Culture Slut: The Era of Escola
The name on the theatre world’s lips at the moment is the newest recipient of the Tony award for Best Actor in a Play, the enigmatic, the talented, the hilarious Cole Escola. But who exactly are they? I feel as if Cole’s rise to fame has been highly documented in America, with their appearances on talk shows and bit parts on shows like Big Mouth and Ziwe, but after this giant year, their presence is being noted by the rest of the world too.
Cole’s original off-broadway play Oh Mary! (both written by and starring Escola) transferred to Broadway where it became the toast of New York, garnering nominations left, right and centre, including two Tony nods and a runner up position for the Pulitzer Prize for Drama. They made a fabulous appearance at the Met Gala back in May, managing to score sartorial points at the the best dressed party of the year, and then made waves again turning up to the Tonys in a beautiful recreation of Bernadette Peters’ acceptance look from the same ceremony in 1999, becoming the first non-binary actor in history to win the in the Best Actor category.
I first became aware of Cole Escola thanks to a strange little film called Please Baby Please, a queer musical drama directed by Amanda Kramer, released in 2022. I wouldn’t necessarily say it was a great film, but it’s utterly fascinating. Angela Riseborough plays a bored wife struggling with her own gender restrictions, expressing her desires to lead a more masculine life, and ultimately know the feeling of being punched in the face. Harry Melling plays her husband, who has his own repressed sexuality journey to explore. Melling, a veteran of the cursed Harry Potter movies has followed in Daniel Radcliffe’s footsteps, in that he has since chosen interesting and bizarre films to pursue (his latest role being as a submissive in the gay leather film Pillion starring Alexander Skarsgard).
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Please Baby Please also saw the return of Demi Moore, fresh off her fashionable face lift reveal, looking exceptionally glamorous and playing a mysterious neighbour, who, of course, went on to have the biggest year of her career with The Substance and her own Oscar nomination (a loss that still pains me to think about). But the standout performer here is definitely Cole Escola, who plays a terrible drag queen who sings a sad song in a phone booth. Draped in flowers and sparkles, they were completely mesmerising.
“The film has its flaws, but Escola’s performance was an absolute highlight, a perfect balance of pathos, comedy, absurdism and genuine emotion.”
These same qualities can be found in their seminal work Oh Mary! Set in the days preceding US President Abraham Lincoln’s assassination in a theatre, the play focuses on the neglected figure of Mary Todd Lincoln, a woman with hopes and dreams that far outstrip her husband’s political machinations. Described as a perfect mix of camp and discipline that keeps a real emotional depth beneath its absurdity, Mary speaks to the audience about her desire to get away from the American Civil War and her husband’s latent homosexuality to become a cabaret singer the likes of which the world has never seen. Critics praised Escola’s writing and performance, emphasising their success in creating a queer-infused, raucous, campy, silly, nasty, good theatre. What Escola personally describes as “the stupidest play,” the New York Times deemed it to be a perfect balance of chaotic comedy and choreographed precision, calling it, in fact, “one of the best crafted and most exactingly directed Broadway comedies in years.” High praise indeed.
Who was Escola before this monumental success though? Coming from small town Oregon, they moved to New York to study in Manhattan but quickly had to drop out after not being able to afford the tuition. “They wouldn’t let me take out anymore loans, which looking back is a godsend because now I don’t have any debt!” Escola quickly took any kind of performance role they could get their hands on, from Clifford the Big Red Dog at the Scholastic book fair to entertaining at children’s birthday parties, they did it all. They also spent time as the self-confessed “laziest prostitute” on Craigslist, complete with an extensive list of acts they refused to perform, which inevitably had to be combined with working at a vegan bakery just to make that elusive New York rent.
Escola’s flexible working hours worked for our benefit in the end, because it allowed them to explore their increasingly absurdist comedy stylings alongside queer comedian Jeffrey Self. The duo made YouTube videos together under the name Very Good Looking (VGL) Gay Boys, which quickly got them the attention of Logo TV, the network behind the initial seasons of cultural juggernaut RuPaul’s Drag Race (tangent: why hasn’t Cole been a guest judge on Drag Race yet? As of time of writing they are slated to be on the new drag show King of Drag as a judge, but still no Drag Race recognition).
Escola and Self’s early videos are still available on YouTube, and I highly recommend tracking them down. Self takes on the role of the comedic straight man, letting Escola float off on tangents and into the realms of surrealist nonsense, whether that’s enacting a whole cinematic breakdown of a relationship in their video about the legalisation of gay marriage, or the lengths they find themselves prepared to go to trying to get tickets to the midnight screening of the Sex and the City film.
Jeffrey & Cole Casserole ran on Logo for two seasons and became a certified cult classic. It also opened doors for Escola to take on other TV projects in the years to follow, playing a role written for them specifically in the Hulu series Difficult People alongside stars like Billy Eichner and Julie Klausner. Soon, Escola was everywhere, working with the legendary Amy Sedaris, showing up in the popular series Search Party, voice acting on the Cartoon Network show Criag of the Creek, for puberty-based comedy Big Mouth, and vampire mockumentary What We Do In The Shadows. The 2020s has truly become the Era of Escola.
With so many glittering achievements and appearances, from their outrageous fashion moments on the red carpets to the celebrity photos in the dressing room after Oh Mary! (Kylie and Timothee, Robert Downey Jr., King Princess, MERYL STREEP), it can be hard to remember Cole’s tentative beginnings.
One thing that can truly highlight this growth, and provide a full circle moment, is buried deep in the VGL Gay Boys archive. Escola, in a fried, curly wig enters the video claiming to be Bernadette Peters, disrupting Self’s plans and being charmingly bizarre. The year is 2008. Last month, in 2025, Escola accepted their own Tony Award dressed in a beautiful blue gown and a much more expensive wig, emulating Bernadette Peters’ legendary 1999 win. She’s still here. She’s made it. The world’s laziest prostitute takes their place amongst some of the most admired comedic Broadway actors of this century, and New York shines all the brighter for it.
