Cab Calloway was a famous African-American jazz singer, dancer and bandleader, recognized in the Grammy Hall of Fame, who performed at the speakeasy Ball & Chain in what is now called Little Havana. He also performed regularly at the famous Cotton Club in Harlem, New York. 

From the 1930s to the late 1940s, Calloway led one of the most popular big bands in the United States, featuring performers like Dizzy Gillespie, who played a key role in the development of Afro-Cuban jazz. His most famous song was “Minnie the Moocher,” recorded in 1931. By the time he died at age 86, Calloway had made numerous appearances on stage, film and television. He also influenced Michael Jackson and other hip-hop performances. 

During segregation, Calloway, like other black entertainers, was not allowed to stay at hotels in Miami or Miami Beach — except for those in what was then called Colored Town (now called Overtown). In Miami’s Overtown, he performed at clubs like Rockland, Palace, the Harlem Square Club, the Cotton Club, the Ritz Theater, the Mary Elizabeth Hotel and the Sir John. It is possible, however, that he was also snuck into the Tower Hotel in what is now Little Havana, because the Jewish owner — Henry Schechtman — thought it ridiculous that black performers would have to head all the way back to Overtown at 5 o’clock in the morning, after late night gigs.

Calloway was the first African American musician to sell a million records from a single song and to have a nationally syndicated radio show. He is also in the  Grammy Hall of Fame and received the Grammy Lifetime Achievement Award.