Billie Holiday Monument, Baltimore Jazz

Billie Holiday Monument on Pennsylvania Avenue

Baltimore Jazz

Baltimore has given the entertainment world such Jazz legends as Eubie Blake, Chick Webb, Cab Calloway and Billie Holiday. Blake co-wrote the first Black musical on Broadway. Chick Webb, Cab Calloway and Billie Holiday were legendary performers on Pennsylvania Avenue, the Chitlin’ Circuit and stages/nightclubs worldwide.

The Avenue’s cultural reputation escalated in 1922, as the black-owned Douglass Theater opened. A few years later the 1,000-seat theater was sold to European Americans and name-changed to the Royal Theater. Also in the 1920s, the Regent Theater opened. Seating 2,000 patrons, it was a grand vaudeville and movie house, famous for music and dance revues with chorus lines comparable to the Cotton Club. The Avenue had become was such a cultural magnet that the first talking movie in Baltimore was shown at the Royal Theater in 1929.

Royal Theater became a mainstay on the Chitlin Circuit, which included the Apollo in Harlem, Regal in Chicago, Howard in Washington, Paradise in Detroit and the Earl in Philadelphia. Ethel Waters got her start at the Royal and Pearl Bailey sang in a chorus line. The biggest stars in black entertainment performed at the Royal, including Louis Armstrong, Ethel Waters, Chick Webb, Fats Waller, Cab Calloway, Louis Jordan, Nat King Cole, Duke Ellington, Billie Holiday, Pearl Bailey, Count Basie, Platters, Sam Cooke, Temptations and Supremes. Every show night, a procession of Cadillacs and Lincolns lined up for blocks before arriving at the Royal Theater.

The Avenue had a solid roster of additional nightclubs, highlighted by the nationally famous Sphinx and Gamby’s, whose after-parties were “Off the Chain.” Imagine partying with Billie Holiday, Pearl Bailey Duke Ellington and Sam Cooke just after a performance!

With such a tradition to draw from, it is rather surprising that Baltimore’s musical torch is only being carried forward nationally by performing artists Toni Braxton and Dru Hill. Before moving to Oakland, Tupac Shakur (1971-1996) attended Baltimore School for the Performing Arts to study acting and ballet. Even then, his teachers said he showed tremendous potential.


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