Iconic performance artist and LGBTQ+ and HIV/AIDS activist Chilli Pepper died surrounded by close friends at her Gold Coast neighborhood apartment on Sept. 11 after a years-long battle with colon cancer.
When asked about her life outside of her performance and activist work, Chilli was elusive about details such as her date of birth and given name, although it has been reported that she grew up in Detroit.
Her over 50-year career began when she first came to Chicago as a teenager and performed at an impersonator contest at Park West, when she could not even get into bars legally, a fact that organizers never discovered. In more than one interview, she called herself a “female impersonator” and not a “drag queen.”
A legacy of activism
In the early days of the HIV/AIDS pandemic, Chilli was one of a small handful of people who brought awareness of the disease to a wider audience on nationally syndicated talk shows hosted by Oprah Winfrey and the late Phil Donahue, Jerry Springer and Joan Rivers, among others, as well as in publications like People and Playboy. She also talked about HIV/AIDS in local interviews with WGN-TV and was mentioned in the Chicago Tribune’s “Tower Ticker” and “Inc.” sections, Irv Kupcinet and Candace Jordan’s columns in the Chicago Sun-Times and Skyline newspaper.
Her closest friend, Steven Feinstein, passed away from AIDS on May 28, 1992, at age 34, which affected her deeply.
Chilli and others in the drag community might not have been ordinarily welcomed in many public spaces or mentioned in the mainstream media. She broke down those barriers and made it possible for performers like Alexandra Billings to aspire to other forms of entertainment media such as the TV show Transparent and Broadway appearances.
In a 2018 Vice interview, Chilli praised Donahue and Winfrey specifically, since they asked the smartest questions out of all the TV hosts whose shows she appeared on.
Chilli performed up until her March 22 cancer diagnosis at a number of Chicago venues, among them the now defunct The Blue Dahlia show lounge; the now-defunct The Bistro; and The Baton Show Lounge, first in Chicago’s River North and then, in recent years, Uptown neighborhoods. She also performed at other locales for LGBTQ+, HIV/AIDS and other community non-profit benefit events for many decades. Her final performance was for Howard Brown Health’s Who’s That Girl event in May 2024.
Creating an iconic persona
In their 2011 book, Jim Flint: The Boy From Peoria, authors Tracy Baim and Owen Keehnen included a quote from Chilli where she spoke about her own stage persona: “Any description of Chilli must come from the audience, from you. Chilli is a response. Chilli is a mirror. This is my art; this is what I use to perform. I’m not naked. That’s not what I’m selling. … [My face] is what I use. I make an expression and I see how they react. The key is seeing yourself through their eyes. If you judge me because you think I care about this or that, or judge me because of who I hang out with, I don’t care. It’s taken me years to get acceptance. That is going to be handed down to other people. That is another and maybe a larger way of being kind.”
Keehnen wrote in his own tribute to Chilli: “Her name came after a beach day in South America with a friend. ‘I was sunning and became very, very red. My companion told me I looked as red as a Chilli pepper. I blushed and took the name.’ Though Chilli always made it very clear that her name had two L’s and not one.”
Chilli said in a 2017 Chicago Magazine interview about herself, “I don’t have power. I don’t have money. You know what I do have? Fame.”
Chilli’s many accolades include Miss Gay Chicago 1974; The Baton Show Lounge’s Miss Continental contest of 1980 (she was the first winner to hold that title); and inductee into Chicago’s LGBT Hall of Fame in 2007.
The LGBT Hall of Fame’s biography of Chilli noted that Chilli likely introduced some mainstream audience members to drag at the 1979 Chicago premiere of the film adaptation of the musical Hair. Years later, when Donna Karan sought to make a statement at the Chicago Barney’s store launch party, she called on Chilli to model as a mannequin in the store’s main display window.
“Let them be showgirls”
In a Block Club Chicago interview in 2023, Chilli said of the drag bans in GOP-controlled states, “Let them be showgirls. [Others] should concern themselves with taking care of their children themselves. They should try to be nice human beings and do their own thing, and let other people do their thing.”
In March 2024, Chilli presented GLAAD’s Vanguard Award to her longtime friend Oprah Winfrey (they met two weeks after Winfrey arrived in Chicago and Chilli became her first friend in the city) for her years of allyship to the LGBTQ+ community. Winfrey personally requested that Chilli give her this award. In her speech, Winfrey joked about Chilli’s three-day journey by train from Chicago to Los Angeles to present her with the award because she had a fear of flying (and elevators).
Chilli was also known for her creature-of-habit ways. She had no driver’s license, computer or cell phone, and wore Chanel clothes most of the time. Chilli also loved jewelry, and specifically clip-on earrings.
Since Chilli’s death was announced, there has been an outpouring of remembrances from The Baton Show Lounge, the Chicago LGBT Hall of Fame, GLAAD, The Continental Pageantry System, U.S. House Rep. Robin Kelly and Illinois state Sen. Sarah Feigenholtz.
Chilli is survived by countless chosen family members and friends.
Longtime friends remember Chilli
Oprah Winfrey: “Chilli’s zest for life was mirrored in her mega-watt personality. She made me laugh a lot. She brought the Joy!”
Renowned chef and Common Threads founder Art Smith: “Chilli was more than an entertainer. We lost one of our greatest Ambassadors to Chicago. In her field, she was one of the foremost in America. A friend of Presidential families, talk show hosts, pop stars and Hollywood actors. Her infectious, irreverent personality with that smile and those jewels from many admirers was her calling card like no other.”
Fellow stage performer Alexandra Billings: “There are people who enter your life with a sound or a piece of music or a giant hiss and thud like a tree chopped down, crashing onto a house. There are some who enter peacefully like a thumbprint or a whisper. There are people who enter a life with packed suitcases, filled with rules or blueprints. And there are people who enter a life bought and sold, closed up and bricked in. And sometimes there are humans that enter into your life with all of these things compact and ready. So confusing and chaotic, they seem to swirl around you like a tornado, getting ready to catch air.
“That was Chilli Pepper … All of it was Chilli. I met Ms. Pepper in 1983. And I could swear the rotation of the world immediately paused and gleefully turned in the other direction. She sounded like Zsa Zsa Gabor filtered through Colleen Dewhurst. She could spout the word, ‘darling’ and add so many syllables and extra notes, you would have thought it was the overture to Gypsy.
“She wore diamonds on her diamonds. There was a gleam in her eye when she joked and that was constant. She was the queen of the one-liners. To which Joan Rivers happily admitted. To her face. She was Oprah’s buddy. She was famous at a time when trans women weren’t supposed to be famous. Before RuPaul. Before Divine. Before any of us understood what a transsexual was, Chilli was exploring the possibility of it all.
“She was present at the very crossroads of every moment I spent and could always point me in a direction that not only gave me a new account, it also brought clarity to such a degree that I forgot I was lost in the first place. She held me. She put out her hand and picked me up. She set me on my own two feet and reminded me to walk forward. She never gave me advice, but she constantly alluded to the truth. She called me a liar and a betrayer. She spotted my bullshit and my manipulation. She never let me forget that time. I lied to her. And I never did it again. She wagged her beat-red manicured finger at me in public and admonished me like any good mother. And when my own mother boycotted my wedding to the human I met in 1976 and fell in love with, Chilli offered to step in for her.
“And she did. She got me ready. Helped me pick out my wedding cake. She was the first person to see my wedding dress and she chastised anyone who came to our ceremony expecting performance. In a time when family was obtuse, Chilli became true. At a time when I was left for dead, kicked out, told to stay away and blocked off Chilli took me in. She gave me space and when I fell apart, weeping in a puddle and curling up into a ball; she made sure I knew I had exactly 15 minutes before curtain.
“‘MY friend Chris.’ She would say. About my wife. About Chrisanne. ‘MYyy friend Chris, ..and my love.’ She would add. She loved love and she hunted it for decades. She simply couldn’t find the human who could side step her fame and still have enough space to romance her heart. She wanted to go to the movies and out to dinner, but the men in her life wanted to be seen going to the movies and out to dinner. When I was in doubt about Chrisanne, Chilli took me into her dressing room with her sequins and chiffon and her thousands of shoes worth thousands of dollars, and she said to me: ‘Mary, you have a love that is once in a lifetime. Don’t fuck it up by being a chickenshit. Love her right back.’
“We went for years without talking. And she would call me and I would forget, and I would call her back and there would be more time. The last phone conversation we ever had, the bravado and the ego and the character and the ear piercing horn blowing entrance that seem to bore itself in every room before she got near it; we’re gone. Disappeared. And she said to me in a very quiet and easy voice: ‘Shantel …’ her nickname for me for many years …’Shantel you know how I feel about you. Don’t ever forget how I feel.’ She took a deep breath, my eyes welded up on the other end of the phone and then she added with great aplomb: ‘ … and that you were felt by one of the greatest divas who ever lived!
“When I went to my dressing room that night I found a script on my table, neatly placed and centered. It was titled Vampire Lesbians of Sodom and it was written by the legendary Charles Busch. They had asked her to audition for it, but she had made a point to turn it down and hand it to me. I auditioned. I won the lead role. I left The Baton Show Lounge and I never went back. Chilli saw something in me that terrified me. She saw a future. And she abruptly made a left turn and sat down. She paused, held me one last time and kicked my ass out the front door. I absolutely believe without hesitation that my career would not have been remarkably close to what it has been, without Chilli Pepper and her guidance.
“There are people who have entered my life and have never left. And Chilli Pepper was blessed by a divine spirit and a revolutionary sense of history and change. She is the sound of every soul I have met that still leads me towards the newness. Her laugh echoes in me with her head thrown back and her diamonds sparkling in the night sky. To me, she was Mother. She was the sound of rebirth. She was the whisper of hope and the very pinnacle of faith. I’ll see you later, girl. And I have not forgotten what you told me … And I love you too.”
Fellow stage performer Maya Douglas: “I met Chilli Pepper 40 years ago this past Labor Day weekend. She instantly took a liking to me and we have been friends ever since. There are many stories and quips that I’ve gained over these past 40 years, but one thing is certain: She was an amazing person who was larger than life. If she liked you, she was loyal to a fault; if she didn’t, she wouldn’t waste her time on you. As ironic as it sounds, given her social notoriety, she couldn’t stand phony people. She could sniff them out instantly!
“We had a close friendship, especially when COVID hit; we spoke almost daily. She was happy when things slowly opened up again and we started performing again. I always picked her up and dropped her off before and after work. She confided in me about her health issues, which I kept close to me because she didn’t want it out there. Another important thing to know about Chilli was when I met her until her passing, she was 39 years old…always was, always will be!”
Longtime friend Cole Stolman: “The finest and most endearing aspect about my friendship with Chilli is that over the years, she unselfishly introduced me to so many gracious, interesting, supportive, hospitable and authentic individuals whom I now have the honor and privilege of calling my friends. Not only will Chilli always be the consummate showgirl, but she will also go down in history as the most generously loyal friend and connector of people.
“There was nothing more entertaining and amusingly vexing than a road trip with Chilli. Although she never obtained her driver’s license, she was the valedictorian of backseat driving, always telling you where to turn, when to speed up (never slow down) and ‘honk at this person’ while reaching for the horn herself. Whenever I or someone else would try to educate her on the rules of road, she never got tired of saying, ‘Shut up Mary, I used to drive a taxi’ (which is totally not true). I will miss my friend Chilli and those road trips very, very much.”
Longtime friend Tommy Segal: “Chilli was, in her own words, a showgirl. But that stage persona doesn’t capture the fullness of the person who was staunchly loyal and generous to a fault to her closest friends. Many of whom have been her friends for well over 45 years. Like Cary Fetman, celebrity stylist in L.A. of The Bachelor and Bachelorette, who used to live in Chicago and owned a store, Intrinisic, where everyone flocked to in the 80’s and 90’s for fashion forward outfits. I first met Chilli through Cary, at Intrinsic. And the two of them have remained close since the early 80’s. Chilli was equally comfortable all dressed up, “getting painted” as she called it, and going out to a fancy dinner, as she was being casual and watching TV and ordering Portillos. This she saved for her closest friends, and being one of those was like seeing behind the curtain of Oz, and finding that was the best treasure like no other, you knew you were in a place of true loyalty, as she was very protective of that space, and very generous to those of us lucky enough to be invited in.
Fellow stage performer Mimi Marks: “Chilli and I worked together for 25 years, five nights a week, three shows a night. She was so much more than a co-worker. We were family. She was my friend, my sister and sometimes even a mother! I will miss her greatly but I will remember all the most fabulous memories we shared together!”
Fellow stage performer Honey West: “No one worked a room like Chilli. She had the ability to take a song that someone else was singing and tell many stories to many different tables and groups of people and make it her own. I have never seen that before. The skill in which she worked a room and told her own story you would think she was singing the song live. She will always be remembered for her sense of humor, her wit and the way she could turn a phrase such as ‘Mary, I am the star of my own cartoon.’ Chilli knew who she was and how she orchestrated her own persona. I will always cherish the times I got to spend with her on a one to one basis and see the person behind the persona. I will miss her dearly.”
The Baton Show Lounge Owner Jim Flint: “Chilli was just like family to me. She was a superstar wherever she went in the United States. Chilli was also a trailblazer, there for the community and her fans were her life. She is gone but will never be forgotten.”
