Hollywood has come a long way in its depiction of queer characters, and modern classics like Portrait of a Lady on Fire and Moonlight prove that. But not every queer story has to be so deadly serious. This list of Pride-friendly comedies is a joy to watch. Some of them hold up better in the present day than others, even if all are coming from the right place. Some are groundbreaking for their era, some subvert our perception of previous eras, and some are a product of the (maybe) more tolerant world we live in today. But most importantly, all depict three-dimensional queer characters, complete with unique traits, weaknesses, and eccentricities.
Fire Island (2022)
Just in time for the summer comes this queer-ified retelling of Jane Austen’s Pride and Prejudice, written by and starring Joel Kim Booster. For one week out of the year, serial flirt Noah (Booster), his introverted best friend Howie (Bowen Yang) and their tight-knit friend group get to exist in a space absence of all straightness: Fire Island. But their troubles are far from over; amidst all the drugs and hookups, the friends have to navigate the racial and economic divides that rule the island. Like Elizabeth Bennett before him, Noah begins to have his preconceived notions of who he is and what he wants shattered. The story beats are familiar, and they are designed that way. But it’s the richness and details of the world that stand out, the little moments of relatable embarrassment, that linger after the credits roll. And it might make you want to have a good time.
But I’m a Cheerleader (1999)
Director Jamie Babbitt describes her first feature film as “Barbie Dream House meets Edward Scissorhands,” and there’s no better way to explain its zany tone. The story of Megan Bloomfield (Natasha Lyonne) and the friends and lovers she meets at a gay conversion camp pokes fun at everything and everyone. Blisteringly dark humor lurks beneath the eye-popping set design, mimicking the sadistic underbelly of a cheery brainwashing operation. Critics and audiences didn’t know how to react to this subversive, campy flick when it came out, but its cult status proves how ahead of its time it was. It doesn’t hurt that it features queer icons such as Lyonne, Clea DuVall, and the one and only Rupaul.
The Birdcage (1996)
Like Cheerleader, this offering from the legendary duo of Elaine May and Mike Nichols (and Emmanuel Lubezki manning the camera) is a colorful joy to look at. In a very gay South Beach, drag club owners Armand and Albert Goldman (Robin Williams and Nathan Lane) are coaxed by their son into appearing straight to appease his soon-to-be father-in-law, Republican senator Kevin Keeley (Gene Hackman). A joyful skewering of conservative values ensues, and the ending set piece where the Goldmans pretend to be a “conventional” family is a masterclass in comedy direction. Maybe the most endearing aspect of this film is the depth and nuance of Williams’ performance, operating in more restrained territory than usual. He is flamboyant but charming, serious, and ultimately unafraid to be his true self.
Tangerine (2015)
There, unfortunately, aren’t many comedies about transgender people or sex workers, but Sean Baker’s breakthrough hits both bases. Touted for its innovative use of iPhone cinematography, Tangerine deserves just as much credit for depicting a subculture rarely shown in Hollywood, while fully humanizing everybody involved. Fresh out of jail, Sin-Dee (Kitana Rodriguez) tracks down her cheating pimp boyfriend (James Ransome) with the help of her friend Alexandra (Mya Taylor). Chaos and hilarity ensue. But even as we laugh at the absurd situations most of us will never encounter, it is never at the expense of the richly realized characters. This rollercoaster fluctuates between comic and tragic, but always feels real.
The Favourite (2018)
If Portrait of a Lady on Fire is a queer subversion of 18th-century aristocracy, then The Favourite is its mischievous little sister. Surprisingly, this is the one based on a true story: a love triangle between Queen Anne (Olivia Coleman), Sarah Churchill (Rachel Weisz), and her cousin, Abigail Masham (Emma Stone). A typically raunchy venture from Yorgos Lanthimos, much of the delight comes from the contrast between the stuffy royal outfits and inventively vulgar dialogue, the hilarious rivalry between Sarah and Abigail, and the romantic intrigue. But Coleman’s Oscar-winning star turn steals the show, painting a sad portrait of the lonely, childish queen, unsure of what to do with all the attention lavished on her.
I Love You, Phillip Morris (2009)
This underrated rom-com did not make much of a buzz upon release, but it features arguably the purest romance on this list, based on a firecracker of a true story. Con man Steven Jay Russell (Jim Carrey) falls in love with Phillip Morris (Ewan McGregor) while in prison. When Phillip’s sentence is up, Steven breaks out of jail to be with him, which he will do four different times. Carrey is in vintage form as a totally off-the-rails con-man, and he is a perfect match for McGregor’s soft-spoken support system. The epic obstacles standing in the way of their romance make this an interesting hybrid of thriller, romance, and comedy. The daring balance pays off well, resulting in a thrilling, funny, and heartwarming film experience.
Kissing Jessica Stein (2001)
This film should be placed in a time capsule. Written by the two stars, Jennifer Westfeldt and Heather Jurgensen, the story is pretty mundane by contemporary standards. Jessica Stein (Westfeldt) is a neurotic New York copy editor who just needs to loosen up. She ends up stumbling into a romance with the more adventurous art gallery attendant Helen Cooper (Jurgensen). While opening her mind, the relationship also leads to a bit of an identity crisis. A liberal New Yorker exploring her sexuality sounds like an incomplete thought today, not a full-length feature film. It even ends up indicating that all of this playing around just helped her discover what she really needed: a decent man! But it features astute observations about romance and sexuality, and should be especially commended for its willingness to have these frank discussions in an era where this was new ground for the mainstream.
Shiva Baby (2020)
Some might venture to call it the queer Uncut Gems, with Jewish signifiers and neuroticism so baked into its ethos. Rachel Sennott stars as Danielle, a young woman stuck in a Shiva from hell that would make Howie Ratner blush. It’s bad enough when your sugar daddy shows up at a family Shiva with his wife; make it double when random relatives pepper you with questions about your career plans. God forbid your ex-girlfriend shows up. A 77-minute pressure cooker of a chamber piece, Shiva Baby is refreshingly contemporary look at the stresses of young adulthood, and in contrast to Kissing Jessica Stein, its nonchalant treatment of Danielle’s bisexuality shows how far the film industry has come in depicting queer relationships.