Henderson kicked off his music career in his native Chicago, Illinois in 1952, when he performed with Grammy winner Ramsey Lewis' acclaimed trio. He later moved to New York to pursue a recording career, and made albums as a Vee-Jay record label artist.

Through his partnership with the company, he worked with greats such as Count Basie, Oscar Peterson, and Eddie Harris, and he later teamed with Blue Note Records for Senor Blues, which became one of the biggest-selling singles in the label’s history.

Henderson also collaborated with the likes of Dizzy Gillespie, the Charlie Haden Quintet, Frank Sinatra, Tony Bennett, and Quincy Jones throughout his career.

In 1967, his good friend Bill Cosby suggested Henderson pursue an acting career, and he relocated to Hollywood.

Henderson appeared in films such as Clue, Fletch, City Slickers, White Men Can't Jump, Maverick, Ghosts of Mississippi, and Lethal Weapon 4. His TV credits included ER, Hill Street Blues, Happy Days, The Jeffersons, MACGyver, NYPD Blue and My Name Is Earl.