Oakley was born in Chicago, IL, raised in the suburb of Park Forest, IL, then moved to Florida where he joined Dickey Betts’ band, The Second Coming. He was a founding member of The Allman Brothers Band in 1969, along with guitarist Duane Allman, Gregg Allman, who was the band’s vocalist and keyboardist, Dickey Betts on co-lead guitar, and drummers Butch Trucks and Jai Johanny “Jaimoe” Johanson.
With the Allman Brothers, Oakley was known for his long, melodic bass runs underneath Allman and Betts’ furious guitar solos and jams.
“In Memory of Elizabeth Reed,” “Mountain Jam” and “Whipping Post” from the live album At Fillmore East capture Oakley at his best. Oakley was also the band member most involved in establishing domestic unity among the group’s extended family. When Duane Allman died in a motorcycle accident, Oakley was devastated, according to drummer Butch Trucks. The band continued touring, but Oakley “lost his sparkle” and started drinking heavily during what was to become his last year in life.