Photo by Chelsea Ross. 

Trans Performer Chilli Pepper: What I Learned from Decades of Entertaining

Chicago's iconic Chilli Pepper reflects on winning trans beauty pageants and appearing on sensational talk shows in the 80s, and the three decades she's spent performing at legendary clubs like The Baton.

This interview is part of Broadly's Trans Legends oral history project. Read more here.

As an adolescent coming of age in the 80s and 90s, some of the first trans people I saw were on TV talk shows. Indicative of the ignorance of the time, the episodes featuring transgender guests had titles like, “Guess what… I’m a man,” “My Boyfriend is a Girl,” “Sexy, Hot Ladies… Or Are They?,” and “Men Living as Women.”


The trans folks appearing in those shows, many of whom are still active in our communities today, brought boundless integrity to exploitative set-ups and salacious reveals. Among this canon of legends is the irreverent Chilli Pepper, who appeared on Jerry Springer saying, “[I just] blend right in into society, and not because I’m trying to hide anything or anything else, it’s just that I have to deal with myself when I look into a mirror so it doesn’t matter what anyone else thinks.”

Appearing on TV shows such as Oprah, Jenny Jones, Donahue, Joan Rivers, and many more, Chilli Pepper was one of the first public figures raising awareness about the HIV/AIDS epidemic at a time when President Ronald Reagan, and much of the country, were ignoring it. In a public conversation at Little Village in Chicago in 2013, Chilli remembered: “You were seeing people who were dying, and a lot of people weren’t doing anything because they didn’t understand what was happening. People were dying all around you, and they were dying very quickly. I was blessed by having lots of media exposure. The media has such big power… if you don’t say it, nobody else is going to say it.”

Although notoriously secretive about her origins, Chilli has roots in Santiago, Chile. She became Miss Chicago of 1974 and in 1980 was crowned the first ever Miss Continental—top honors in the world of transgender pageantry. Known more widely at the time as “female impersonator” or “drag” contests, trans pageants are an anchoring tradition consistent throughout transgender history, dating back to the late 19th century in the US and earlier in Europe and Mexico. Soon after her win, Chilli began performing for a few years as a headliner at The Blue Dahlia show lounge in Chicago and later joined the cast of performers at the city’s legendary Baton Nightclub, established in 1969, where she still graces the stage with rousing choreography and lip-synced renditions of dance club hits.


Chilli Pepper presenting the crown to Miss Continental 1982.

Chilli’s iconic on-stage persona, which she refers to as her “cartoon,” is soulful, unapologetic, and disinterested in anyone else’s judgement. In 2015, I encountered the electrifying presence of Chilli Pepper in the flesh for the first time the same way millions of people before me discovered her: on the stage at the Baton Nightclub. Living up to her name, she looked to be on fire, pantomiming, shifting through emotions. Her fluid movements seductive and self-possessed––an artist in her zone.

In Jim Flint: The Boy From Peoria, author Baim Keehnen quotes Chilli analyzing 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. This,” gesturing to her face, “this 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.”

For those in the LGBTQ Chicago nightlife universe, Chilli is the penultimate star, famous for her ostentatious jewelry and impeccable style. But while speaking with Chilli, I was struck by her deep tranquility and reflection, as well as her reverence for fellow performers at the Baton, past and present. She veered from dwelling on the past in favor of ruminating on the nature of performance and how trans lives have always managed to thrive on the margins.


Chilli’s look has evolved over the decades, but I have the closest affinity to her style of the 80s, which can be appreciated in archived videos such as this one. She was the showgirl of my childhood dreams: hair short and sassy like a red-headed Pat Benatar, and decked out like a glitzy Dynasty character. She seemed to effortlessly manifest her own liberation, mouthing prophetic words sung by someone else, and making them appear as effortless and graceful as second nature:

Yes, I'm a liberated woman
But that shouldn't make you be so cold
I can't let you use me
I've been around the world and back again…
So you ain't talking to no fool

Interview has been edited and condensed.

You're the winner of the first Miss Continental Pageant in 1980. What was that like? What led you to that moment?

You're making me think really back… I had seen a pageant a month before in Florida, Miss Florida. My employer, Jim Flint, was there too, and I think that’s where he got the idea to do Miss Continental. Because Florida was before Miss Continental. It was a terrific, terrific, spectacular pageant. The most visual centerpiece.

Did you live in Florida?

No, no, no, but I went. I used to go because I had friends who had a very large club there, the Copacabana. They sponsored me to enter Miss Continental. They had a lot of very large clubs—in Key West, Fort Lauderdale, New York, Fire Island. The Fort Lauderdale club, maybe on a good Saturday night, could have up to 5,000 to 6,000 people. For many years, that was probably the most fabulous club in Fort Lauderdale. People came from all over the world to go, and they would go to Fort Lauderdale, that's where they would go hang out. It was a destination; when Barry Manilow sang that song “At the Copa,” that's what he meant.


Did you call yourself “female impersonators” at the time? What was the language you were using?

I don't think [we used the term] “trans,” I don't even know what that means to some people… they would just really say “impersonators.” They didn't use “trans;” a lot of people misunderstand that word. “Trans,” for what I thought, was when you already had your, you know, your surgery and you were really female. They were pre-op transsexuals. What they used to say when anybody would ask what you were if they were what they were, they would say, "We are pre-op transsexuals." Otherwise, they would assume that you were completely done, and that could get you in trouble, because you were advertising or saying something that you were not. So if you were impersonating, that's one thing. Then when you're pre-op, you're on your way to whatever you're trying to achieve.

The girls in the pageants were showgirls and they weren't that interested in labeling themselves. You just were who you were and that was that. I don't think they were walking around saying, "I'm pre-op this or post-op that or I'm a female impersonator." They were just doing their thing and doing pageants and having fun.


Courtesy of Marc Reboy.

How did you find your way to The Baton?

Well, after I won Continental, I got the offer to join the cast. It was interesting, because previous to me getting there, they had two or three previous casts. I didn't know those girls.


How did the pageants change over the years?

Unfortunately, it used to be a little more really about [talent]. It wasn't about who had the bigger breasts and who had the bigger hips and who had the bigger all that. It was really, literally a performance. But it was a different musical time. It was different audiences. So the audiences would really appreciate what music you did for the value of what you were doing as a performance.

It's changed because now, for some, they think that talent has changed or they thought that you basically show[ed] your body and that made you more talented, it made you more interesting. Because they were amazed that you had breasts and they were amazed that you had some work done and you had hips and rear ends and all that. So, it's a more visual thing. The whole thing is supposed to be a little bit about everything. It's not about, I'll show you my breasts, or, I'll show you a gorgeous dress. By the time you notice the dress, the number's over. You don't really know if the performer was engaging with you.

How much distance is there between the performance and real life?

I've seen people who really, their life is their performance. For me, my creation of my cartoon is always been a little bit more tougher and rougher and a little bitchier. But that's just my performance. Then people think that that's how you really are, but they've never taken the time to get to know me as a person. That's the unfortunate part about this business, or any kind of business. They know really nothing about me. They don't know that I also like to date, just like the rest of us. Indirectly, we're all in the same boat. We're just in different boats at different times and different arrivals and departures. They don't know you. I'm sure that you have that problem. They don't know who you are, what you are, how you think. And unfortunately, a lot of times, I think in any kind of situation—in straight or gay situations—they assume that whatever you're presenting for those four or five minutes or wherever you are, that that's how you are.


How did the girls get along with each other at the Baton back then?

I think that there was, believe it or not, more of a family. Now it's much more competitive. I tell you what, the friendships seemed a little more real. Now they're not. You know what I mean? Everybody has so much more on their plate, or they don't want to invest the time to do that. Now it's a different environment, they live differently, they have different agendas.

What do you think is contributing to those factors?

It could be whatever their life is like, and I don't know what their private life is. You know what I mean? Before they would share, you could tell a little bit, but now I don't know what they're going through and they don't know anything that I'm going through—not just me, just anybody. They're more competitive. They're just like, "I'm here to make a couple of dollars," and that's that. It's not as friendly, I think.


Photo by Chelsea Ross.

Do you feel like audiences have changed as well?

The audiences, they love what they love, or they like it or they don't. A good performance doesn't have to be [from] somebody who does everything that is new, it has to be different memories. All the audiences come to a show, of any kind, to see something that brings them memories, and hopefully good memories. A song that can touch your heart or your brain, that you heard 10 years ago, 20 years ago. It’s not about the new rap number that just came out, or the new dance number—which is cool too—and that's why it's supposed to be a show.


A lot of people who have shows, they think that the show's about them. The show's not about them, it's about the people who pay to see the show. It's not about what the staff think, and if they've seen it before—and they've seen it before! There's many shows, especially around the world, that do the same show, like a Broadway show. Meaning that the same performer does the same song with the same outfit—the same thing. I only want to please who came to see what I'm doing. You know what I mean? They've paid. The house already made their money, and they're drinking. Let me be the performer. A lot of times people suggest, "Oh, I've seen that before," and it could be one person who can disrupt other people's judgment and what we're doing. They have no idea, they've never done that before themselves, ever in their lives. "Oh, I've seen that dress." Well then, if you don't like that dress, you should buy me one and then I'll be more happy to put it on.

"Unfortunately, the ones that should say 'thank you' to you, they never do."

Chili Pepper is your art, she’s your creation.

That's my cartoon. Create a cartoon for the stage. That's what works for me. I can only be me. People try to change [that and suggest], oh, do this or do that. Well, I could, but it doesn't feel right. I know what works for the people that see me. They have to be people who see me, that like what I do, because I can't do what Mimi (Marks) or Sheri (Payne) or Chanté (Alexandra Billings) or any of those girls do.


I know that you've opened the door for Chanté, for Mimi; they often credit you for giving them their first job, for giving them their first break, for being a mother figure. I mean, you walked Chanté down the aisle in her mother’s absence…

I'm not trying to be Mother Teresa…. I think that, if you can do something nice for somebody … you hope, in your lifetime, that you would have had someone who would have done the same for you.

For me, I kind of came and I didn't know anyone, nobody cared. I don't mean that in a bad way, so don't think that. You start creating and building. [But] I had no famous friends or any kind of fame or any kind of recognition. For me, I've been very lucky to meet audiences, and through the audiences, that's how you meet whatever your journey's going to [bring] you. Sometimes it's hard, it's not an easy thing. It's not a lucrative thing, and it's absolutely never easy. We make it look easy. We make it look easy because that's what we do. It's not.


Courtesy of Marc Reboy.

What was it like appearing on talk shows in the 80s?

The smartest ones were Donahue and Oprah, they were asking more questions. Other hosts had no knowledge of anything. When you went on a talk show, the audience would ask questions, and you never knew where they were going to take you. The most asked question was, “What bathroom do you use?” When you’re going to the bathroom, you’re not concerned with other people, I’m not going there for any other reason. They don’t do that as much now. As the years have progressed, they’re much more aware of what’s going on, and much more sympathetic. The hosts know the answers to the questions now. They weren't trying to be shitty back then, they just didn't know any better. You couldn’t take too much offense to that. More intellectual people would ask more sensitively. In reality, they're all just curious. And the ones who didn’t ask were too embarrassed or didn’t want to hurt your feelings.


A lot of shows now, you might notice, don’t allow their audiences to ask questions anymore. They’re afraid of what you might say. It’s not any different––at least when they were asking, they had a chance to ask. Or they were asking questions that maybe the host didn’t want to ask, because [the host was] too polite to ask, didn’t want to step on your toes.

What are some of the things that have gotten you through the hard times?

Biting my tongue and knowing that I have to pay rent. Fame is very funny, you know, because you can have great fame, but when I get in a taxi, nobody cares about my fame. When I go to the grocery store to buy a tomato, nobody cares about my fame. They don't even know that I have fame. They say, "Okay, pay for the tomato."

Unfortunately, the ones that should say “thank you” to you, they never do. I just think that sometimes, unfortunately, our own kind—not all of them, but the very small amount… we all have our own bullies. You know what I'm talking about.


Courtesy Paul Escriva.

This is a theme that is coming up in a lot of my conversations—that we all have our own bullies.

We do. That's kind of unfortunate. I can only speak for me. A lot of people, they're a little sharp with their tongue. By that I mean, they'll say, "Oh, girl, I've seen that dress before,” and, “I've seen those shoes." That's hurtful to people. And that's a form of bullying. And maybe I've done it, too. Maybe in jest sometimes. There are a lot of other people who just do that all the time without even knowing that they're hurting you. When we talk to each other a lot of times, we think others are immune to being sensitive inside, because we all try to present ourselves tougher.


Do you think that that has changed over the years?

I think it's gotten worse … because it's a different generation. And because it's a little easier to do, they can say anything they want to at any time. Not only in our group, because that's allowing other people anywhere on the street in mid-America to say anything they want to if they choose to say it to you, 'cause now there's so much bitterness that they just can say anything they want to.

"That's all you can ask for: to be allowed to live whatever your show is until the music stops."

Yeah, it's no longer just something that you're saying to your friend, it's something that you're saying to the world.

Right. You didn't hear that years ago. I mean, it happened, [but] very rarely. But in general now, there's so many angry people. Sometimes, they get worse. Some people, with time, they get better, because they start to learn and to tolerate. And it goes into––hopefully––patience, and then they're okay. They learn about themselves. If you learn something about yourself, then maybe you'll leave somebody else alone. I can’t make anyone happy unless you want to make yourself happy. I’m trying to, by jumping up and down, and miming, and dancing, but if that doesn’t work, I can’t do more than that. I can only do what I’m capable of doing.

I'm wondering, for all of those young people who are struggling and now living in a world where there's more anger and more vitriol, what would you say to some of those young people?

What you have to do is just make good friends and really be loyal. Don't have any envy or anything. Because everybody has their own star above them. They can achieve things and be happy for somebody else. They have to just try to be kind, just trying to make it better for yourself and for the ones who come after you. That's all that you can do, really.

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If you're just kind and trying to put all that other stuff aside and just be friends and try[ing] to keep a really peaceful life, it could be really gorgeous. For us, from the people who came before any of us, it was even tougher. They made it gorgeous for us. They passed it on, we just don't know how much of it gets passed on. We're not aware of that. But I'm sure, for their time, they were going through a lot of heartaches and all that, trying to be who they are. As time goes on, hopefully people or just this earth will let you be who you are. That's all you can ask for. That's all you can ask for: to be allowed to live whatever your show is until the music stops.

Then I guess I don't know, because I don't know what happens after the music stops. I hope it's pleasant for the next; I hope it's pleasant for me; and I hope it's pleasant if I come back, so I can really see it. It's whatever you believe. I mean, it is just a journey.