Chilli Pepper. Image from Windy City Times archives
Chilli Pepper. Image from Windy City Times archives

Miss Gay Chicago 1974, the first Miss Continental in 1980, and a top draw at the Baton Show Lounge for decades. Chilli Pepper was a legend. Social media was filled with tributes to Chilli September 11 as news of her death spread quickly across the globe.

Update: A celebration of life/memorial service, with visitation 11 a.m. to 1 p.m. followed by an inurnment service, will take place Oct. 5 in May Chapel, on the grounds of Rosehill Cemetery, 5800 N. Ravenswood Ave. A reception will follow.

Chilli Pepper at the Who's That Girl benefit in May 2024. Photo by Tracy Baim
Chilli Pepper at the Who’s That Girl benefit in May 2024. Photo by Tracy Baim
Chilli Pepper. Image from Windy City Times
Chilli Pepper. Image from Windy City Times

This is a developing story and we will have more news soon.

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 chili pepper. I blushed and took the name.” Though Chilli always made it very clear that her name had two L’s and not one.

Upon coming to Chicago, Pepper soon won the Miss Gay Chicago title in 1974 and remained here. She was working at the Blue Dahlia on North Avenue when Baton owner Jim Flint cajoled her into moving to the Baton where she remained a top draw for decades. At the Baton, Pepper flourished, saying “Thanks to Felicia [Baton owner Jim Flint], I am allowed to create my own personality onstage. All of us at the Baton do this. Felicia has always been wonderful at allowing each of us that creative freedom—and it works.” 

Pepper likened her stage persona to Joan Collins on Dynasty: “It took me a long time to create this cartoon. It’s a cartoon that works for me.” Chilli’s act was pantomime, but her stage work was closer to improv and performance art. “I make faces and interact to get a reaction. If I try to be glamorous, or flirt or be mean, I am looking for a reaction. Not everyone understands this, not everyone has the same sense of humor. I like to be an artist. The people who understand me enjoy it because they see what I am doing. It would be nice if we just have to look good, but there is more to it. There is art. And it is an art where we have to jump up and down in high heels. It is what it is.” 

Pepper frequently did numbers by Millie Jackson. “She is probably my very favorite.” One of the biggest compliments Chilli ever received was from Jackson herself. “She had me open a concert for her once, and afterwards she said, ‘When I was watching you, I forgot that it was my voice.’” 

Video interview with Chilli Pepper by Emmanuel Garcia: https://youtu.be/RaN-mgsPQrM?si=-ViSvD33lbUOMXWk.

Chilli Pepper’s fame extended far beyond the gay papers. Her 2007 induction biography into the Chicago LGBT Hall of Fame bio reads, “Chilli was one of the first local media personalities to take up the issue of AIDS awareness, helping to bring HIV/AIDS into the homes of Middle America… .” 

At the request of Donna Karan, Chilli Pepper modeled as a mannequin in the main display window at the launch party of Barneys New York’s Chicago store. The event benefited the Design Industries Foundation Fighting AIDS (DIFFA). In 1979, when Michael Butler premiered the movie Hair in Chicago, Chilli was the ‘Premiere Entertainment’ and introduced drag to an audience who may have thought ‘drag’ applied only to car racing or having a bad day.” 

Miss Chilli Pepper 1981. With Andrea Nicole and Dena Jacobs. Windy City Times archives
Miss Chilli Pepper 1980, Andrea. Nicole. Dena Jacobs. Windy City Times archives

Her name was featured in gossip and “about town” columns in the Sun-Times, the Tribune, and even in People magazine. Pepper made frequent TV appearances on talk shows—Phil Donahue, Oprah Winfrey (a friend), Joan Rivers, and Jerry Springer shows. Pepper even had a usual booth at the Pump Room.

“The crowd is the best part of this job,” said Pepper in an interview a dozen years ago. “A woman came in a few months ago and said, ‘Do you remember me?’ and I said I didn’t, but she said she had come in with her mother about a month ago. Of course, my next question was, ‘How is she doing?” She said her mother had passed away a couple weeks ago. The woman added, ‘But I had to come back and say thank you, because you posed for pictures with her and that made her so happy.’ Those things are the biggest compliments. See, so sometimes they give me money and sometimes they leave me with something else. Those are the best tips.” 

Pepper admitted her “cartoon,” as Chilli called her persona, “can be a little rough around the edges. Not everyone can be Julie Andrews, but deep down I am a good and a kind person. People don’t want everything nice. I have fun. Not everyone understands, not everyone sees beyond the cartoon.” 

“How much of Chilli is me and how much is creation depends on who is watching and what they bring out in me. If you are interested in knowing me, you get me. If you only want the cartoon you see onstage, that is what you get. 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. This is what I use,” she said, gesturing to her face, “I make an expression and I see how they react. When I see people respond, then I know where to go. That’s how you perform. 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.” 

More news and reactions will be posted soon.

Chilli Pepper. Image from Windy City Times
Baton cast, including Chilli Pepper. Image from Windy City Times