Silver Anniversary Celluloid
The film industry cranked out so many amazing films a quarter-century ago that many film scholars would like to challenge the notion that 1939 (Gone with the Wind, The Wizard of Oz, Love Affair, Frankenstein, Mr. Smith Goes to Washington, The Women, Ninotchka, and more) was the best year in American film history. Instead, they say, the honor should go to 1999. With films as diverse and superb as Fight Club, The Matrix, Office Space, Election, The Blair Witch Project, The Sixth Sense, Being John Malkovich, and The Virgin Suicides (and more!), the idea certainly has legs.
For queer movie buffs, looking back on these silver anniversary films can be enlightening, instructive, and perhaps a little enraging to see how we were seen and talked about in the waning days of the 20th century. Filmed entertainment, like no other art form, offers a visceral experience of history, as it allows us to see and hear stories from the past, exactly as they were seen and heard before.
Flawless was a “crime comedy-drama” released in 1999. And if that sounds like a lot, you’re not far off. Robert de Niro played Walt, a security guard recovering from a stroke, opposite Philip Seymour Hoffman as Rusty, a pre-operative trans woman who gives Walt singing lessons to help him regain his speech. There could have been some lovely commentary there about finding one’s authentic voice and how music, so evocative of feeling, is often a better conduit than the more logical and unadorned spoken word.
But sadly, that level of nuance can’t exist alongside a wild storyline about a mob boss that Rusty had stolen from to pay for her gender transition, and the whole thing is a bit of a mess. I feel fairly confident that Flawless is not one of the films that scholars are using to argue the case for 1999 as the best year in film. But while the movie hasn’t aged all that well, Hoffman’s performance (he, of course, would later win an Oscar for playing gay writer Truman Capote) is captivating. He chews the scenery while avoiding any offensive clichés. In a film that bears almost no resemblance to reality, he creates something real, and that’s pretty flawless.
Cruel Intentions was a teenage adaptation of Dangerous Liaisons (let that just sink in; take all the time you need) starring Sarah Michelle Gellar, Ryan Phillippe, and Reese Witherspoon. While most don’t think of it as a queer film, per se, its most iconic moment takes place when Kathryn (Gellar) takes time to teach Cecile (Selma Blair) how to kiss, with lots of tongue.
More important to the plot is another moment when closeted football player Greg (Eric Mabius) is blackmailed by Sebastian (Phillippe) with pictures of Greg in bed with another boy. So…girl-on-girl is hot, but only if neither of the girls are actually into other girls, while boy-on-boy is decidedly not. If you want a night of campy fun, this might fit the bill, but the 1988 grown-up adaptation is better in every way, and also less insulting.
The Talented Mr. Ripley is a much better film than these other two. It’s a prestige drama featuring lush Italian landscapes, an Oscar-nominated performance by Jude Law, and a gay protagonist who just happens to be a serial killer and pathological liar. And yet…it’s absolutely worth revisiting, honest. While the main character does many awful things, the film wants you to like him, and even root for him. Even as you watch him seethe with jealousy, deceive his so-called friends, and kill the ones he loves, you might not condone his terrible choices, but you understand why he’s doing what he’s doing, and you empathize with him.
Twenty-five years later, I’m still not sure how this movie pulls this off and given more recent productions like Saltburn (with an eerily similar plot) and Netflix’s Ripley (based on the same characters, created by lesbian author Patricia Highsmith), it’s a trick that still works.
The Best Actress winner of the maybe-best-year-ever-in-movies was an unknown before she made her film debut, playing a trans man in 1999’s Boys Don’t Cry. I recently learned that out director Kimberly Peirce wanted to cast a trans man as Brandon Teena, a real person who was raped and murdered in rural Nebraska in 1993, but after years of auditions, she opened the casting process to cisgender men and women.
It’s easy to see why she went with her eventual choice. As Brandon, Hilary Swank’s performance contains pathos, swagger, vulnerability, grit, and naïveté, often in the same scene. She earned every inch of that Oscar. And while the film is both literally and emotionally dark, Brandon lives on in the viewer’s memory as a puckish, optimistic Romeo.
These days, we’re happily more likely to see trans actors cast in trans roles, characterizations of gay people that are flawed and nuanced without entering serial killer territory, and queer love being celebrated rather than existing simply to titillate or scandalize. We’ve made a bit of progress, thankfully. Still, it’s fascinating to see just how much we were getting right a quarter-century ago. Pass the popcorn. ▼
Eric Peterson is Interim Managing Editor of Amble Press, a novelist (Loyalty, Love & Vermouth), and a diversity, equity, and inclusion practitioner. In his spare time, he hosts a podcast, The Rewind Project.