For three decades, Murray Hill has captivated audiences around the world as a successful entertainer and actor. Sometimes referred to as “Mr. Showbiz,” this award-winning trans comedian—and now author— blends camp with a cabaret-style live act that fans can see in person at The Den Theatre, 1331 N. Milwaukee Ave., on Sunday, Nov. 1.
The Chicago appearance is a return to the Midwest for Hill, after starring as Fred Rococo in the queer-centered HBO TV show Somebody Somewhere. The series was set in Manhattan, Kansas, but in reality scenes were shot locally in Lockport, Warrenville, Lemont and Naperville.
Hill last visited the Windy City in September to attend the after-party for Crowned: Stonewall Sports Chicago’s All-Gender Pageant Fundraiser at Roscoe’s Tavern. He recalled, “It was packed in there. It was literally 15 drag queens and me. They were doing lip synchs, so I got up there to sing Frank Sinatra’s “My Way,” and people gave me cash for charity.”
His first book, Showbiz! My Life as a Middle-Aged Man, launched Oct. 6 with endorsements from high-profilers like Amy Sedaris, Sarah Jessica Parker, Margaret Cho, Ada Calhoun and Kathleen Hanna. Hill joked, “I made them do it. I will be cleaning their summerhouse swimming pools for the rest of my life, but their quotes are great.”
He was inspired by Tina Turner’s memoir, I, Tina, as he wrote the book. He called Showbiz “the origin story of Murray Hill. I tried to keep it focused on that. When I got offstage to think about my life, all of the challenges and bad things that happened to me are related to how I am now.”
Hill named himself after a New York City neighborhood where he lived and sought refuge in the nightlife scene. Thinking back on his early life, he reflected, “I became a drag persona in the ‘90s, when everyone came to New York to reinvent themselves. In the queer community, no one asks about your dead name or what your childhood was like. How you presented was how you were, and there was a real safety in that.”
He earned early success in the John Cameron Mitchell film Shortbus and two television series followed in 2010, Gravity on Starz and Bored to Death on HBO, the latter network ultimately being home to Somebody Somewhere.
Hill mused, “I grew up watching HBO, and Sundays were the holy grail of television. The joy we found in Somebody Somewhere was that we were able to be our authentic selves. We were let into the mainstream club by the gatekeepers and we were able to hang out for three seasons before they sent us home.”
During its run, Somebody Somewhere won a Peabody Award; a Primetime Emmy Award for Jeff Hiller as Supporting Actor; and the main cast received an Ensemble Award at the Critics Choice Celebration of LGBTQ+ Cinema & Television. Hill earned a Trailblazer Queerty Award in 2025 as well.
Composing his thoughts while on comedy tours proved challenging for Hill. He required a quiet space to focus, so Showbiz took over three years to complete. Not everything made the final version of the book either. He was disappointed it lost a section on Real Housewives of New York City’s Countess Luann de Lesseps, for example.
“They cut it because I went on too long,” he said. Hill went on the road with the Countess and he recalled her particularly raucous 2019 Chicago appearance: “That sold-out show at the legendary Chicago Theatre was insane and I will never forget it. She walked out onstage like she was Judy Garland and the room was full of gay guys.”
Hill wants Showbiz to function as a “survival story” that can help others. He said, “I want people to know that you can grow up as a tomboy in a religious house and go through traumatic things, but when you come up on the other side, you can be a positive force. A person shouldn’t repeat the hatred and bigotry they experienced, but go towards the light.”
Another impetus for the book was raising visibility: “I want people to understand that queer and trans people are just like everyone else,” Hill explained. “We have the same problems and challenges. We are humans. We have a heart. Let’s connect that way.”
He added, “I am a senior now. Drag kings, trans men, lesbians, butch, femme, masc- all of the words we have now- are still not equal in our own community or in society. I am still fighting the fight and I am finally the age of my character.”
He further joked that he’d like to see Elliot Page play him in a movie version of Showbiz, adding, “Well, maybe if I went on a GLP-1.”
Hill admitted that he is “not completely over some of my immediate family trauma and I still have to work on it.” But he also expressed gratitude for much in his world: “I have an incredible wife. I am an uncle to three beautiful boys, and I have amazing friends. I made it out and I am surrounded by love now.”
See Murray Hill and Chicago drag king opener Tenderoni at 1331 N. Milwaukee Ave. on Nov. 1, starting at 7:15 p.m. Find tickets at thedentheatre.com or mistershowbiz.com To purchase Showbiz! My Life as a Middle-Aged Man, visit here. Inside the book, Hill includes information on resources such as translifeline.org, thetrevorproject.org and rainn.org, among other organizations.