Robert Lockwood, Jr. was born in Helena, Arkansas. He started playing the organ in his father's church at the age of 8. The great bluesman Robert Johnson, who allegedly sold his soul to the devil, lived with Lockwood's mother for 10 years off and on after his parent's divorce. Johnson taught Lockwood how to play the guitar.
Lockwood teamed up with Sonny Boy Williamson when he was 15 years old. The partnership lasted a couple of years before they split up. Lockwood moved to Chicago and got a record deal with Bluebird Records and split his time between St. Louis, Missouri, Chicago, Illinois, and Helena.
In 1941 they were featured on the very first King Biscuit Time radio show at the historic KFFA station in Helena. Lockwood and Williamson continued to be associated with King Biscuit Time for several years.
In the 1950s Lockwood played on Williamson's second Chess Records album which also included Willie Dixon and Otis Spann.
Lockwood was an early influence of B.B. King and played with King during his early career in Memphis, Tennessee.
In 1961 Lockwood moved to Cleveland, Ohio where he continues to reside.