His best known song is "Let Me Go Home, Whiskey", which was a hit in the early 1950s for Amos Milburn and was later revived by Asleep at the Wheel. Another Henry song, "Hyping Woman Blues", recorded by T-Bone Walker was sampled by DJ Mr. Scruff for his song "Get a Move On", which was used in several TV commercials. This led to a revival of interest in Henry's compositions.
Henry recorded with and arranged for the elite of jazz and rhythm and blues, including Dinah Washington, Billy Eckstine, Dizzy Gillespie, Charles Mingus, The Treniers, Illinois Jacquet, and Miles Davis. Henry maintained strong social as well as professional relations throughout the city and the music industry. The Shifty Henry All-Stars played regularly at New Year's Eve balls thrown by socialite Dorothy Chandler and her husband Otis, publisher of the Los Angeles Times.
Leo Fender selected Henry to receive an early electric Fender Precision Bass. Henry appears as a string bass player in a jazz club, in the film noir movie, D.O.A. in 1950. He also played in the house band for the Martin and Lewis television show.