Bailey had some training in piano and flute in his youth, but switched to trumpet, and concentrated on the instrument while at the Cleveland Institute of Music. In the early 1940s he worked with Bull Moose Jackson and Scatman Crothers. He later worked with Dizzy Gillespie and toured with Lionel Hampton. During a European tour with Hampton he decided to stay in Europe and spend time in Sweden. This Swedish period saw him working with Harry Arnold's big band. He tended to prefer big bands over small groups and became associated with several big bands in Europe including The Kenny Clarke-Francy Boland Big Band. Later he began to work with Quincy Jones and that led to a brief return to the United States in 1960. After that he migrated to Germany, and later the Netherlands.
In 1969 he played on Eddie Harris and Les McCann's album Swiss Movement which was recorded live at the Montreux Jazz Festival, even though it was not normally his style of music. Then in 1988 he worked with Tony Coe and he kept producing albums until 2000 when he was in his mid-70s.
Bailey died at home in Amsterdam on April 14, 2005.
- Bennie Bailey Plays (Argo 1959)
- Big Brass (Candid 1960)
- Stockholm Sojourn (Concord 1964)
- Soul Eyes - (MPS 1968)
- Folklore In Swing (MPS 1966)
- The Balkan In My Soul(MPS 1968)
- Soul Eyes: Jazz Live at the Domicile Munich (MPS 1968)
- Mirrors (The Amazing Benny Bailey) (arranged & conducted by Francy Boland (Freedom 1971)
- Islands (Enja 1976)
- Serenade to a Planet (Ego 1976)
- East of Isar (Ego 1978) - The Sal Nistico-Benny Bailey Quintet
- Grand Slam (Jazzcraft 1978)
- While My Lady Sleeps (Gemini 1990)
- No Refill (TCB Records1994)
- Angel Eyes (Laika 1995)
- Peruvian Nights (TCB 1996)
- I Thought About You (Laika 1996)
- The Satchmo Legacy (Enja 2000)