Actors who portrayed women onstage have always been popular and likely go back to the beginning of recorded history. In Milwaukee, the first instance of a female impersonator on stage was 1884, and judging by the reviews, stole the show. This was a time when the art of female impersonation emerged from circus freak shows or dime museums and into mainstream theaters.
In the next decade, Milwaukee stage managers booked impersonators on a semi-regular basis. The Crystal, Star and People’s burlesque theaters appealed to working class audiences because admission was only a dime. Traveling productions that played these stages had at least one impersonator that brought down the house with jokes and songs in German, Irish and African American dialects.
The most expensive ticket in the city was a dollar at the Academy of Music theater or the Grand Opera House. These theaters presented shows for well-to-do audiences who arrived in top hats and expensive jewelry. “The Only Leon” appeared in June 1884, noting what is considered the first drag performance in Milwaukee's history. The term “drag” appeared in print around 1870, referring predominantly to theatrical female impersonators. Some associated drag with the long crinoline skirts that would drag across the stage. Another opinion held that drag may have been an acronym for “Dressed Resembling a Girl.” Whatever its origins, the term stuck.
Large Wardrobe
Leon began performing in minstrel (vaudeville) shows in 1858. Only 14 at the time, he quickly rose to fame by specializing in portraying prima donnas in elaborate costumes. Leon's 300 dresses were a key piece of his act, and some cost as much as $400. He called himself “Leon” or “The Only Leon" to distance himself from imitators in other shows.
Although impersonators were accepted on stage, a man wearing woman’s clothing in public might be mocked or even assaulted. The police typically arrested these men on the assumption they were street walkers. In 1899 police detained an unusual looking woman outside the Alhambra theater. At the police station it became obvious that he was a man masquerading in women’s clothes. The person’s real name was Harry Hynes, a female impersonator who performed at the inexpensive vaudeville houses. When arrested, he had been lingering outside the Alhambra to ask the manager for a job.
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The vaudeville circuit also brought the country’s top impersonators to town. Julian Eltinge, already famous for his theatrical female impersonations, cultivated a masculine persona off stage. He smoked cigars, peppered his conversations with vulgarities, and started bar fights. staged huge productions at the Davidson and Alhambra theaters after the turn of the century. He extended his fame even further after appearing in silent pictures.
Drag Balls
In the 1920s, Jazz Age women called “flappers” purposely reduced feminine curves and the size of their breasts. The tradition of masquerade balls, sometimes called “drag balls,” had begun in larger cities after the Civil War. At the height of Prohibition, the balls were attracting people of various races and social classes—gay, lesbian, bisexual, transgender and straight—alike.
Billed as the “Million Dollar Drag Queen,” Adrian Ames dazzled audiences in the late 1940s with a sapphire mink stole and a $10,000 movie star wardrobe. Ames also had a talent for outrageous self-promotion that doubtless increased tickets sales at his appearances. He came to Milwaukee many times as the star at high-priced night spots such as the Terris Club, Lakota’s and the Jay Jay Club.
The Jewel Box Revue was a drag show founded in 1939. The Revue was one of the first companies to bring cross-dressing performers to the public with openly gay men as its stars. The Jewel Box Revue review played for 26 weeks at the Tic Toc Club’s Gardenia Room and performed at Frank Balistrieri’s Club 26 and Brass Rail.
The Nuthouse on Sixth Street was successful as a “black-and-tan” club, meaning that whites as well as blacks were welcome. Neighbors complained that black-owned businesses belonged in the north side neighborhood known as Bronzeville, and the Nuthouse was shut down.
Today drag show entertainment in Milwaukee is more popular than ever, and top shows can be seen at Dix, Burnhearts, Cactus Club, Woody’s, Milwaukee Repertory Theater and other venues.

