Roosevelt Sykes was born on 31/01/1906 in Elmar, Arkansas. He grew up in Helena, Arkansas. When he was 15, Sykes left home and went on the road playing barrelhouse blues on the piano. He travelled to various sawmill, turpentine and levee camps along the Mississippi River and eventually ended up in St Louis, Missouri. There he met St Louis Jimmy Oden.
In 1929, Sykes was spotted by a talent scout and went to New York to record for Okeh Records. In the same year, he released his first record the song "44 Blues". He recorded for various labels and used various names including Easy Papa Johnson, Dobby Bragg and Willie Kelly for Victor Records (1930 to 1933).
Sykes would become friend with Charlie "Specks" McFadden and Sykes accompanied him on half of his recordings.
In 1934, Sykes signed with Decca Records after he and St Louis Jimmy Oden moved to Chicago.
In 1943, Sykes signed with Bluebird Records and recorded with The Honeydrippers. Sykes and Oden would continue to play music together into the 1960s.
In Chicago, Sykes starting using an eight bar blues pop gospel structure instead of a twelve-bar structure. After his RCA Victor contract expired he continued to work for smaller labels until he could no longer find labels in the mid-1950s as his style became less popular.
In 1954, Sykes left Chicago and moved to New Orleans. He returned to recording in the 1960s and recorded for labels such as Delmark, Bluesville, Storyville and Folkways.
He spent the remaining part of his life living in New Orleans.
On 17/07/1983, Sykes died of a heart attack in New Orleans.
In 1999, he was posthumously inducted into the Blues Hall of Fame.
In 2011, he was posthumously inducted into the Gennett Records Walk of Fame.