The song was loosely based on Bobby's brother's carefree behavior and was originally recorded as a funny tribute to his brother, that turned tragic when Harry Womack was killed by his girlfriend during a fight in 1974.
From then on until his death, Bobby Womack sung the song as a dedication to his fallen late brother.
[1] Womack explains the story behind the song and its aftermath: "Harry was the bass player and tenor for the brothers when we were the Valentinos.
Previously I had hired a new bass player because I felt it would help Harry's relationship with his spouse if he wasn't on the road.
At that time, "Harry Hippie" wasn't a joke anymore; I had lost a brother.