Singer. Dancer. Actress. Sargeant. Bartender. Fundraiser. Activist. Icon.
Since the early 1970s, Diane Gregory has played many roles in Milwaukee – both onstage and offstage. After years of service to her nation, her employers and her community, she’s now celebrating her first year of service entirely to herself. Impacted by COVID-related business closings, Diane decided it was time to retire from the workforce.
For years, the Wisconsin LGBTQ History Project has been chronicling the authentic voices and life experiences of our community. We’re honored to share the voice of this unsung hero.
A star is born
Diane Gregory was born Sept. 3, 1957 on Milwaukee’s northwest side. Her father came to Milwaukee from Missouri for work, accepted a job at the Howard Avenue Water Works and stayed 40 years until his retirement. Her mother was a lifelong Milwaukeean from the South Side.
“I got the name Legs in high school,” explained Diane. “People used to call me ‘Gregs’ – short for Gregory. Then, they saw me tap dance one afternoon with a swing ensemble, and ‘Gregs’ became ‘Legs!' It’s been my name ever since.”
Diane started dancing when she was eight and never looked back. She is still in touch with her childhood dance teacher, now 86. She did all sorts of dance – tap, ballet, baton – and performed in school musicals. She was always fascinated with choreography and tried to work her dance skills in somehow.
Diane attended John Marshall High School. During her senior year, she and best friend Pat Carney were fascinated with Mr. Jerry Grillo, the dashing young choreographer for their high school musicals. "Pat had a crush on him,” remembered Diane, “and she knew where he hung out.” One night, they followed him down to The Factory, 158 N. Broadway. That night changed her life forever.
“I remember walking in, and feeling the music, and seeing the crowds, and just realizing this is where I belong,” said Diane. “The minute I walked in, I knew immediately. And we danced the entire time we were there! The whole night! Just danced until we were dripping with sweat and ready to collapse.
“From that day forward, I lived there every weekend. To this day, the smell of Aramis brings me back!”
Diane remembers seeing Paul Lynde and Milton Berle at The Factory, just mixing in with the usual customers, but it wouldn’t be the last time she saw celebrities out on the town.
From spectator to starlet
Over time, The Factory became as famous for its drag shows as it was for its dancefloor. The Loading Dock area, in the back of the building, became an impromptu stage many nights.
“There might have been drag shows at other places, but I only remember seeing them at The Factory,” said Diane. “Factory was so mixed: It wasn’t uncommon to see women there, whether they were femmes, fag hags, it didn’t matter. All kinds of people were there and everyone just fit in.”
One fateful night, Diane graduated from being part of the audience – to part of the cast!
“Tiger Rose was doing a show, and from the stage, she pointed at me and asked if I was a girl or a boy!” Diane remembered. “I was wearing red pants, a white t-shirt and a red headband. I looked like a little butch dyke. And she seriously didn’t know what I was. Later, she apologized for embarrassing me, but I really wasn’t embarrassed. And then she said to Pat and I, 'We’ve seen you and your friends dancing. Have you two ever thought about being in our shows?'
“They were really doing shows just for fun. They’d decide, ‘We’re doing this show,’ and we’d buy the album, pick our parts, rehearse our numbers and go live a few days later! They really put their heart and soul into these little shows: the music, the moves, the set, the costumes. They really went all out. Pat and I were so excited to be part of this team.”
Diane remembers her first show, in 1975, which featured Mel Powell, DeeDee Darnell, Mother Chris, Tiger Rose, Mama Rae, Riki Vegas and Jerry.
“We called ourselves the Entertainers Club. I mean, we had jackets and everything!”
The Entertainers Club performed extravagant productions at the Crystal Palace (1925 W. National Ave.), formerly the Knights of Pythias Castle Lodge, built by a German fraternal organization in 1921. The venue, now on the National Register of Historic Places, hosted punk and speed-metal shows later in the 1980s.
“These were some big hair, big costume numbers,” said Diane. “Mama Rae and Tiger Rose would show up with five wigs and a rack of dresses each. I had a little suitcase on my lap. Things sure have changed since then.
“For one number, they even put me in a damn dress. The song was ‘A Beautiful Girl,’ a bit of a Miss America medley, and we were all dressed to the hilt. At the end, the whole cast smiled with these big toothy grins – and we’d all blacked out one tooth. The audience roared! Our director was so mad, but he couldn’t say anything, because people loved it. We did this same show several times. We even performed at Snap-On Tools!”
Diane became close with Tiger Rose, also known as Ed Schicker.
“I didn’t know what queens were all about,” she said. “I had a lot to learn. He lived quite a secretive life, working as a man in flannel and jeans by day, dating a boyfriend who only knew him as Tiger Rose by night. They’d get high and go out on 20th and Brown Street to pick up guys. Just so wild to think about now.”
“One of the reigning queens was Mother Chris,” said Diane. “I actually lived in her house at Pleasant and Jackson streets for a few months, which was very unusual, because Mother Chris did NOT like girls at all. She was old, crotchety and cranky. I remember her sewing costumes and doing hair for Dawn Koreen.”
Some of Diane’s other acquaintances from The Factory era included pageant winners Mickey Chanel and Vicky Renae, among the first trans women to have gender affirmation surgery in Milwaukee. She remembers visiting Riki Vegas at his coffee shop on Water Street. She also remembers Mama Rae’s secret ingredient for the perfect bosom: bird seed!
Eventually, Mama Rae moved away, lost both her legs to diabetes and passed away. Tiger Rose died of a heart attack in March 1989. Survivors found a photo of Diane in her military uniform in his wallet.
“The funniest thing, though, was that after the military, I never saw some of these people again. I don’t know where they went or what happened to them. Somehow, in a city this small, we just drifted apart.”
United, we stand
Although Diane was more into dancing than dating, she did meet a girl at The Factory. She also remembered hanging out at the Leaded Shade (157 S. 1st St.) during this era. For the most part, though, she hung out in a mixed crowd.
“I didn’t have anything against the women,” she said. “I just felt more comfortable being around a mixture of people. Thanks to Tiger Rose, I saw the whole community as a whole. I wasn’t just exposed to gay women, but to gay everyone. That’s why I called myself a gay woman – because we were all gay, together.
“Women really didn’t want to mix as much as the men. I had a friend from high school who went straight to Leaded Shade and never looked back. For the rest of her life, she only hung out with those women. She never saw a social life past that.”
The women’s scene was still evolving in 1975, as the older, more rigid sexual expression of earlier generations was slowly fading away.
“When I first came out, I met older women that strapped their breasts down,” said Diane. “They were really committed to being butch. They had two choices: butch or femme, and it was one or the other. No exceptions. They didn’t have much use for me.
“It somewhat freaked me out because I’d never seen anything like that. It was not really a thing my generation did – nor did we feel we had to. The older women felt they had to do this.
“After I became a performer, I was always wearing fancy clothes. So, I think I was more butch when I was younger. But to be honest, I hung out with diverse people in diverse groups. Maybe that’s why I never felt pressured to declare anything. I knew what I liked, and I still do, but it was my business.
Diane's only other hangout was the River Queen.
“We had to go there Thursday nights when Sharon was the door person so we could get in," she recalled. "We were so young and so poor, and this beer bust was about all we could afford! I just remember this long, thin, narrow bar – and thinking it’s too small to be comfortable in here. It was like a hallway with a tiny dance floor at the end.”
Diane can’t remember ever being in a bar that was raided or shut down.
“The weirdest thing for me was going places that were in such bad neighborhoods and not being able to find the place, and wondering if there really was a bar," she said. "You never really knew what you’d walk into. It’s so hard for people to understand that now.”
Diane remembers her first pride event: the Chicago Pride Parade of 1975.
“I went down to Chicago with Debi Vance for the day,” said Diane. “It was like our very own Woodstock. We were all together in the park, singing ‘United We Stand, Divided We Fall,’ and I was just beaming. I may even have been crying. I knew, without a doubt, that this was my community, and these were my people. That’s what’s missing now. That togetherness. Those meaningful, memorable moments that make you tear up almost 50 years later!”
Diane joined the Air Force for the next four years. She was stationed at Langley Air Force Base in Virginia, Travis Air Force Base in California, and later, overseas in Germany.
“I was in Europe for nine months, but I was too young to really appreciate it all," she noted. "Paris, Amsterdam and so many other places – and I didn’t get what I was even seeing.”
Diane remained in the closet during her military service.
“I didn’t really join the Air Force to find a girlfriend,” she said. “I knew that would just get me in trouble.”
During basic training at Lackland Air Force Base in Texas, she won a dance trophy – dancing with a guy in a pencil skirt.
“I looked like a guy for a long time, so I definitely was self-conscious of that,” said Diane. "People were always thinking I was a guy. I never went out in the straight world. I had this big banner across my face saying I’m gay. Before I went into the service, I didn’t care. But during the service? Oh hell no.”
Out and proud
Ready to be herself again, Diane returned to Milwaukee in 1979.
“On my first day home from Europe, I went over to Mitchell Field and my friends were playing ball,” she said. “I remember going to National Liquor Bar and picking up German wine. That’s just the kind of community we were back then. You’d show up somewhere, and within a few minutes, your whole circle of friends would all be there, too. We had a real society.”
By 1979, Milwaukee nightlife had changed a lot. The River Queen was gone, the Leaded Shade was gone, The Factory was starting to fall out of favor and more new bars were opening every month.
Beer Garden had become the popular women’s bar, and Diane found herself spending a lot of time there. She played softball on the Beer Garden team, bartended Sunday afternoons and even performed in shows at the bar. She has warm memories of owners Sally Szewcyzk and Roger Emerson, later the owner of the Empire Lounge (716 N. Plankinton Ave.) and Rainbow Grille, 814 S. 2nd St.
Diane remembers what a shock it was when drag queens would show up at the Beer Garden.
“I loved bringing the queens down there, because some of these women had never seen a drag queen in their life," she said. "It was so fun to see their reactions!”
“There was no other bar like the Beer Garden,” Diane added. “When Sally and Roger retired, they sold to some women who tried to keep it going. It just didn’t work. And the next thing you know, the entire block was gone. And today, it’s just this empty piece of grass!”
The original Factory closed in 1982. By that time, Diane had moved over the M&M Club (124 N. Water St.) which became her new home bar. Although The Factory would later reopen at two other locations, Diane didn’t follow.
“Poor Chuck kept trying to make the magic happen again – but there just wasn’t anything as magical as the original Factory.”
In addition to Beer Garden and M&M Club, Diane visited the women’s bars of the era. She missed out on the Sugar Shack (135 E. National) until it was D.K.’s in the 1980s. She remembers dancing at the Lost & Found (618 N. 27th St.), then the hottest women’s disco in town, playing on their softball team and later doing shows at the club. She also enjoyed Fannies (200 E. Washington) where she met longtime friend Mary Connell and performed in a number of Fannies Fests and fundraisers.
“Nowadays, women will tell me how they thought I was ‘unattainable’ back then,” said Diane. “I have to laugh! I would go out alone and hope someone would talk to me. It’s so funny to think how I was perceived. If they only knew!”
The Great Disappearing
Diane renewed her interest in song and dance.
“I was part of the original Fest City Singers, way back in 1985," she said. "We traveled all over the region, performing at galas and theaters, and meeting other singers and artists. I always wanted to do really fun stuff – Gershwin, Broadway, Old Hollywood – and I really loved choreography. Our director was wonderful, but some of the members were very, very serious. This led to a split between Fest City Singers and what became the Cream City Chorus.”
Diane remembers the Fest City Singers as a light-hearted, fun-loving bunch – until the specter of AIDS began to loom over the community.
“I can still remember the first time I met someone with AIDS,” said Diane. “My partner and I saw Bobby Uyvari at Club 219. We ran over to him and hugged him, like we always did, and he was so tense and so stiff. He looked shocked. We asked, is something wrong? And he said, 'Nobody hugs me after I tell them I have AIDS.' Can you believe that? Of course, we didn’t really know what was happening, or what was about to happen to us all.
“The chorus was often called to perform at funerals,” she added, “and it would always be so shocking to find out whose. You would hear someone was sick one week, and the next week, you were going to their funeral.
“I still remember the day we sang at Bobby Uyvari’s funeral at Villa Terrace. He was the first person I knew with AIDS, and he had made such a difference in all of our lives. As we performed ‘You’ll Never Walk Alone,’ the doors of Villa Terrace opened and closed with a sudden wind. I’ve never seen anything like it.
“That was the day we knew what AIDS was all about. It was the beginning of the end of all these wonderful people, of all those happy memories, of an entire way of life. And it was just beginning.
“I noticed it most at M&M Club after the Factory closed. You’d stop and think about all the people who had passed away. You’d stop and think about how you might be next. You’d hear people expressing regret, even remorse, about the way they’d lived their lives. What did we all do? Was this the big reckoning? When we were in our 20s, we thought we’d live forever, and now people were dead before 30.
“People were scared. There was SO much fear, but somehow, there was even more sorrow. We were such a close community. We only had each other. And we were losing people we loved every, single, day.
“Don’t get me wrong, we all experience loss in our lives. But AIDS was loss on such a massive scale: It was relentless, it was intense, it was constant heartbreak. Humans just aren’t built to emotionally or physically handle that much loss. If you were there, you know.”
Baby, remember my name
The show went on, because it had to. In many ways, entertainment kept a shattered community connected.
Miss Gay Wisconsin started at The Factory in 1974 and moved to the Centre Stage Theater at the Antlers Hotel (616 N. 2nd St.) in 1975. By the late 1980s, drag pageants had become wildly successful, high society affairs. Before government agencies and national organizations were supporting the cause, the local community hosted homegrown AIDS fundraisers.
“People would get dressed up like they were on 'Dynasty,'” Diane remembered. “Bars and groups would buy tables and offer tickets to people who couldn’t afford them. You’d get a room for the night. And once the show started, the night would kind of just fly off the tracks!
“There were so many contestants. We gave out awards for community contributions. I only wish I had saved all my photos!”
Diane distinctly remembers the first year the Marc Plaza (now Milwaukee Hilton) hosted the Miss Gay Wisconsin pageant.
“The waiters were all wearing rubber gloves because they thought they would catch AIDS,” said Diane. “I’m not even kidding. They thought they’d catch AIDS from touching our dishes and glasses. In response, the hotel put out this bogus statement and made themselves look even worse! It was outrageous.”
Diane remembers when there were many women’s social groups to choose from, as well as benefits, tournaments and fundraisers that brought out women who didn’t usually go to bars. She remembers community leaders like Lois Ratzow and Cindy Schumann always organizing women, as well as sports events like Holiday Invitational Tournament (HIT) and the Saturday Softball Beer League (SSBL). She remembers landmark events like Ms. Gay Wisconsin, founded by Debi Vance and Cindy Olsheske at Club 219. She remembers the women’s bars – Lost & Found, Hot Legs, Dish – that came and went over the years.
“It was surprising how much AIDS brought women together,” said Diane. “The benefit shows. The fundraisers. Possum Queen!”
Over time, Diane has become famous for specific musical numbers.
“I started doing Irene Cara’s ‘Fame’ at the M&M Club,” said Diane. “When I hear that number, it just takes me back, and I remember how it felt to perform it time and time again. Every time I did a show, they’d just put it on, even if I’d already done my real number! So ‘Fame’ just became my number. And that’s alright, because I really like what the song says.”
Some of Diane’s other favorite numbers include Pat Benatar's “Hit Me with Your Best Shot” and Carole King's “I Feel the Earth Move.”
"That was the first song I ever did solo at The Factory,” said Diane. “I was mighty hot in my green fringe outfit!”
The beat goes on
Since the Armed Forces, Diane has worked in a variety of financial services jobs, including Fleet Mortgage, Time Insurance and Northwestern Mutual Life, as well as an array of hospitality and service industry jobs. Most recently, she was part of the opening team at Saint Kate Hotel. After retiring in 2020, she’s been spending her newfound free time socializing with friends, volunteering at Hunger Task Force and performing in the occasional show.
She eagerly awaits the return of the Old-Timers Party, a regional women’s reunion that occurred every January for 40-plus years before being cancelled by COVID.
She’s also revisiting her passion for photography.
“I was always inspired by Life and National Geographic,” said Diane, “so I took a photography class at Alverno years ago. I’m ready to go deeper into this now that I have the time.”
“To the next generation, I say this,” said Diane. “Be careful what you wish for.
“Lots of women my age complain, ‘You can go anywhere now with your lovers and friends, but it doesn’t feel like a community anymore. The gay bars are all closing. The gay groups are disappearing. The gay traditions like HIT are ending. These board members can’t find people to replace them, after doing this for 20-30 years themselves. No young people want to step up to lead gay organizations anymore.
“We are the ones who made that happen by living our lives. We have these freedoms because we lived our lives. This is what we wanted, wasn’t it? To be accepted? To feel safe in public? To be part of the world? To go anywhere we wanted to go? To bring 50,000 gays together on the Summerfest grounds?
“As thankful as I am for the changes we’ve achieved, I am thankful I was around back then. I had a family back then. I was fortunate to be part of that family. It was like a secret club. It was like our private playground. I feel like we’re more connected than ever, through technology, but we can’t find each other anymore. It’s become so impersonal.
“At the same time, I’m worried about people segregating themselves more and more,” Diane added. “At one time, the rainbow was meant to represent the unity of everyone coming together. I feel like we’re heading towards this great division with everyone moving to separate corners. I wish we could stop the anger and stop the separation, because it’s going to tear the community apart.
“If I were just coming out today, I’d come out much earlier. It’s so awesome to see confident young people knowing exactly who they are. I knew who I was, but at the time, I snuffed it out. I wouldn’t have to do that now. I might even have dyed my hair purple! That sense of freedom, being able to do whatever you want without rules or repercussions, is just intoxicating.
“I have had a wonderful life in this community. I’ve been lucky. I’ve been loved. And, today, I feel like I am free to be gayer than ever.”
Want to learn more? Explore over 100 years of local LGBTQ heritage at the Wisconsin LGBTQ History Project website. Our mission is to reconnect Wisconsin with its hidden LGBTQ history and heritage.