Meet the First Miss Pittsburgh

How does a 24-year-old good looking guy named Mike who lives in New Kensington, made Sergeant in the Air Force, and has an 8x10 drag photo on his mother’s mantle, get to be Miss Pittsburgh?

Photos by Dan Murano

On March 20 [1977], a relatively unknown talent graced the stage of the Allegheny Starlite Ballroom and competed with 11 other ”drag” entertainers for the title of “Miss Pittsburgh,” a first for this city. The audience did the judging by paper ballot, and a “Dawn Montgomery,” known when not in drag by his real name, Mike, emerged as the Steel City’s original “Miss Pittsburgh.”

This article originally appeared in the July/August 1977 issue of Gay Life Pittsburgh and is republished here for the first time in over 43 years in it’s entirety as originally published. Some language is dated. Help us preserve Pittsburgh’s LGBTQ history, like this article, by contributing to our GoFundMe.

Hearing that “she” was very opinionated, guest writer Joseph Bowden set out to interview Dawn, and what follows is a transcription of that interview.

Mike, or Dawn if you prefer, has lived in several cities here and abroad that are more cosmopolitan than Pittsburgh and offers some comparisons. Although presently working at the Cinema Follies Club downtown, 24-year-old Dawn informed Gay Life that among entertainment skills there exists a bypassed career as a drama teacher (“I just can’t find work!”) as well as that of a hairdresser and makeup artist. So now, meet Dawn Montgomery, “Miss Pittsburgh“. . .

GAY LIFE: How did you choose your name?

DAWN MONTGOMERY: When first starting to go in drag in Washington, D.C., I went out as Miss Diane Cannon and then someone said, “Hey, go to this function in drag and adopt your own identity, so Dawn Montgomery came out. The event was the Academy Awards, or the Oscars, an event sponsored by drags for drags every year. We have our own organizers there, and rent a fabulous ballroom for the Awards.

GAYLIFE: How long have you been going out and entering drag competitions like that?

DAWN MONTGOMERY: This Halloween, it will be four years.

GAY LIFE: Will you be using your title, Miss Pittsburgh,” when entering competitions in other parts of the country? Is “Miss Pittsburgh” a steppingstone to some sort of national pageant?

DAWN MONTGOMERY: I intend to go back to the Oscars, in DC, as a former DC titleholder but most recently as “Miss Pittsburgh,” and say, “Hey, look at me!”

GAY LIFE: Do you consider yourself a professional?

DAWN MONTGOMERY: Do I? I don’t even know how to deal with that.

GAY LIFE: I suppose part of it has to be monetary. An amateur might only get $50 per night to do a drag show at a bar, whereas a professional commands a higher salary.

DAWN MONTGOMERY: I won’t work for $50 a night.

By the time the lashes are on, I am Dawn Montgomery

Dawn Montgomery, Miss Pittsburgh 1977

GAY LIFE: What is your going rate?

DAWN MONTGOMERY: In Pittsburgh, I’ve worked at the Allegheny for door proceeds. In D.C., I usually start at $250. It depends on the place, what kind of show they want, costumes, and how the management is to deal with. If it’s a benefit, I’ll work for the tips sometimes depending on the cause.

GAY LIFE: What do you do in your shows? Mime? Comedy? Sing Live?

DAWN MONTGOMERY: I do a lot of mime and “sine.” If I could handle the voice, I’d love to go live and sing with some backup. But my voice just doesn’t have the range—I’d sound like Lauren Bacall with laryngitis. But mime is okay. I really respect drags who can mix costume, makeup, movement and voice.

GAY LIFE: Don’t you think that simply “mouthing” to records is sort of passe these days—that gay audiences expect more?

DAWN MONTGOMERY: Not if it is well rehearsed, the costumes are fabulous, and the choreography is there.

GAY LIFE: What do you actually have to do to transform from Mike into Dawn?

DAWN MONTGOMERY: (Sigh) It’s not that easy. I do it differently than the drags I’ve met in Pittsburgh. As far as I know, most of the queens here use regular makeup. I use theatrical makeup, starting with a clown white base. Before that I put astringent on my face and then tape my brows. Most pluck or shave their eyebrows, but to me part of the challenge is to not look like a woman when I’m out of drag. When you pluck your brows guess what happens? So I don’t do it. When you’re out of drag you don’t—or I don’t—get up and start doing a number with a moustache, 5:00 shadow, and short hair. And when I’m in drag I don’t go around taking swings at people. It’s like two different personalities. Anyway, put on liquid blush, then Muron everywhere, eyeshadow, liner, lashes. When I’m doing a show I try to keep everything coordinated so that my eyes will match the outfit changes.

GAY LIFE: How many changes, usually?

DAWN MONTGOMERY: The Miss Pittsburgh Pageant required three changes.

GAY LIFE: Do you do all of this yourself?

DAWN MONTGOMERY: Oh yes. And then right before the show there’s a final check—powdering down, outlining, the lips, the nails, the bust, hair—everything. Then I don the jewelry and slip into whatever I’m opening with.

I used to run into the barracks after being out all night, rip my hair off, and nobody who wasn’t supposed to know ever did.

Dawn Montgomery, Miss Pittsburgh 1977

GAY LIFE: This all sounds very expensive.

DAWN MONTGOMERY: Since last December I know I’ve spent over $800 on drag paraphernalia.

GAY LIFE: Do you have difficulty adjusting your personality from Mike to Dawn?

DAWN MONTGOMERY: It sort of happens when you’re doing the makeup. You can see yourself changing in the mirror, and it goes to your head. I take a cigarette and notice that I’m puffing it gracefully instead of inhaling and exhaling like a man. By the time the lashes are on, I am Dawn Montgomery.

GAY LIFE: You don’t feel ’drag queen” is demeaning?

DAWN MONTGOMERY: It depends on who’s talking. If a straight guy comes up and yells, ’Drag Queen!,” I have no time for him. But my mother can call me a drag queen—she tells people, ’’This is my drag daughter.” She thinks it’s kicky, and that’s okay. To me, an impressionist is someone who does it live—not to records. A transvestite isn’t a performer at all, but a male who gets off being in women’s clothing. A transsexual wants to have a sex-change operation, all the way. Oh please, just call me a drag queen.

GAY LIFE: What about your social life—is it mostly in drag or not?

DAWN MONTGOMERY: Out. I’ve gone out socially in drag only three times in Pittsburgh—to the Tilden and Allegheny. It’s just too much work, and it doesn’t conform to my sexual preferences. Too many gays put down drag queens, and I don’t need someone who wants to go to bed with me because he thinks I’m a woman, or digs guys in women’s clothes. I’m a man and want to be appreciated by someone who thinks of me as a man.

GAY LIFE: Those gays who put down drag, or you in particular—how do you handle them? Surely you’ve had confrontations.

DAWN MONTGOMERY: It depends. If they’re real asses I’ll either ignore them or get rowdy. If I think they are capable of carrying on an intelligent conversation I’II try to talk to them. I’ll say, ‘Hey, remember me?” the next time I see them out of drag and explain that going in drag is just a way of expressing one’s self. It’s a legitimate form of entertainment and almost unique to gay life. Right now I’m still on an ego trip. No one else in Pittsburgh can say that they came home to a city where hardly anyone knew them, and as a dark horse contender, won a fair contest that was judged by audience voting. The only people who knew me at the Allegheny were John the manager, my mother, father, sister, and some of the other contestants. Others brought contingents to vote for them, but I won. What can I say? Thank you, Pittsburgh… .

GAY LIFE: Your family was in the audience. I remember seeing your sister, as soon as the winner was announced, stand up and scream with pride. “That’s my brother! ” The relationship with your family must be very good if they’d come to an event at an all-gay club to see you in drag.

DAWN MONTGOMERY: It is—I’m very lucky. It’s only been the last year or so that we’ve gotten along well. I think it s because they can now deal with me honestly for who I really am. I came out to them as a gay and as a drag queen. I went into the service when I was 17 and it wasn’t until I came back, about a year ago, that we could really talk. Coming out helped a lot.

My father came up on stage and that meant a lot. A year before we were hardly speaking.

Dawn Montgomery, Miss Pittsburgh 1977

GAY LIFE: You were in the service?

DAWN MONTGOMERY: The Air Force. I went in drag while I was in. I used to run into the barracks after being out all night, rip my hair off, and nobody who wasn’t supposed to know ever did.

GAY LIFE: How could you get away with that?

DAWN MONTGOMERY: That’s when I really got started in drag. I was stationed in Maryland near D.C. and just getting into the Academies. I lived in the barracks so I’d just have to rush in and become Mike again.

GAY LIFE: But how could you just walk into the barracks in drag?

DAWN MONTGOMERY: Through the side door. I had my room on the first floor, so nobody ever caught me. Dormitories were out—we had private rooms. There were four to a room, and then when I made sergeant—yes I did—I got my own room. For a long time I even used my own hair in a Liza Minelli cut. Off with the lashes, the makeup, and into the shower. I guess I was a brazen bitch. There were other gays on base and they all knew.

GAY LIFE: I don’t imagine any of them went in drag, though.

DAWN MONTGOMERY: I don’t think so. I was given the unofficial title among the gays on base of “Miss Fort Mead.” There were about ten of us, and we would congregate sometimes and exchange stories about the officers we’d seen at the bars the previous weekend. Most of us had good jobs and we worked for them. I was in security.

GAY LIFE: Back to your family—was the Miss Pittsburgh Pageant the first function they’d attended to see you perform?

DAWN MONTGOMERY: They’ve seen me in drag before at home, practicing. But that was the first time they’d come to a gay club. My “Miss Show Business” (DC) trophy and an 8 x 10 glossy of me in drag sits on my mother’s mantle.

Pittsburgh is one of the nicest cities I’ve lived

Dawn Montgomery, Miss Pittsburgh 1977

GAY LIFE: What did they say to you immediately after you won?

DAWN MONTGOMERY: It was sort of rushed. They were going home and I was going barhopping. My father came up on stage and that meant a lot. A year before we were hardly speaking. We despised each other, I think. Before I went into the Air Force, he used to call me a sissy.

GAY LIFE: You mean he called you a sissy but didn’t know you had homosexual tendencies?

DAWN MONTGOMERY: At 17, I didn’t even know. I didn’t come out to myself until I was 19 or 20. Then it all happened so fast.

GAY LIFE: And now that he knows you’re gay, it’s alright?

DAWN MONTGOMERY: Yes. We were talking a few nights ago and I told him, “Guess what? Gay Life is going to interview me and maybe even put me on the cover. How do you feel about 5,000 copies of that all over Pittsburgh?” He encouraged me to do it.

GAY LIFE: How do you think drag queens can help advance the cause of gay acceptance?

DAWN MONTGOMERY: In a way it’s easier than it is for gays who are not into drag. There’s a shock value to it. We’re less inhibited. If a straight person finds out I do drag shows, or sees me in drag, he can’t get used to it. If he’ll listen, I can get him to understand the drag part of it and then the gay thing is easier to deal with. He’s already been conditioned. There’s less shock to it. Many people don’t expect a drag queen to talk intelligently, so they’re taken back when one does.

GAY LIFE: Would such a person. .. .

DAWN MONTGOMERY: Wait a minute. I’m not talking about make-believe people. I’ve really had conversations like this.

GAY LIFE: Do these people come away with the idea that all gay men go in drag?

DAWN MONTGOMERY: No way. I sit down and explain it all. You can’t really explain gay life in 25 words or less but you can paint a picture with everything in proper perspective. Drags are a part of gay life, and part of society. Pittsburgh is kind of slow on drag, and it bugs me. Not many people seem to be into it. I guess I was spoiled by D.C.— everything is so much more open there. Other than that, Pittsburgh is one of the nicest cities I’ve lived in, and I was born near here and my family’s here. I intend to stay. I’ve lived in Rome and other glamourous cities, but I’ve met more people here who actually care than anywhere else.

GAY LIFE: Do you really buy into this “someplace special” propaganda?

DAWN MONTGOMERY: Yes, as far as the people are concerned. As far as drag goes, Pittsburgh has a potential but drag here isn’t very advanced.

GAY LIFE: Turning the tables, how can other gays advance your cause?

DAWN MONTGOMERY: Simple. Just be accepting. Live and let live. We re all fighting for the same things, aren’t we?

The Q Archives and articles like this are made possible by the kind contribution of Tony Molnar-Strejcek, the publisher of Pittsburgh’s Out and by contributions by readers like you.

The Q Archives and articles like this are republished here by the kind contribution of Tony Molnar-Strejcek, the publisher of Pittsburgh’s Out. Maintaining the cultural history of Pittsburgh's LGBTQ Community is made possible by contributions by readers like you.