Backstage at the Miss Continental pageant in 1992, Mimi Marks was panicking.
All around her, contestants were pinning their hair up for the evening gown competition. But behind her, Kim Cleveland was doing the opposite—setting Marks’ hair in rollers and letting it fall down.
There were no mirrors nearby, so Marks couldn’t even see what Cleveland was creating.
“What are we doing?” Marks kept asking.
Cleveland didn’t hesitate.
“Bitch, just trust me,” she said.
Moments later, Marks stepped onstage—and took the crown.
Cleveland, a revered hair- and makeup-artist in Chicago’s drag and transgender pageant scenes, spent decades shaping the looks—and often the careers—of some of the city’s most celebrated performers. Known for her instinct and creativity, she worked behind the scenes to help define an era of pageantry that would inspire generations of artists.
Cleveland died March 17 at age 65, just two weeks shy of her 66th birthday, according to Marks.
Born in Hawaii, Cleveland moved to Chicago as a child and built her life and career in the city, eventually becoming a central figure in its pageant community.
She spent much of her career at The Baton, a long-running Chicago drag club and incubator for pageantry talent, where she worked in nearly every role—from bartending and waitressing to lighting and sound—while honing her craft as a hair and makeup artist.
By the late 1980s and early 1990s, Cleveland had become a sought-after creative force behind the scenes of major competitions, including Miss Continental, where her work helped define the look of an era.
For performers like Marks, Cleveland was more than a stylist—she was a collaborator, mentor and creative director.
“I would literally not be Mimi Marks, the person I am today, had it not been for Kim,” Marks told Windy City Times.
The architect behind the crown
Marks said Cleveland’s instinct—and her insistence on trust—defined how she worked.
That trust paid off the night Marks won Miss Continental. After stepping onstage and seeing the finished look for the first time, Marks said everything clicked.
“I felt like I was walking out of an old Hollywood movie,” Marks said. “Kim knew exactly what she was doing.”
Marks described Cleveland as not just a stylist, but a creative partner who helped shape entire performances.
“Kim produced me,” Marks said. “Everything I did from that point on—she was there with me.”
For Cezanne, who moved to Chicago in the early 1990s and joined The Baton’s cast, Cleveland played a similar role during a formative period in her career.
“Kim was behind my first photoshoots, my hair, my makeup—everything,” Cezanne said, recalling how Cleveland helped her refine her signature look as she developed her stage presence. “She was a big contributor to what the kids now call my brand.”
Cleveland’s approach was often intuitive, Cezanne said. Rather than arriving with a fixed plan, Cleveland would build a look in real time.
“You really had to trust her,” Cezanne said. “I don’t think she always knew exactly what she was going to do until she sat down in front of you.”
That spontaneity often translated into bold, ahead-of-the-curve choices. When Cezanne competed—and won—in Miss Continental in 1994, Cleveland created a dramatic, voluminous hairstyle that stood out at a time when pageant looks were more uniform.
“Kim was always ahead of her time,” Cezanne said. “Very fashion-forward before it became trendy.”
Backstage, Cleveland was known for her calm, focused presence. While others moved around or watched performances from the wings, she stayed with the person in her chair, fully locked in on the task at hand.
“She wasn’t running out to see what you looked like onstage,” Marks said. “She sat there and made sure you had everything you needed. That’s what she was there to do.”
More than a hair and makeup artist
Cleveland’s talents extended far beyond the chair. Marks described her as a multidisciplinary artist who could draw, design, cook and create with equal ease.
Cleveland studied art as a young person and maintained a sharp eye for color, texture and composition throughout her life—skills that translated seamlessly into her work in beauty, Marks said.
“She could do everything,” Marks said. “She was an amazing artist.”
That creativity showed up not only in pageantry, but across a wide range of professional work. Over the years, Cleveland did makeup for television and high-profile clients, including a stint working on the “Vibe” TV show and time on tour with singer Patti LaBelle.
Cleveland also styled weddings and events, bringing the same level of care and precision to clients outside the drag and pageant worlds.
Even with that range, those closest to her said Cleveland was most comfortable working behind the scenes, focused less on recognition than on getting the work right.
“She never wanted to be in the spotlight,” Marks said. “She was like, ‘I’ll do your hair, I’ll do your makeup—I’ll do whatever—but I don’t want to be in front.’”
Outside of work, Cleveland was known for her humor, her love of music and her deep friendships. She introduced friends to new artists, collected albums and made rituals out of shared moments—whether that meant late-night conversations, watching fashion shows or making meals together after performances.
For Cezanne, those quieter moments were just as defining as Cleveland’s work backstage.
“We would just sit and talk for hours,” Cezanne said. “She loved music and old movies. We had a lot of fun.”
A legacy carried forward
For Precious Brady-Davis, Cleveland’s impact extended far beyond the stage.
Brady-Davis worked with Cleveland while preparing for her wedding, seeking out what she described as “the best of the best” to do her hair and makeup. Cleveland created an experience that felt intentional, calming and deeply personal, Brady-Davis said.
“She would have me lay on the floor,” Brady-Davis said. “It was like a meditation. She didn’t want beauty to hurt—she wanted it to feel soft.”
Cleveland’s approach was rooted in both precision and care, Brady-Davis said. She was known for her ability to work across skin tones and styles, often mixing colors to find the right shade long before broader conversations about inclusivity in beauty became more common.
“There was a grace about it,” Brady-Davis said. “She really wanted to highlight your features and make you feel beautiful.”
But Cleveland’s influence also lives on in the generations of performers and artists who followed her.
Many who work in hair and makeup today, Marks said, point to Cleveland as a direct inspiration—someone who showed what was possible behind the scenes and set a standard for both artistry and professionalism.
“I know people who do this work now because of Kim,” Marks said.
For Brady-Davis, that legacy carries particular weight as a transgender woman navigating a path shaped by those who came before her.
“I got to be because of people like Kim,” she said. “With her goes so much history—but it’s our responsibility to carry that forward.”
A celebration of Cleveland’s life will be held May 3 from 1-3 p.m. at the Center on Halsted, 3656 N. Halsted St.
