Bobby was born in Indiana and may have inherited his show business talent from his grandfather who played the alto horn and disappeared- never to be seen since-with a carnival that was passing thru Indiana. Bobby, who is multi-talented, recorded a song called "Yes Indeed", in which he plays ten instruments, sings all four voices of the quartet, sings the solo, and also arranged the song. Sherwood's father was a singer and trambone player and his mother was a pianist. They had a vaudeville act called Bob-Gayle Sherwood & Co. Bobby joined the act when he was ten singing , dancing, and playing the banjo. Playing the horse was a favorite pastime of Bobby's. To quote "I didn't learn much about history and arithmetic, but I could tell you the best time of any horse at any track.". After vaudeville folded, Bobby played in clubs around Los Angeles, and became Bing Crosby's accompanist on records, in the band, in movies, and on radio. He later played on radio shows with Burns and Allen, Al Jolson, Rudy Vallee, Edie Cantor, and many more. Later he formed his own band, and starting appearing on television getting his first taste in Cleveland in 1948 appearing in everything from straight dramatic roles to a straight man for top comedians.