Reeves started out playing locally in the Midwest; he moved to New York City in 1924 and then to Chicago in 1925. In 1926 he joined Erskine Tate's orchestra, then played with Fess Williams and Dave Peyton (1928-1930). He signed to Vocalion and recorded as a bandleader with his groups the Tributaries and the River Boys; among his sidemen were his brother, trombonist Gerald Reeves, and clarinetist Omer Simeon (20 sides were recorded in 1929). He played under Cab Calloway in 1931-32, and recorded again with the River Boys in 1933. He toured as a leader from 1933–35, then played freelance through the late 1930s. During World War II, he led an Army band called the Jungleers. Stationed at the Army Jungle Training Center on the northeast coast of Oahu, they were popular participants in Battle of the Band competitions that were an integral part of the "extraordinary music scene in Hawaii during the war."  After the war, he played in Harry Dial's Blusicians in 1946.
- Albright, Alex. The Forgotten First: B-1 and the Integration of the Modern Navy, Fountain, NC: R.A. Fountain, 2013: 115-116.