[2] While studying at Shorter College he met Alphonse Trent, and began arranging material for him.
From 1924 to 1926 he led his own ensemble; later in 1926 he played with Speed Webb, and in 1927 he spent time with Mutt Carey's Jeffersonians and Paul Howard's Quality Serenaders.
In addition, in the second half of 1929 this ensemble was joined by Leroy Carr and Scrapper Blackwell, issuing a small number of recordings billed as the Famous Hokum Boys.
[2] There he arranged for Paul Whiteman, Benny Carter, Claude Hopkins, Andy Kirk, Ina Ray Hutton, the Mills Blue Rhythm Orchestra, and Duke Ellington.
Hill again put together his own group in 1935, but after playing at the Savoy Ballroom, he disbanded the ensemble due to his tuberculosis.