In this edition of our Trailblazer series, we’re putting the spotlight on someone who doesn’t just break the mold; they melt it down and turn it into something absolutely unhinged and utterly brilliant. Meet Cole Escola: writer, actor, comedian, and newly minted Tony winner. Whether playing Mary Todd Lincoln in a whiskey-fueled spiral or voicing an animated misfit, Escola brings a bold sense of humor and heart to everything they touch. From small-town Oregon to Broadway’s biggest night, they’re redefining what a theatre star can look like — and having a blast doing it.
Born and raised in the small town of Clatskanie, Oregon, Escola’s path to the stage was anything but ordinary. After surviving a traumatic childhood, they found solace and expression in community theatre, lighting up high school productions of Les Misérables, Fiddler on the Roof, and Little Shop of Horrors. After a brief stint at Marymount Manhattan College, Escola dove headfirst into New York’s performance scene. Their comedic timing, absurdist sensibility, and love of character work quickly found a home in the downtown cabaret circuit.
Their early YouTube collaborations with Jeffery Self, known as the “Very Good Looking (VGL) Gay Boys,” evolved into the cult hit Jeffery & Cole Casserole on Logo TV in 2009. What began as DIY sketch comedy blossomed into a multifaceted screen career, marked by memorable roles in Difficult People, Search Party, At Home with Amy Sedaris, and Big Mouth. Whether voicing animated misfits or portraying live-action eccentrics, Escola has always embraced the weird, the wonderful, and the wholly original. Wherever there was a misfit, Escola made them magic.
After years of selling out cabaret shows and delivering scene-stealing performances on screen, Escola made their Broadway debut with Oh, Mary!, a production they wrote, starred in, and developed alongside director Sam Pinkleton. The show first ran off-Broadway at the Lucille Lortel Theatre to critical acclaim. Its subsequent Broadway transfer brought a surge of energy to the 2024–2025 season. Critics hailed the play as “wickedly funny” and “unlike anything else on Broadway,” while audiences embraced Escola’s bold vision and layered performance.
Accolades quickly followed. Escola’s work on Oh, Mary! earned them a Tony Award, a Drama Desk Award, a Theatre World Award, and an Outer Critics Circle Award. The play was even named a finalist for the Pulitzer Prize for Drama — a rare feat for a debut Broadway playwright.
Last Sunday, Cole Escola made history at the 2025 Tony Awards with a win that was as emotional as it was electric. Taking home the award for Best Performance by a Leading Actor in a Play, Escola was honored for their unforgettable portrayal of Mary Todd Lincoln in Oh, Mary!. This moment was a landmark — not only for Escola’s career but for Broadway itself. It marked the first time a non-binary performer had ever received this award, signaling a long-overdue shift toward broader representation in the industry.
Draped in a vintage gown and exuding the off-kilter charisma fans adore, Escola delivered a speech that was both heartfelt and hilariously surreal. They thanked their collaborators, their younger self, and “every weird theatre kid who’s ever been told they were too much.” The standing ovation that followed felt like a collective exhale — a moment of recognition not just for talent, but for authenticity.
In an interview with Entertainment Tonight, Cole shared, “I can’t decide what it means for other people. I’m only me, so I can only see things through my own eyes.”
With that win, Escola didn’t just take the stage; they took their place in theatre history. And somehow, we get the feeling this is only the beginning.
What makes Escola a true trailblazer isn’t just their fearlessness on stage; it’s their insistence that theatre can be a space for weirdos, outcasts, and anyone who’s ever felt like they didn’t belong. They write characters who live at the margins and then put them center stage, with nuance, absurdity, and deep emotional truth.
They’ve proven that camp can coexist with craft, that comedy can be smart and subversive, and that representation goes beyond casting — it’s also about who gets to tell the stories. Escola’s work doesn’t just push boundaries; it reimagines the entire stage.
And while Oh, Mary! may have introduced them to Broadway’s biggest audiences, longtime fans know this is only the beginning of a much bigger, stranger, and more fabulous era in theatre, with Cole Escola leading the charge.
Cole Escola’s rise isn’t just a personal triumph — it’s a reflection of what’s possible when artists are empowered to bring their full selves to the stage. Behind every trailblazer is a community, and countless organizations have been working to amplify their stories and creators long before Broadway caught up. If Escola’s story moved you, consider supporting one of the following groups that are helping build a more inclusive, vibrant future for the theatre world:
Cole Escola’s journey reminds us that theatre thrives when it embraces boldness, authenticity, and the voices of those who dare to be different.