Growing up, Terry Guest dreamed of becoming Whitney Houston. “A well-dressed, gorgeous, singing-and-acting diva beloved by all,” he says matter-of-factly. Then, in middle school, around the same time Guest realized his dream might be hard to achieve, he took a musical theater class. “It all clicked,” he recalls. “I could utilize my interests in a practical sense.”

Guest, 34, might not be Whitney, but he has emerged as one of Chicago theater’s most compelling multihyphenates — an actor-director-playwright whose work is gaining national traction. Oak, his Southern gothic horror play, finished a successful run in Sarasota, Florida, last year and will be staged in Indianapolis and Buffalo before debuting in Chicago this fall as part of the National New Play Network’s Rolling World Premiere program. Meanwhile, his adaptation of Milo Imagines the World for Chicago Children’s Theatre is touring to Minneapolis and Omaha.

Drawn by Chicago’s vibrant theater scene, Guest moved here nine years ago from Atlanta to further his acting career. But breaking in wasn’t easy: He went three years without landing a single gig. So he turned to writing and began self-producing readings of his work. His breakthrough came in 2019 with At the Wake of a Dead Drag Queen, a play he wrote, produced, and starred in for the Story Theatre. “That play was deeply personal and incredibly scary to share,” Guest says. “But it also felt like the moment I could show people what I had to offer as both an artist and a writer.”

Now a three-time Jeff Award winner, Guest blends historical fiction with ancestral imagination, offering fresh perspectives on overlooked stories. “I find myself most interested in reimagining where Black and queer people fit into American history.” Next up: He’s under commission at Goodman Theatre to write Nightbirds, a musical inspired by William Dorsey Swann, a Reconstruction-era Black drag queen. Says Guest: “I have more stories to tell than I have time.”