Born Rudolph Richardson Riles in Memphis in 1924, Rudy was a young child when his family moved to Chicago.

After graduating from DuSable High, he entered the club scene and was continuously employed in Chicago by the most popular cabarets: Rudy's Chicken Shack, The Hurricane, Chicken Shack, El Casino, Rupneck’s, Kennedy's Honey Dripper Lounge.

Rudy's Early Career

An effeminate man, Rudy Richardson usually accompanied himself on the piano in the clubs, abd was often dubbed as "America's only male torch singer." Rim Records published his first singles with a release party scheduled for August 16, as advertised in a sizable display in the Chicago Defender.

Rudy's Hit Single: "Chauffeur"

“Chauffeur,” his main hit, was a torch song with a pleasant melody in which Richardson sang "I'm broken-hearted, so discarded" and, in the middle, in a spoken monologue “Chauffeur, take me home, I'm really gone... Don't think I'm wiggin', man, I'm just gone, you understand”.

Rudy's Late Career

Rudy released a single on Rim Records in June 1949, featuring "If You Get It" and "You Made My Heart Cry Out". He continued to appear fairly often in Chicago nightspots through the early 50s, including a long residency at the Kitty Kat Club.