There is a long history of performers using clothing, makeup and hairstyles to express gender. These were among the first to make waves.
Although the term “drag queen” only came into wide acceptance around the mid-20th century, there is a long history of people using clothing, makeup and hairstyling to express gender and entertain others. More specifically, Joe E. Jeffreys, a drag historian, video artist and professor at New York University and The New School, describes drag as “the theatrical exaggeration of gender.”
From the vaudeville circuit to reality TV, here are nine drag performers who made history.
1. William Dorsey Swann
The story of William Dorsey Swann—a formerly enslaved Black person, first-known self-described drag queen and one of the earliest-known American LGBTQ activists—was lost to history until journalist and historian Channing Gerard Joseph came across an article about him while conducting archival research in 2005. Since then, Joseph’s findings have reshaped the narrative of queer history in the United States.
Born on a Hancock, Maryland plantation around 1860, Swann later moved to Washington, D.C., where, in the 1880s, he became the leader of a queer resistance group consisting primarily of other formerly enslaved Black men. At a time before formal gay rights organizations existed, the group held drag balls in Swann’s northwest Washington, D.C. home, half a mile from the White House.
Presiding over these clandestine gatherings, Swann dubbed himself the “queen of drag,” which Joseph says makes him the first-known person to describe themself as what we’d refer to as a “drag queen” today.
“When we think about drag queens—especially female impersonators in the 19th century—we think about performers, rather than about the way that drag exists in and functions to create community,” says Dr. Lady J, a drag historian and performer. “Swann introducing the term ‘drag queen’ as an identity term and as a community leader title in and of itself is really significant.”
According to Joseph’s research, Swann was arrested numerous times during police raids of his secret drag balls in the late 1880s, as well as in 1896, on a false charge of operating a brothel. When convicted and sentenced to 10 months in jail for the latter, Swann applied for a pardon from President Grover Cleveland. His pardon was denied.
2. Julian Eltinge
Julian Eltinge wasn’t just the most influential female impersonator of the early-20th century: he was also one of the era’s most popular performers. Born William Dalton in Massachusetts in 1881, Eltinge began dressing up in women’s clothing as a child, performing in saloon drag acts in his early teens, and was taking on women’s roles in Shakespearean plays by age 18.
In 1904, he was cast in a Broadway musical about a man who disguises himself as a woman, earning him both critical acclaim, and a headlining spot on the vaudeville circuit and European tours. One of his stops was at Windsor Castle, where King Edward VII invited Eltinge to give a command performance.
But unlike Swann, Eltinge never referred to himself as a “drag queen.” According to Jeffreys, in the early 20th century, professionals like Eltinge preferred—and often demanded—to be referred to as “female impersonators,” or variations like “femme mimic” or “female illusionist.”
Eltinge also participated in staged boxing matches and boxing photos. This may have made him more acceptable to mainstream audiences, who attended his stage performances, and later, his films. Eltinge held such wide appeal that he appeared in a celebrity-filled 1918 promotional video for the “Liberty Loans” campaign during World War I. At one point, he was paid more per picture than Charlie Chaplin.
Eltinge also capitalized on his ability to transform himself from a stout, middle-aged man into a glamorous woman, developing his own line of makeup and skincare products, and a magazine full of advertisements for them. “He understood how marketing worked in a newly emergent women’s middle-class audience,” Dr. Lady J says.
While he may no longer be a household name, by touring the country “building large audiences’ taste for the art form,” Jeffreys says that Eltinge helped establish drag as a potential career path in America.
3. Crystal LaBeija
When Crystal LaBeija walked offstage as Miss Manhattan after placing fourth in the 1967 Miss All-America Camp Beauty Pageant, what began as a protest became the foundation of the house system in ballroom culture. “This was the moment she realized race played a factor in the standard of beauty,” according to the House of LaBeija’s website. Despite being a pageant titleholder and beauty queen, “all that the judges saw was that she was Black.”
Drag balls had been taking place in New York City for at least a century, but up until that point, they “were generally an individual sport, where a person might win best gown or best hat” Jeffreys explains. “Crystal changed that, so that people competed as part of a house—like a baseball or basketball team—collectively competing to win the prizes for various categories, for the honor of your group.”
After the 1967 competition—which was captured on film and featured in Frank Simon’s 1968 documentary The Queen—LaBeija’s friend and fellow Harlem drag queen, Lottie, convinced her to organize her own pageant. This pageant was created by and for people of color, and was promoted through a group called the House of LaBeija.
LaBeija’s role included serving as a mother figure to unhoused LGBTQ+ youth and a mentor to other members of the house, cementing the now-familiar concept of the “chosen family.”
Nearly 60 years later, the house system is still going strong. “It has taken over the world,” Jeffreys says. “Houses and ball structures have brought about dance movements and fashion trends—it’s incredibly fertile, productive ground.”
Harlem drag balls thrived during the post‑Civil War era, creating a space where trans and queer people of color later broke out to develop House Ballroom.
Read more about How 19th‑Century Drag Balls Evolved into House Balls, Birthplace of Voguing
4. Darcelle XV
In 2016, Guinness World Records named Darcelle XV (pronounced “Fifteen”), then aged 85 years 273 days, the “oldest [active] drag queen in the world.” Born Walter W. Cole in 1930, the Portland, Oregon native first donned a dress at age 37 and adopted the stage name and alter ego “Darcelle” in 1969.
Two years prior, Cole purchased a dive bar that would become the Darcelle XV Showplace, a drag cabaret in his hometown that was listed in the National Register of Historic Places in 2020. Cole continued performing as Darcelle until his death in 2023 at the age of 92. The same year, the city named a downtown plaza in his honor.
5. José Sarria
After serving in the U.S. Army during World War II, José Julio Sarria was honorably discharged in 1947, and returned to his native San Francisco. There, he found work as a “hostess” and occasional singer at the Black Cat Cafe: a “bohemian haven” known for its artist, activist and LGBTQ+ patrons. By the early 1950s, Sarria’s performances were more frequent and more popular—especially his female impersonations and opera parodies.
Known affectionately as “Mama José,” Sarria also used his time onstage to advocate for gay rights in front of diverse audiences throughout the city—including the time he was invited to perform at the American Legion in full drag. But that all changed in 1955, when San Francisco’s newly elected mayor began coordinating with police and the military in an attempt to rid the city of its growing LGBTQ+ community and social scene: starting with shutting down gay bars and other gathering spots
Fed up with being treated like a second-class citizen, in 1961, Sarria co-founded the League for Civic Education: an organization that promoted gay civil rights and provided financial assistance to LGBTQ individuals who were arrested, and/or victims of discrimination. The same year, he ran for one of five seats on San Francisco’s Board of Supervisors, the legislative body for the city and county. Though he wasn’t elected, Sarria’s candidacy opened doors for other openly gay politicians like Harvey Milk, who won a seat on the same board 16 years later.
“He’s frequently credited as the first openly gay person to have ever run for public office in the United States,” Jeffreys says.
In 1965, Sarria helped found the Society for Individual Rights—another gay advocacy and community-building group—and established what would become the Imperial Court System: a network of nonprofit charities throughout North America, which is now one of the oldest and largest LGBTQ+ organizations in the world.
6. Divine
Born in Baltimore in 1945, Divine was a character actor, singer, champion of LGBTQ+ rights and the drag queen alter ego of Harris Glenn Milstead. After meeting filmmaker, writer, actor and artist John Waters in the mid-1960s, Divine went on to collaborate with him until her death in 1988—appearing in nine of his movies.
From the beginning, Divine’s drag was different. “There is before Divine, and there is after Divine,” Dr. Lady J explains. “Everyone before Divine was trying to look like a human woman. And then Divine comes along as the ‘Godzilla of Drag Queens,’ as John Waters called her. She was really the first person to make drag about being big and scary and threatening—something that many queens in the alt scene thrive on today.”
According to Jeffreys, Divine brought an edge to drag that had not previously been as visible. “Through the John Waters films, Divine had exposure and showed people that drag is not always polished glam—it can be punky, hardcore, edgy, and still just as fabulous, if not more so,” he notes. She also had a career as a disco star, Jeffreys says, and was particularly popular and successful in Europe.
While many Waters’ early films were experimental, he and Divine broke into mainstream popular culture with the 1988 movie Hairspray, where Divine played Edna Turnblad—the mother of Rikki Lake’s character, Tracy.
“She’s not this big, scary Divine character that she is in all her other movies: she becomes relatable, motherly,” Dr. Lady J says. “That breakthrough helped her achieve what she’d always wanted: to be a character actor who could do male roles and female roles.”
7. Joan Jett Blakk
In 1992, Joan Jett Blakk became the first drag queen to run for president of the United States. Though she entered the race on the Queer Nation Party ticket, Blakk made a memorable appearance on the floor of the 1992 Democratic National Convention in New York City, delivering her presidential platform in a red, white and blue American-flag-patterned minidress.
“If a bad actor could be elected president, why not a good drag queen?,” Blakk often quipped during her candidacy.
Prior to her presidential candidacies, Blakk ran for mayor of Chicago in 1990 as a way to bring more visibility to the ongoing AIDS crisis. Her final political run was in 1998, when she ran for mayor of San Francisco. She ran for president again in 1996—this time on the Blakk Pantsuit Party ticket.
8. Lady Bunny
Known for her work as a comedian, drag queen, actor, recording artist and DJ, Lady Bunny has been entertaining audiences since the early 1980s. She began her career go-go dancing in Atlanta, then relocated to New York City in 1984, where she appeared at the Pyramid Club: “one of the most important clubs ever for drag,” Dr. Lady J says.
The following year Lady Bunny organized the inaugural Wigstock Festival in the East Village’s Tompkins Square Park, featuring a wide variety of drag performers. The event grew—and became more mainstream—each year, consistently “attract[ing] large, diverse audiences” into the 1990s and 2000s, and serving as “a guiding star to RuPaul’s Drag Race as mass media,” Jeffreys says.
9. RuPaul
Although RuPaul began her career as part of Atlanta’s underground new wave and drag scene in the early 1980s, she’s best known for the carefully crafted, polished image she created in New York a decade later, around the 1992 release of her hit single “Supermodel (You Better Work),” Dr. Lady J writes in her doctoral dissertation, “From the Love Ball to RuPaul: The Mainstreaming of Drag in the 1990s.”
Prior to that, RuPaul’s drag persona “was based off of Black trans sex workers in the Meatpacking District,” Dr. Lady J explains. “Her character then shifts to this high-end ‘Glamazon’ figure, which becomes the thing that she actually can sell and promote.” The strategy worked, earning RuPaul a record deal, and a 1993 guest spot on the Arsenio Hall Show.
“There had never been a Black drag performer interviewed on late night before that, so for RuPaul to get that level of exposure and for it to be respectful and positive was wild,” Dr. Lady J says. By the mid-1990s, RuPaul had a MAC Cosmetics campaign, a talk/variety show on VH1 and small roles in films like The Brady Bunch Movie and To Wong Foo, Thanks for Everything! Julie Newmar.
In 2009, the first season of RuPaul’s Drag Race, a reality competition television series, aired on Logo TV, and has since given way to countless spinoffs and international editions. Though the show hasn’t been without controversy—particularly RuPaul’s initial refusal to allow transgender drag performers to compete on the show—it has thrust drag further into the mainstream than ever before.
“For me, it’s night and day,” says Dr. Lady J. “There’s before Drag Race, and there’s after, and there’s no going back to the way it was before. For good and for ill, Drag Race changed the landscape of drag like nothing else ever could have.”