Jackson played in Detroit in the 1940s with Thad Jones, Tommy Flanagan, and Wardell Gray, and had a variety show with Eddie Locke called Bop & Locke. After working with Yusef Lateef from 1954–56 he moved to New York, where he played regularly at the Metropole in 1957–58. Following this he worked with Teddy Wilson, Charlie Shavers (1959–61), Buck Clayton, Benny Goodman (1962), Lionel Hampton (1962–64), Kenny Burrell, Earl Hines (1964–70 intermittently) and the JPJ Quartet with Budd Johnson. Later in life he played with Sy Oliver (1975–80), Oscar Peterson, and George Wein's Newport All-Stars. As a bandleader, Jackson led a 1961 date in Switzerland and recorded at least five albums for Black & Blue Records between 1977 and 1984.
His brother, bassist Ali Jackson, performed with him both at the beginning and towards the end of their careers.
Jackson died from heart failure at the age of 61.
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- As leader/co-leader
- 1984: Billy's Bounce - Oliver Jackson Quintet (Oliver Jackson, Ali Jackson on bass, Irvin Stokes on trumpet; Norris Turney on alto sax, and Claude Black on piano)
- As sideman
With Gene Ammons
- Bad! Bossa Nova (Prestige, 1962)
With Kenny Burrell
- The Tender Gender (Cadet, 1966)
With Dexter Gordon
With Illinois Jacquet
- The Blues; That's Me! (Prestige, 1969)
With Etta Jones
- Love Shout (Prestige, 1963)
With Yusef Lateef
- Jazz and the Sounds of Nature (Savoy, 1957)
- Prayer to the East (Savoy, 1957)
- The Sounds of Yusef (Prestige, 1957)
- Other Sounds (New Jazz, 1957)
- Cry! - Tender (New Jazz, 1957)
With Gildo Mahones
- I'm Shooting High (Prestige, 1963)