In 1999, the relatively unknown Hilary Swank won the Best Actress Academy Award for Boys Don't Cry. Swank plays Brandon, a transgender boy who was born a girl, who starts a new life in Nebraska. But his new life as "one of the lads" is torn apart when his secret is outed in the community. In this tender and balanced portrayal of transgenderism, Swank brought a beautifully subtle character to life that had rarely been seen on the big screen before. Though the story is bleak and the circumstances extraordinary, it is the ordinariness of Swank's character that made her so compelling. And the story is a heartbreaking tale.
9. TRICK (1999)
A young inexperienced gay musicals director meets a go-go dancer on a night out and thinks he hasn’t got a chance with the muscle-bound Adonis. When the dancer actually shows an interest in him, the pair come up against scores of obstacles that prevent them from having sex over the course of the night, including the meddling of his super-camp best friend Tori Spelling and a vengeful drag queen, Coco Peru. A delightfully twee but fun rom-com, this is 90s indie cinema at its best.
8. BUT I'M A CHEERLEADER (1999)
In this camp but heartfelt comedy, a teenage girl is sent to Gay Camp when her parents suspect she might be a lesbian. Though the trip is meant to "cure" her of any burgeoning homosexual feelings, her experiences with her fellow homosexuals leads to a solidarity intent on defying the system, rather than conforming. A pacy, funny and daft romp, But I'm A Cheerleader is a hilariously irreverent take on a serious problem in America, but the result is incredibly entertaining. And Lyonne and DuVall were born to play these roles.
7. THE BIRDCAGE (1996)
The Hollywood remake of the aforementioned La Cage Au Folles, The Birdcage is a camp and catty battle of wits between drama queens, bitches and bigots, cannon-balling through witty dialogue and larger-than-life explosive scenes. With Williams at the height of his fame, this madcap comedy is a hilarious and riotous comedy that accepts Gay Culture at its most exaggerated, with its campery played for laughs, but not the butt of its jokes. And Nathan Lane is absolutely divine here.
6. ALL ABOUT MY MOTHER (1999)
All About My Mother is a fabulous film. A young man wants to uncover the identity of his father, but his mother is intent on keeping this secret. With Spain portrayed in colourful vibrancy, the film explores the relationship between a mother and son, with inter-textual references to every film about strong women you can think of and Roth is resplendent in the central role. Add to that a fabulous transsexual and a truly endearing nun with HIV, played by Penelope Cruz, and this is a film that will take you on a rollercoaster of emotions. Just like any Almodovar film, this is a celebration of how colourful life can be, but this is his very best film of all.
5. MY OWN PRIVATE IDAHO (1991)
Van Sant makes two types of films; the accessible and the arty. My Own Private Idaho is definitely the latter, but this juxtaposition of Shakespearean themes, plot and dialogue (lifted unpretentiously from Henry IV Part I, Part 2 and Henry V) and the gay hustling scene of the early 90s somehow just works. This dreamlike and sad tale of two boys hunting for somewhere they can call their home is a tragic and haunting indie with pretentions of epic grandeur. Though not easily accessible, its concept is so high that its poetic ramblings are soothing and shocking in equal part. And moments of brilliance flash from Phoenix, showing the actor that maybe he could have become.
4. PARIS IS BURNING (1990)
The impact this remarkable documentary has made cannot be understated. Charting New York's drag scene in the 1980s, the film focuses on the malleability of Queer Culture, where everyone expresses who they want to be, but obviously being fierce at the same time. Observing the balls, chronicling the voguing and meeting with people from the city's leading drag families, it peels back the layers of these warm but damaged people, who have created the world where they can feel accepted. A funny film, laden with sass, Paris Is Burning spread the New York drag model around the world and shaped a whole generation of queens. And now it lives as a remarkable document of a bygone age.
3. ORLANDO (1992)
A gender-bending time travelling disbelief-suspended masterpiece, stars Swinton as the young nobleman Orlando. Commanded by Queen Elizabeth I (played with glorious campery by Quentin Crisp) to stay forever young, he does exactly that. Over the resulting centuries, he experiences British history from multiple angles, lives, relationships, even changing gender midway through. Running right until the 1990s, the character grows wiser but never loses the wide-eyed fervour of the young bewitched man. Swinton is resplendent in this Queer punk film that defies societal conventions and tips its hat to Derek Jarman at every opportunity.
2. THE ADVENTURES OF PRISCILLA, QUEEN OF THE DESERT (1994)
Despite its appallingly tacky incarnation on the stage, this bitchy and fabulous road movie remains one of the finest (and most original) of its genre. Travelling across the Australian outback to perform cabaret at Alice Springs, two drag queens and a transsexual inhabit a pink second-hand bus that takes them across the literal wilderness, as well as taking them on a journey through the wildernesses of their own lives. Despite their brazen flamboyance, none of them have come to terms with who they really are and while tempers, egos and wigs fray, so each one comes closer to discovering their true selves. This is a story about everyone's self-acceptance, but it's dragged up in heels and corsets and some of the boldest drag you will ever see on film. Stamp is the stand-out, but they are all on point. Particularly their lip-syncs to an amazing soundtrack.
1. BEAUTIFUL THING (1996)
Two teenage neighbours find themselves sharing a bed one night, only to discover new feelings that they don't understand. Coming to understand their sexuality and their feelings for each other, this compelling story of sexual awakening is a life affirming ode to teenage love and a mirror held up to society's inherent homophobia in equal measure. Based on the play by Jonathan Harvey, this landmark film showed the innocence of same-sex love without any associated adult corruption that many still believe comes with homosexuality. Beautiful Thing shows that all love really is a beautiful thing and set against the soaring soundtrack of Mama Cass, the film is a beautiful thing in itself.