Sex, drag and Whitney Houston: ‘Wake of a Dead Drag Queen’ returns with a flamboyant punch

In a second-floor rehearsal space in Ravenswood, actor Terry Guest straddles his scene partner. The two share a passionate kiss as the show’s intimacy director looks on, giving notes.

“After the kiss, can I run my hand up towards your booty?” that scene partner, co-star Paul Michael Thomson, asks during a scene break. Guest consents and the intimacy director, Victoria Nassif, notes the change.

“More booty should lead to more ticket sales,” jokes Guest.

He has a vested interest in such things, as the creator of "At the Wake of a Dead Drag Queen." The Story Theatre production, which begins previews April 26 at the Raven Theatre, is a tragic queer love story based on Guest’s uncle, a drag queen who died from complications of HIV.

Then an unknown playwright, Guest initially penned the script during President Donald Trump’s first term. After it debuted, the play — which Guest describes as a “sexy, hilarious, Southern Gothic epic” — went on to tour six cities.

“It makes me very proud of that kid for making it happen,” said Guest, thinking back to his younger self. He was 24 then and at a crossroads in his career. A leap of faith helped him pivot from acting to writing. “I decided to take a risk and try something that I was curious about but I’d never really done,” he said.

To Guest, who is a queer Black man, "At the Wake of a Dead Drag Queen" is personal, connecting him through the art form to his uncle and to Southern drag culture. This is the play that sparked his career, winning him awards and helping to pull himself out of despair when his acting career stalled.

But the play (which had its world premiere at Story Theatre in 2019), is also returning at a precipitous moment, as the federal government has cut funding for HIV research and prevention projects and as the National Endowment for the Arts has issued new guidelines saying it won’t fund arts groups that promote “diversity, equity and inclusion” or “gender ideology.”

The timing is not lost on its creator.

“It is a little disheartening, honestly, that the play is so relevant now,” said Guest.

A real-life character brought back from the dead

In "At the Wake of a Dead Drag Queen," the audience attends the funeral of a drag queen named Courtney Berringers. Before she’s laid to rest, Berringers leads the audience through her life, told through monologues and songs.

Guest plays Berringers, a character sprinkled with bits of his own experience. “The character really is an amalgamation of my uncle and of myself at 25, all blurred together,” he said.

Guest grew up in Georgia, where he started down his career path in a musical theater class while a freshman in high school.

“I didn’t really grow up around theater, so I didn’t know about this specific art form,” he said. “I just knew that I wanted to perform.”

Instantly, he was hooked: “I hadn't engaged with an art form at that point in my life that so many queer people were involved in. So, seeing and learning about all of this theater and all these musicals and 100 years of history, and all these gay men are involved — it helped me feel like I found a place for me.”

Guest studied theater at Kennesaw State University but dropped out before graduating. He headed to Atlanta, where he spent years working as an actor.

“I was getting to the top of the totem pole in Atlanta theater,” he said, “and I was 24 and had been doing it there since I was 19. I needed some more push.”

That summer, Guest visited Chicago for the first time. He loved the city and moved here in 2015. But after arriving, acting roles dried up.

“I didn’t work for three years, and I thought I had made the biggest mistake of my life,” Guest said. He supported himself with a job at a coffee shop in Lake View.

It was during this gap that Guest leaned into writing. "At the Wake of a Dead Drag Queen" was his first script, and he based it on his uncle Anthony, the first family member he had known who was gay.

“In 2005, he sat me down and he told me that he was gay,” Guest recalled. “I remember being like, ‘Oh, my God, this is amazing.’ And then he told me, right after that, that he had AIDS, and that just was very confusing and painful for me. I was 15 and I was still in the closet at the time.”

Anthony, who actually performed under the drag name Courtney Berringers in rural Georgia, died months after the conversation. While he never got to witness his uncle’s drag performances, Guest used his own life and experiences to fill in blanks in the script.

“I was writing it, always knowing that I would play it,” he said, “but I did not necessarily know or think that there would be a production of it.”

Guest workshopped his pages in Chicago, reading them at local open-mic nights and graduating to self-produced full readings around town by 2018.

By chance, Paul Michael Thomson, a governing artistic ensemble member at The Story Theatre, saw a reading. Thomson encouraged Guest to apply for the company's emerging playwright residency.

“I thought that it was unlike anything that I’d seen before,” said Thomson. “It reminded me of Tennessee Williams and the memory-play tradition in American theater, but done with a new cast of characters and centering a new story.” Guest landed the residency and The Story staged the world premiere of the play a year later.

Whitney Houston ballads, a love story and humor throughout

Thomson said he admires the depth of the story.

“One of the things that this play is about is how Terry’s character and my character both have HIV,” said Thomson, who is white. “But our access to treatment is so much different because of our racial identity, because of our class identity.” That distinct reality becomes a plot point in the production.

The show's director, Mikael Burke, said Guest has a keen ability to discuss heavy topics in his writing that still translate to enjoyable stage plays. There are Whitney Houston ballads, a love story and humor throughout.

“[Guest] writes stories about people who are real and going through experiences that are true,” said Burke. But he’s also not afraid to be “playful and imaginative.”

Now, at 35, Guest is the same age as his uncle Anthony when he died. This time around, he is approaching the role with a fresh perspective, and more experience. He’s tightened the script and will be joined by the actor and director from the original production, all of whom have become friends over the years. But the work, he says, still “sounds like an Anita Baker song if you’ve been smoking cigarettes on the front porch all night on a hot summer evening, with a little bit of whiskey.”

For its creator, the play not only speaks about his own life and his uncle’s; it also speaks to society at large.

“In the very first version of this play, there was an epilogue that talked about how the president had removed funds from the CDC and with their HIV and AIDS research,” said Guest. He was writing this around 2016, and eventually, the HIV/AIDS funding was spared. He was relieved at the time to cut the epilogue, as it was no longer relevant. Now it is.