He appeared in three films including Pal Joey in 1957. Sherwood"s parents were Bob and Gail Sherwood. When they lived in Kokomo, Indiana, Bob Sherwood operated a movie theater and Gail Sherwood "organized an orchestra which was among the first ones to play popular syncopated music" Bobby Sherwood began playing banjo with that group when he was 12 years old.
Radio Beginning October 2, 1940, Sherwood was the bandleader on Eddie Cantor"s program on National Broadcasting Company. That same year, he was a regular on the Hillman Hour program on KFWB in Los Angeles, California.
In the mid-1940s, he had his own program, Bobby Sherwood Orchestra on the Mutual Broadcasting System. In 1953, he had a daily early morning program on WJZ, in New York City, and at one time he had a disc jockey show on WNEW (also in New York City).
He hosted the DuMont Network variety show Stars on Parade (1953-1954), was the announcer for DuMont"s The Morey Amsterdam Show, and the host for the American Broadcasting Company game show Quick as a Flash (March to May 1953). Sherwood has a star at 1825 Vine Street, in the section of the Hollywood Walk of Fame.
Sherwood died of cancer January 23, 1981, at his home in Auburn, Massachusetts.