Sherwood’s parents were Bob and Gail Sherwood. When they lived in Kokomo, Indiana, he 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 twelve years old, but later progressed to guitar and trumpet When he was twenty-two in 1933, he replaced Eddie Lang as the guitarist for Bing Crosby and remained with Crosby until the early 1940s. Beginning on October 2, 1940, he was the bandleader for Eddie Cantor’s radio program on NBC. During the same year, he was a regular on the “Hillman Hour” program on KFWB in Los Angeles, California.
Sherwood married Dorothy Virginia Gumm, the sister of Judy Garland, and worked as a bandleader for Garland during sessions at Decca Records.
He started a big band that included Dave Pell and Kitty Kallen. The band’s first single, “The Elk’s Parade”, a version of which is included on this CD was a million seller. He dabbled in acting but led his big band through the 1940s. In the mid-1940s, he hosted the radio program “Bobby Sherwood Orchestra” on the Mutual Broadcasting System and it is from those rare “live” recordings transcribed from the various locations that the band happened to be appearing that this CD comes. Sherwood died of cancer January 23, 1981, at his home in Auburn, Massachusetts.