman was Oscar-nominated for her work in this naturalistic drama about a trans woman who finds out, post-transition, that she parented a son many years before.
Huffman creates a personality for Bree that is nothing like her own: a coy and meek woman, simply getting on with life. A shrinking violet compared to the ball of aggressive energy that is her newfound son. She’s reluctant to invite drama into her life; wants to cut ties with her past. But an instinctive pull of love draws her in. This allows for an unpredictable situation to be explored delicately. In other hands, it would no doubt have been sensationalized.
Rotten Tomatoes score: 97%
It’s of course the legendary ‘iPhone movie’ filmed entirely on a cellphone – but in reality, Tangerine is much more than that. It features not one, but two powerful, compelling trans characters, played by powerful, compelling trans actresses: Sin-Dee Rella and Alexandra, played by Kitana Kiki Rodriguez and Mya Taylor.
It’s also up there with the best friendship films of all time (move over Thelma and Louise). In it, two sex workers trawl the streets of Hollywood looking for Sin-Dee’s cheating pimp lover, to teach him a lesson he’ll never forget. There’s riotous, cartoonish violence aplenty, but also a throbbing emotional heart that you don’t immediately notice.
The Danish Girl (2015)
Rotten Tomatoes score: 68%
While Tangerine and its stars were criminally overlooked at the Oscars, The Danish Girl received four nominations, including one for Best Actor for Eddie Redmayne. His costar Alicia Vikander won Best Supporting Actress.
Redmayne plays artist Lili Elbe, one of the first people in the world to undergo gender reassignment surgery. Sadly, she died in 1931 due to an infection arising from the surgery. Thankfully, this graceful, gentle movie doesn’t linger on the tragedy, but rather focuses on the beautiful story of Lili and her partner Gerda (Vikander), whose relationship evolves as Lili explores her gender identity.
Dallas Buyers Club (2014)
Rotten Tomatoes score: 93%
Meanwhile, Jared Leto won the Best Supporting Actor Oscar for his portrayal of Rayon, a drug addicted trans woman with HIV in the 1980s. With her delicate beauty and easy charm, she challenges the prejudices and toxic masculinity of Matthew McConaughey’s Ron, a drug smuggler and fellow HIV sufferer, whose path crosses with Rayon’s.
Criticism for Leto’s Oscar was fierce in some corners of the trans community, who believed the role should have gone to a trans woman. Indeed, such observations have been made about many of the actors and actresses in this list, as excellent as their performances may be.
Boys Don’t Cry (1999)
Rotten Tomatoes score: 88%
Like Hilary Swank in Boys Don’t Cry, for example. The real-life-and-death story of Brandon Teena at the hands of Nebraska transphobes is truly heartbreaking, and this profoundly affecting movie about his life is, understandably, an emotional juggernaut to watch. But it’s fantastic that Brandon’s story was brought to global attention.
Hilary, who plays Brandon flawlessly, won the first of her two Best Actress Oscars for the role. She would later win her second in 2004 for Million Dollar Baby. The film also provided Chloe Sevigny with her Oscar-nominated breakthrough role; she plays Brandon’s love interest, Lana.
Desperate Living (1977)
Rotten Tomatoes score: 70%
’It’s contagious, it’s outrageous, it’s John Waters Desperate Living’ – so says the tagline of Waters’ ninth feature film. (True, it could be used to describe any of them!). This is a hidden gem of Waters’ filmography, often obscured by the more beloved Pink Flamingos and commercially-successful Hairspray.
The typically surreal plot focuses on a neurotic housewife and her housemaid, exiled to a shantytown when the latter murders the former’s husband. There they meet Mole – who early on declares ‘I’m a man trapped in a woman’s body’ – and Mole’s lover, Muffy. Gender identity is explored throughout the film in a brash, direct and humorous way, but it’s arguably never exploitative: a wonder for a film of its era.
52 Tuesdays (2015)
Rotten Tomatoes score: 88%
52 Tuesdays was filmed over the course of a year, every Tuesday, to give an authentic insight into the rocky but inspiring journey of James’ transition. Played with tenderness and nuance by gender non-comforming actor Del Herbert-Jane, his story is mainly told through the eyes of his daughter, Billie, whom he has dinner with once a week for a year, as he settles into his new life.
Although Billie, played with dynamism by fellow Australian Tilda Cobham-Hervey, struggles to support her parent’s voyage initially, love wins the day in this uplifting drama. The second best film in this feature.
Laurence Anyways (2012)
Rotten Tomatoes score: 83%
Finally, for this writer’s money, the best film on this list! Directing prodigy Xavier Dolan has extensively explored LGBTI lives in his fantastic oeuvre. In one of his most critically-acclaimed movies, Laurence Anyways, he delves into the intense, shifting connection of two lovers across a 10-year period, during which one of them transitions gender. It’s an emotional epic.
In this adorable interview, Xavier explains that the story was inspired by a real life couple. As such the trans character, Laurence, feels remarkably true-to-life, furthermore heightened by the film’s intimate, documentary-like tone. Laurence is played exquisitely by Melvil Poupaud, and Laurence’s partner Fred, played by Suzanne Clément, is similarly irresistible. Of course, they’re the kind of couple we all wish we knew. Simply wonderful.