(Text and photos by Michail Takach, for an historical panel created by this project in 2019. The panel is on loan to the 'This Is It' bar in downtown Milwaukee.)

"The floor show is on, and it’s something unusual for Milwaukee entertainment: female impersonators."

On November 19, 1933, the Milwaukee Sentinel began a four-part expose on "midnight to dawn clubs," which had seen explosive growth in the final days of Prohibition. "Lights Burn Brightest Long After Curfew; Spots Range from Gay Clubs to Low Dives," shouted the headlines, as the reporters visited the gayest club of all, Club La Tosca (516 E. Detroit St., now St. Paul at Jefferson.)

One of those impersonators was Billy (aka Billie) Herrero, famously known as "the Brazilian Gypsy Rose Lee," "the Brazilian Carmen Miranda," and later, "Senorita Herrero, the Brazilian Sensation." Abandoned by his unwed mother, Billy overcame his orphanage childhood to tour the world as an international drag superstar.

As a 9-year-old child living in Los Angeles, Herrero was inspired by the farewell performance of Julian Eltinge, the wealthiest female impersonator of the vaudeville era. He later claimed to have been trained in dance, dress and "womanhood" by Rita Hayworth herself.

Herrero was only 15 when he started performing in the Third Ward’s cut-rate cabarets. It’s unclear what brought him to Milwaukee, but it seems he made his drag debut here. He was known for his Dolores Del Rio, Hedy Lamarr and Pola Negri acts. When cross-dressing was criminalized, Billy moved to San Francisco to perform at the famous Finocchio’s.

Twelve years later, Billie Herrero returned to Milwaukee to steal the spotlight. His rendition of Gypsy Rose Lee was so perfect that audiences thought they were watching the real actress. In fact, Gypsy’s former nanny traveled to Milwaukee to see the show — and left believing that Gypsy Rose Lee had been a man all along.

By 1950, Billie was making over $3,000 per week in downtown Milwaukee. "Billie Herrero made over a million dollars in her day," he would later lament, "but she spent it all on luxuries."

Then he made a huge mistake: on a dare, he invited the real Gypsy Rose Lee to come see him, thinking she would be flattered. "I won’t have it," she declared from her front row seat, two minutes into the show. "How dare you? I'll sue you." Her lawyers backed up the threat. "A cheaper version of Gypsy Rose Lee threatens her livelihood," they argued. (The opposite was actually true: clubs that sold out for Billie Herrero saw smaller crowds when they booked the real Gypsy Rose Lee!) With nine weeks left in her contract, Billie was terminated October 25, 1950. It seems her last show was at Club 26 (2601 W. North Avenue) on New Year's Eve, 1953.

By 1954, Herrero was broke and fed up with nightlife. He retired from entertainment, went back to being "Billy," and relocated to Florida. Rich with clutter, he operated an antiques shop in Coconut Grove for many years.

Old age was not kind to the former sensation. Deeply depressed, going blind, facing eviction, and over $500,000 in debt, Billy set his home on fire and committed suicide on Christmas Eve, 1992. A large coffee table book, titled "How to Live a Victorious Life," was one of the only survivors of the fire. His collection of show business memorabilia, dating back six decades, was sold at auction.

There was no memorial service for Billy. He had few friends and no surviving family. Untrusting of the world since childhood, he had never allowed himself to be romantic. Most of his co-workers and fans had already passed away.

"I've enjoyed the company of dignitaries and degenerates," he told a Miami magazine shortly before his suicide. "I have had an amazing life."