Before he made the decision to transition from female to male, Hennessy Winkler spent a long time thinking about what that would mean for his work as an actor. He had been successfully booking jobs. Was this the end of his career? Would the industry embrace his new identity? But his fears have been allayed; he is currently making his Broadway debut in Sweeney Todd, as one of the Main Stem’s first out trans male actors. “As soon as I started really coming into myself, being able to look in the mirror and recognize myself, people started wanting to work with me more,” he says.
There are very few out trans male actors on Broadway. In fact, the only other one Winkler is aware of is Jess Barbagallo, who was in the ensemble of Harry Potter and the Cursed Child. Originally from Hawaii, Winkler grew up in a religious household with a father who was a minister. He began performing as a child, and has graced regional stages and Off-Broadway’s La MaMa, Soho Playhouse, and New York Theatre Workshop. Then he landed a role he had dreamt of playing for a long time: Oklahoma!’s Will Parker, in the national tour of Daniel Fish’s take on the musical. Now, he’s made the jump to Broadway and is laying out his experiences, and their complexities, with a surprising level of vulnerability.
There’s no neat box to put Winkler’s story in. As someone whose performance career began in childhood and whose transition began much later, it’s been a long road. “For 10 years, I stayed without any sort of physical or social transition,” he says in a quiet, but self-assured voice. During that time, Winkler continued to present as female and try out for female roles. “One of the reasons I chose not to transition when I found the word transgender was because my audition book was all female songs. I had been attuned to female characters and shows, I was trained female as a dancer. And my voice was killer. I didn't want to give all that up, I didn't want to give all that training up and all that experience. And as an actress, I liked the product that I put out,” he shares candidly.
It’s a glimpse into the reality of what it means to transition as a performer and the repercussions it can have on your career. And it’s an experience Winkler has heard other trans singers and actors share: “That was a hard choice to be like, ‘OK, do I start all over when I worked so long and so hard to build this? Is anyone going to remember me?’”
The audition room is dreaded by all performers. But for Winkler, a new challenge arose for him after he began transitioning. “I've met casting directors who don't remember me, because I looked totally different. I did go through a transition period where I looked very nonbinary, I suppose. And that was hard for me too,” he admits.
At the time, casting directors were willing to see more trans actors. But it was clear to Winkler that they didn’t really know what they were looking for yet. Over the course of the pandemic, Winkler began to present more as himself. “By the time COVID was ending, the conversation was changing and people were being a little bit more thoughtful. I started getting cast in stuff the more I started looking like myself. It was me aligning with myself, I think, that started getting me more work,” he reflects.
Getting to that point has been difficult, he admits, “I was so scared before that maybe myself wasn't good enough.”
The pandemic was a turning point for him in the audition room. And after COVID, one of the first roles he got was Will Parker in the U.S. national tour of the Oklahoma! Broadway revival. “That was really affirming to me,” Winkler remarks. His experience in the national tour meant more to him than just finally getting to play a character that matched his identity. Being on stage in Oklahoma!, while out as a trans man, proved fulfilling as an advocate. “My favorite part was getting notes or being able to meet trans guys who were like, ‘I can't believe you're doing this, I didn't know that we could do this. Thanks for giving me hope,'” he recalls.
After that, with each audition, Winkler wondered whether he should disclose his trans male identity to casting directors. And it’s a dance that’s been changing as the theatre industry has faced more calls for diversity and inclusion in the past few years. “We're at a period of time right now when people are wanting to check some diversity boxes. There's a lot of game playing in this industry.” Winkler’s takeaway from that for other trans actors? “You’re allowed to play the game right back. If that makes you feel gross, fine. If it doesn't feel great, fine.” For himself, Winkler chooses to play. When he thinks disclosing his trans identity will help him land a role, he’ll happily check some “diversity boxes” for a production.
While he now auditions for male roles, Winkler admits he’s still adjusting. He struggles to connect completely with male roles, and all the societal stereotypes of male-ness that is placed on those characters. “I'm still in transition a little bit because I've been so coded to female roles and songs. I’m having a hard time with my book and finding songs for that,” he shares. “Vocally, I still do miss my singing voice and the things I could do with it. But, my voice now is my voice.”
It’s not hard to imagine, despite his bit of vocal dysphoria, why Winkler was cast in Sweeney Todd. There’s a clarity and strength to his voice that suits the demands of Sondheim’s music and lyrics. And it’s a testament to Winkler’s talents that he was cast as an ensemble member, as well as a swing for eight roles—it's a wide vocal demand, ranging from baritone to tenor notes.
With his experience and the success he’s had in recent years, Winkler has a lot of advice for trans actors going through their own journey while navigating industry setbacks. “There’s no wrong way to do this,” he advises. “You’re still a man or a woman, even if you don't look like one to the rest of the world. Transition doesn't make you anything. It's helped me be able to be seen as myself. And that was very good, but I really took my time with it. Go at your own pace."
He also recommends reaching out to other trans actors, not being scared to get off social media, and surrounding yourself with the people that see you. “And keep showing up,” Winkler says. “Keep going to auditions. Auditions suck for everyone. Sometimes, it's a numbers game, you know? And it's like that for everyone.”
In addition to his notes for trans actors, Winkler also has notes for the industry. His first? Trans men exist. “Trans male erasure is a real thing, especially in this industry,” he says. There’s a mix of disappointment and defiance underlying his tone. “Part of my advocacy is talking about my own experience, and letting people know that we're out here, as well. We just want to play the roles. We’re good. We show up. We have an extraordinary amount of training.”
Winkler hopes that the push towards inclusion includes more space for trans stories and trans characters, and importantly, to have trans actors playing such roles. At the same time, Winkler believes it’s also “really important” to have trans actors play cis roles. As he succinctly puts it: “We're storytellers first. We just happen to have this birthmark.”