Sheri Payne on Her 38 Years as a Trans Showgirl in Chicago

Read more from our Trans Legends oral history project, a growing archive of interviews with transgender icons and pioneers.

Sheri has been wowing audiences as a showgirl for more than 40 years. She has persistently shifted the conversation forward and evolved with the times, witnessing generations of trans femme and drag performers pass through The Baton, a “female impersonation” review in Chicago where she has worked since 1980.

I first discovered Sheri Payne’s magical presence on stage at the Baton where I saw her winning smile radiating warmth and acceptance over her adoring audience. Payne is a consummate entertainer, and, with a background in dance, her signature high kicks and full splits always elicit a frenzy of adulation.

Known for performing Whitney Houston hits for the duration of her years on stage, an archival YouTube video reveals Sheri commanding a brigade of back-up dancers in a Whitney Houston medley. Sheri’s talent jumps off the screen much in the same way it does when watching Houston, and her life parallels a similar trajectory to Houston’s—both having battled with substance abuse and been led astray by bad boys.

Sheri’s resilience has lived up to her mother’s words: “Your community of girls are the strongest people on the planet because you have the courage to be who you are. No matter what nobody else says.”

Interview has been edited and condensed for clarity.

ZACKARY DRUCKER: When did you start at the Baton?

SHERI PAYNE: I got hired in 1980. I graduated high school in ‘73. I was introduced to the Baton by my brother in ‘76. He took me there.

You’re from Chicago?

I'm born and raised here.

So, your brother took you to the Baton. What’d you think?

Well, he was my foster brother. I was most fascinated to the 20th power. My mouth dropped. I was into theater and dance and acting all through high school and a little bit in grammar school. Then we were introduced to the gay bars like after I graduated high school. There were a couple of gay bars right down the street from where I grew up, and they had shows. I was fascinated with those shows, but they were too cliquish. I was still too green. I wasn’t openly out. I was openly out as me, but I wasn’t out in high school or my first two years of college. I wasn't introduced to the gay scene until maybe two years into college.

What was that journey like?

It was fine for me. Everybody says New York is the trendsetter, but I think Chicago is the trend setter for everything. We’ve just always been outgoing and we always surpass the police. They can’t tell me what to do—we’ve always had that kind of mentality. As long as I ain’t breaking no rules or hurting nobody, you can’t tell me what to do. You can’t tell me how to live my life, you can’t tell me nothin’. You could throw me in jail, but the next day, I’d come right back out! We've got to be ourselves. Thank god we aren’t suppressed gays. I didn‘t hang out on the North Side until I was 21. Actually, in the 80s, it wasn't up North—there wasn’t no Boys Town, none of that. It was all downtown Chicago, right off the river. That's where the gay scene, the bookstores, the hookers, prostitutes, the straight guys that pick up the girls and the gay boys were. It was called “the stroll.”

Who brought you there?

My brother brought me to that area to see the show and then they would have guest nights on Sunday nights. That’s how most everybody got a job there.

I was already a performer. I had scholarships to Juilliard for dance, scholarships to Columbia. I could have gone all those routes. But here in Chicago, they let me dance as a girl and let me take classes as a girl, and they wouldn’t let me do that at Juilliard. I couldn’t believe it. But thank god they let me dance and transition. So I was transitioning in college. I thought I was going to be a math teacher. That didn't work out, but I'm very good at math. I taught math the first year at a catholic school in college as a substitute teacher. I worked at a bakery, and in retail. I have always had two jobs.

Once there’s a cast at the Baton, it’s really hard to get in. And the Baton had a hella fire cast in the early 80s. But one of the girls died, and a position became open. I hate that my sister had to die for me to get the position, but I was already there. She was way more beautiful and way more talented, because she had more experience. But that’s why I tell people, if you pursue a dream, you have to go for it. Those nights, I didn’t get paid. For like two years, I was there every Sunday night. But at the Baton, you could make tips. You got to meet people that you would never get to meet.

I got better and better, and then one day I got a paid booking for a Saturday night. I was working at Walgreens in the 1980s, and they had a deal where if you wanted to be a pharmacist, they’d send you to school. So I went to school to go be a pharmacist, and I got a call at break. They called my job at Walgreens! [Jim Flint, the owner of the Baton,] asked if I would like to have a job. It was right before Christmas. I ain’t looked back since, girl. I been there 38 years. Thirty-eight years! Twirling.

So who were some of the other legendary girls? Who inspired you the most?

Now Mimi [Marks] is the most beautiful blonde on the planet. I’m sorry, I love all my blonde sisters, but… There’s only one Marilyn, right? There’s only one Mimi Marks. She’s on caliber with Marilyn Monroe to me. There was another girl named Audrey Bryant. Six-foot-one. She was a Vogue model before this time. She looked like Lauren Bacall without the gap. Six feet tall, wore sandals, pedicured feet, pantyhose. You know, in the 80s, if you didn't have pantyhose on, you weren’t a lady. She would toss her hair in slow motion and it seemed like it would come back in slow motion to the right. She would look up with those baby blue eyes and sing her favorite song, a song called “Jealousy;” it’s the slowest song on the planet. They would be lined up around the corner! It’s hard to make them line up for a ballad!

There was another girl named Jan Howard. She did a lot of Bette Midler and Marilyn. And we had a girl named Jody Lee. [When you saw her,] you would’ve swore you were standing in front of Liza Minnelli, that's how powerful of an entertainer she was. And we had a choreographer name Peaches who never wore hair. She was like an Alvin Ailey dancer. And then they had a plus girl named Alotta Love—she looked like Victoria Paige and fit the bill of Felicia, [Jim Flint’s] plus girls.

That’s why I love Jim Flint: Jim Flint gave every girl on the planet a way to showcase herself. Most show-casters want this kind of girl or that kind of girl. He loves the variety of a variety show.

So that was the cast when I got there, and then the cast slowly turned Hawaiian. Jimmy went to Hawaii, fell in love with Hawaii, and found every showgirl in Hawaii he could hire and brought them back. It was everything that you could imagine because those girls, you know how they look—like the water just makes them beautiful, right? And then there were the times with Kelly Lauren, and Shanté [Alexandra Billings]… I’ve seen ‘em come and go, girl.

What changes have you seen at the Baton over the years? How do you think times have changed for trans girls?

I don't think it’s really changed much. That's my thing: Either you go all the way, or if you aren’t going to go all the way, just embrace who you are. When you meet someone, tell them! I tell them, you know, “I’m trans, I’m a queen.”

I was riding the bus one day, and one of my sisters got on the bus. [The other passengers] read her and she paid them really no attention. We don't care what you think. But they were hurtful, and that irritated me, because I was sitting there. I think they expected me to chime in, and when I did, I said, “You know you’re talking about me?” Girl, I think they lost their lunch!

They said, “What did you just say to me, ma'am?” I said, “Baby, you talking about her, you talking about me.” I said, “You talking about me because I'm one of those girls! You all sitting here belittling and making [us] feel awful. But we don't belittle you when you abuse your girlfriends, and cheat on your girlfriends, and don't pay your bills, and bring your girlfriends chlamydia, AIDS, and all that bullshit you tryin’ to put on us. You’re out here doing the same thing!” You know, it's ridiculous. Worry about yourself, and if you worry about the well being of others, it will be a better society.

Who were your heroes growing up?

My heroes, three: Leslie Rejeanné, Craig Cannon, and in the industry, Chilli Pepper. Leslie Rejeanné taught me how to be an entertainer. You gotta eat but the show comes first. If I put that first and think about my audience and they come out, they want to have a good time, they don’t want to see a diva. They want you to entertain them, period! That I'm the most beautiful; I got the prettiest body; they don't give a fuck about all that! They don’t. They want to be entertained.

Miss Chilli taught me that and how to get my look together. She was going to be interviewed by Oprah. I went to her house to get ready. I wasn’t going to be interviewed, but I wanted to be ready just in case. So I was getting ready. Chilli took a 15-minute shower, got her clothes on, maybe 10 minutes later, mama came out ready to go. And I was just trying to put a lash on. It literally took her 10 minutes to put her makeup on and she came out looking like Chilli Pepper. She said, “Put some lipstick on, finish putting your eyelash on, and we gotta go.” She said, “The more you do, the worse you’re gonna look.” I never thought of it like that. Your face is simple. So why are you making it complicated? And then she told me another thing: She said, “When you go out and perform, imagine the audience taking a shit.” You take your act lightly, you know?

What advice do you have for younger generations of trans people?

If you aren’t going to transition all the way, embrace your fishiness and keep on movin'! Be proud of the fact that people know you weren’t born as a girl. Nothing wrong with that! You should embrace it. I’m loving some of these young girls embracing the fact that they were born trans. That's who I am. So embrace this, stop running from it. I don't run from it.

You’ve got to bring the bully to the bully. If you want to harass me, you’ll get harassed. That’s what I do. It’s always the boys that tease me, chase me, that try to have me.

I’ve been bi. I had a female relationship in my forties. I didn't like it. I thought I would. She looked like a boy. I had so many bad relationships with men, and I was like, “I’m gonna try this.” It just didn’t work out sexually for me. I just can't get into it. You know, I have an open mind and I really could, but I like dick. And she found out she liked pussy. Know what I’m saying? Keep it blunt and grown up. We came to a realization because of that. We got to be true to ourselves.

Us girls, we’re more for straight men than we are for gay guys. We just got to be real about that. But then they need to be real, right?

Have you ever had a sticky situation with a guy where you felt unsafe?

Oh no, I only had one encounter, maybe 15 years ago. It was a guy who lived in my building with his wife and child. I'm a popular girl. My apartment was like a revolving door. All the kids, I'm doing pageants, the girls would come over, my daughter—and some of my kids are unclockable. And he’d invite himself over. I’d say, “Oh, you got a wife.” I don't know where the kids were. But he was cute! We had dinner, you know, then he thought he was going to go in the room with me, and I told him my dirt, and he didn’t even know! Every gay boy on the planet been to my house, and he sees this, since he's my neighbor. My gay daughters, you know, we've had talent out in the yard and stuff, and he still ain’t get the dirt that I’m a queen.

When I told him, we were sitting on the couch. He was rubbing on me. So I think maybe that he jumped and my daughter told me, “You know, that boy could beat you up.” I said, “Well now he will get his ass whooped but I thought he knew!”

That's the only time that's ever happened, where I didn't just tell the guy, and he found out like that. I was lucky that time, but from then on, I’ll tell a guy right away, you know, “Baby, I'm trans,” so they don't put two and two together when they look at me and I have to tell them again. They look at me and go, “Damn.” Some people go for it, some don’t.

I love my girlfriend Toni Valentina; she tells them when they see her right away, she says, “You know I’m a tranny?” as soon as they say, “hello.” That way it won't be a problem.

Do you think that it's more dangerous today?

I don’t think it’s more dangerous today; I think it's just a little more open because it’s the same game, different era. Be honest with somebody, then you ain’t gotta worry about it. No shame in the game. Yeah, a lot of times we find ourselves being hurt by being honest, but that's just part of life, too.

I never had trouble walking at night, sometimes gay boys made fun, but one night I got chased, and it did get serious. On 79th [Street], there was a McDonald’s and a funeral home. We walked past the funeral home, and there was like 20 boys at McDonalds and they said, “There they are!” There were seven of us, we were going to the gay club. They were like, “We’re gonna catch these motherfuckers and make them suck our dicks! And then we’re gonna beat their ass!”

Honey, me giving you head, how does that fit in with you whooping my ass? That’s some sick shit. I was 19. [I was with] kids under me in dance class. I was taking them to the gay club showing them the way. I told everybody to run. We scattered. Me and my brother hid in the dumpster. They wanted to beat us up and suck their dicks. That's an oxymoron, right?

Do you think you were too clockable as gay or as queer?

They knew. I mean they didn't know if I was a boy or girl, because I never grew facial hair. I barely have hair on my arms. So they would be like, “Is this a boy or a girl?” And then I worked in a clothing store in 8th grade when we were kids. You could work when you were in seventh and eighth grade. They had after school work programs. That’s why shit is so fucked up right now. The kids ain't got no work ethic. We was working at the after school programs at 10, 11, 12, 13 years old. We had jobs! Life was a little easier for us back then. And we didn’t have these phones, so people were more social. You know what I'm saying? You get into an argument, you slap the shit out of someone, you keep moving, and y’all friends the next day. Ain’t like that no more. People be cowards hiding behind these phones saying all kinda… getting you hyped up!

What is the difference between people on their phones talking shit and doing it face to face?

You know, at the end of the night, everybody would be dancing. “Child, we over that.” Know what I'm saying? You couldn’t be anonymous and just keep shit going; you had to confront the stuff right there—have it out at the bar, talk with your girlfriends. “Okay, bitch we had to fight this week, now we know where we stand, but we still coming to this club, we still gonna hang out, we ain’t gonna kill each other.” That's how we were back then.

What surprises you the most about this younger generation?

Nothing bothers me! They’re all pretty good girls. A lot of girls are getting careers. Everybody should stay in school, especially trans girls. Everybody should get some credentials. Everybody should get registered. If you don't want to go to school, find a trade. Either food, health, or clothing. You can always find a job—people need to eat, people get sick, and people need clothes.

I haven't turned a trick since 1980-something! I heard girls are doing it for five, ten dollars. Oh my goodness, we just used to have sugar daddies. That hasn’t happened in years. They used to love us. Millionaires used to come into the Baton a lot. A lot of the girls found their husbands at the Baton.

The Baton brought a lot of girls out of the closet, too. I wasn’t thinking about being a drag queen. I was thinking about being a girl! Is that weird? I knew I was a girl. [As a kid,] I was a tomboy, I liked climbing trees. I had barbie dolls, army men; because my sisters didn’t want the dolls and they’d give them to me. My mom would buy me army men to make me a boy, but I’d have the best of both worlds, I’d have the army men guarding my barbies, hello!

I’m glad my family accepted me. That's another thing. You know, my family did accept who I am, who I was, who I came to be.

One time I was sitting at a bar, it was Christmas. I asked this girl what she was doing and she said, “I can’t go see my family, I haven’t seen them in 10 years.” I was devastated. That had ruined my whole night thinking about that baby didn’t have nowhere to go. I invited her to my house, she didn’t come, but I invited her for Christmas. I can't imagine not being able to go home. But some people like that, you know, they have a situation where they can’t go home to their family. My heart goes out to them.

You are a mother figure to so many people.

Thanks to all those elders from the gay community. They embraced me. They took me in the right direction away from the street, away from crazy queens. I was fortunate to have good people in my life.

I did have a bout with the drug thing. I was 40 when I started dabbling in the drug thing. Isn’t that crazy? What happened is, I started dating a drug dealer. You know how they have rolls of money—singles? This guy would buy me anything I wanted. This one didn’t have rolls of singles, he had a roll of hundreds. What’s a girl supposed to do, when he was bringing me hundreds of dollars every day?

Back in the early 90s, when people were selling powder, I got wrapped up in that for a while. One day I walked out. My sister was working for the post office. We were in a building where we grew up as children, sitting in the window. I said: “Look at me, I need to just jump out this window. Spending money on all this bullshit. I wish I was normal.” I sent that out into the universe and three months later, it was gone. I never looked back.

I know why. One day I was getting high and snorted too much. I was on my way to work. I think it had to be 1992 and I got on the Red Line. I couldn’t catch my breath. I really could not. I laid in the middle of the Red Line train, on the ground and asked God for strength. By the time I got to the Baton, I caught my breath, went to work, and I think I got fired the next day. My boss saw what was happening to me; he wanted no part of it. He wanted me to go get some help, but he fired me, that was his way of telling me to go get some help. So I went on unemployment and went to my first AA meeting in 1993.

I'm worth it. That's what I figured out. I'm worth more than any drugs, any man, any person. I'm worth it. I love myself today. My mother told me before she passed, she said, “I think your community of girls are the strongest people on the planet because you have the courage to be who you are. No matter what nobody else says.” So if I can pass that on to other girls, then I think that's the best thing. We are more courageous than we think, because we have the audacity to live our lives how we feel we should.

I mean, it takes time. I go out every day and I don’t even think about it. I'm just me. I don’t think I'm dressed like a girl. I want to be cute, I just put something on to go outside. [My mother] said, “That’s courageous. Transgender people are one of the most courageous people on the planet.”

When you’re true to yourself, you not hurtin’ nobody. Doin' something to make yourself happy, that's genuinely valid.

You’re not out here trying to fool these boys—tell them the dirt! Keep it moving. They may say something smart. So what? You are trans, so what? Now what? And if you don't like it, then don't. Go about your business.

Boys will try to talk to you. But you can't trust these people now, you got to be truthful. Their agenda may not be your agenda.

I met this fine ass guy ten years ago. We danced at the bar all night. We went to the hotel. We had beautiful sex. After sex it was like, I was a dirty slut. He didn't want to look at me. He wanted to hurry up and get out. I mean, he just felt so bad. I sat, looking at myself, feeling bad for him. We had the best night. He was a freak; I was a freak. [But] you gonna wake up beating yourself up over being who you are. I feel so bad for him. I mean, he was literally going crazy trying to analyze what he just did—and I wasn’t his first time, trust me. I wasn’t his first. And I don't even really do that, but that night I was like, whatever. Because I’m a dirty bottom more so than a top. That’s just me. I had to be in a freaky mood to be like that. I lost my inhibitions with him. Like it's crazy, this motherfucker went crazy. He said “I gotta process what just happened.” In my mind, I thought, You’ve processed this more than once baby, because this wasn’t your first time!

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Did he deny it?

He just did not really want to be there the next day. He wasn’t secure with who he really was.

He got dressed and left. I’m saying all that because he wasn’t like that when we were dancing at the gay bar! We danced all night.

At a gay bar!

When he came to and got his orgasm, he turned into, “I’m a straight boy.” I was like, “Okay, girl. Get yourself together.” Lord have mercy on these straight boys.