The first African-American to win an Academy Award got her big break in Milwaukee.

Before she made film history, Hattie McDaniel was working the hard roads as a touring performer. Born to former slaves in 1895 in Kansas, McDaniel had a natural talent for the stage and by age 20 she was working as a songwriter and singer. By the time of the Great Depression, she was based in Chicago as a part of an all-black touring ensemble. In January 1930, in Milwaukee doing a week-long engagement of Show Boat at the Davidson Theater, the company went broke and folded, leaving McDaniel out of cash and without work.

On a recommendation from a friend, McDaniel got a job as a ladies’ room attendant at the Club Madrid on Blue Mound Road in rural Waukesha County. The club was operated by Chicagoans Sam and Edward Pick and was frequented by high-rollers from the world of sports, politics and organized crime. Working nights, McDaniel made a dollar an evening, with another $2-3 in tips. Although it was “honest work” that came at a tough time in her life, McDaniel had ambitions that were far greater. She rented a flat on North Seventh Street and looked for work on the stage. “But no one seemed to need a colored singer,” she said.

Nor was McDaniel able to get Sam Pick to consider her for an act at the Madrid. “Then I told the porter that if he let the boss know I could sing, I’d grease his mitt.” The porter must have proven persuasive as the next Saturday, after the floor show ended early, Pick called for McDaniel. Still dressed in her maid’s uniform, she took the stage and had the band start into “The Saint Louis Blues.” The number brought down the house and nickels and dimes rained down on the stage from the appreciative audience. McDaniel later said that she took in over $100 in tips that night.

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McDaniel continued as a singer at the club – while still keeping her job in the ladies’ room – for the next few weeks. Pick eventually hired her on as a regular act and even sent her to Chicago to assemble an all-black backing cast. After about two years in the city. McDaniel moved to Los Angeles to join her brother and sister in trying to break into the movie business. She made her movie debut in 1932 and would end up appearing in 275 motion pictures.

McDaniel never forgot her Milwaukee roots… or her Milwaukee debts. In 1938, already well-established in the movies, McDaniel sent a letter to the Milwaukee Gas Light Company, with a check for an overdue bill totaling $2.87.

In 1939, McDaniel played the part of “Mammy” in Gone With the Wind, for which she would become the first African American to win an Academy Award. In 1947, reflecting on her career, she cited her time in Milwaukee as a turning point. “Milwaukee was really my springboard to Hollywood,” she said.

McDaniel died in 1952. She has since been honored with two stars on the Hollywood Walk of Fame (for radio and film) and has been featured on a U.S. postage stamp.