The year was 1937, and the first role offered Eddie Anderson on The Jack Benny Program on radio was that of a Pullman porter. It was to be a one-time part, but there was something about the gravely-voiced African-American actor that led the producers to use him again first as a waiter, and another time as a fellow who has an altercation with the star, Jack Benny. Benny realized that Anderson could be so much more than a stereotype.
Jack Benny changed the character of Rochester from a near stereotype to a much more positive and affirmative character, but in his own way he also stood up against segregation on behalf of Eddie Anderson. Once Eddie Anderson was denied a room in a hotel in St. Joseph, Missouri at which Jack Benny's cast and crew had planned to stay, Jack Benny told them, "If he doesn't stay, neither then do I." The hotel relented and gave Eddie Anderson a room.
The South was not the only place where racism against Eddie Anderson took place. Once in New York, a couple at a hotel at which the cast and crew were staying complained about being in the same hotel as Eddie Anderson. The hotel manager tried to convince Eddie Anderson to move to another hotel. The show's producer and Mary Livingstone's brother (Livingstone was Benny's wife,) Hilliard Marks, told the manager that Eddie Anderson would be happy to move to another hotel. The following day the entire cast and crew, 44 people in all, checked out of the hotel.
In the end Jack Benny and Eddie Anderson became a comedy team, much in the same way that Bob Hope and Bing Crosby or George Burns and Gracie Allen were. What made them a success as a team was not simply that they were two very talented men, but that they were also very close friends who were quite comfortable with each other.