Wilson joined the Jimmie Lunceford orchestra in 1939, replacing its star trumpeter and arranger Sy Oliver. While with Lunceford, he contributed numbers to the band's book, including "Hi Spook" and "Yard-dog Mazurka". Wilson has written arrangements for many other famous artists including Duke Ellington, Sarah Vaughan, Ray Charles, Julie London, Dizzy Gillespie, Ella Fitzgerald, Benny Carter, Lionel Hampton, Billie Holiday, Dinah Washington, Nancy Wilson and many more.