Born to Big Ed Anderson, a minstrel performer, and Ella Mae, a circus tightrope walker, Eddie “Rochester” Anderson had performing in his blood. He was born in Oakland, CA on September 18, 1902 and got his start in vaudeville. He also appeared in films and, in 1937, debuted as the voice of a Pullman porter (that’s an employee who works on a train, specifically in a sleeper car) on Jack Benny’s popular radio show, The Jack Benny Program. He was originally to appear only once on the show; however, audiences loved him so much that he became a regular cast member and the first black performer to have a regular part on radio. The show transitioned to TV as the character “Rochester van Jones” or, more popularly known as just “Rochester”, Anderson would deflate Benny’s pretentiousness with a high-pitched, incredulous, “What’s that, boss?”
By 1942, Anderson was earning $100,000 a year making him the highest-paid black actor in Hollywood for a while. Converted to 2012 dollars, that’s $1,389,662.28 a year. He was smart with his money, made wise investments that yielded him great returns and he became extremely wealthy.
Anderson had a part in Gone with the Wind as Uncle Peter, and movies Cabin in the Sky, and Stanley Kramer’s It’s a Mad, Mad, Mad, Mad World. He passed away in 1977 from heart disease in Los Angeles, CA, and was inducted into the Radio Hall of Fame in 2001.
Here’s a clip of Anderson singing on The Jack Benny Program where he shows off his dancing moves too. Unfortunately, I don’t know what year this aired; probably some time in the 1950s.
Biographical information gathered from here.