Born in Birmingham, Alabama, it was while serving in the United States Army during and just after World War II, that Cheatham played in the 173rd Army Ground Force Band. Cheatham met his wife, Jean Evans, in 1956 in Buffalo, New York, when the local musicians' union chief called them separately to replace two musicians who could not make a job at the local Elks Ballroom. They married in 1959. Cheatham also taught jazz at Bennington College in Vermont and at the University of Wisconsin in Madison, Wisconsin.