Ernest Harold “Benny” Bailey (13 August 1925 – 14 April 2005) was an American jazz trumpeter.

A native of Cleveland, Ohio, Bailey briefly studied flute and piano before turning to trumpet. He attended the Cleveland Conservatory of Music. He was influenced by Cleveland native Tadd Dameron and had a significant influence on other Cleveland musicians, such as Albert Ayler, Bob Cunningham, Bobby Few, Bill Hardman, and Frank Wright. Bailey played with Tony Lovano, father of Joe Lovano.

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 remained in Europe and spent time in Sweden, where he worked with Harry Arnold‘s big band.He preferred big bands over small groups, and he became associated with several big bands in Europe, including the Kenny Clarke/Francy Boland Big Band. His time with Quincy Jones led to a brief return to the United States in 1960. He was invited to the studio as part of Freddie Redd‘s sextet to record Redd’s Blues after meeting the pianist during a tour in Sweden. He returned to Europe, first to Germany, then the Netherlands, where he settled permanently.

In 1969 he played on Eddie Harris and Les McCann‘s album Swiss Movement, recorded live at the Montreux Jazz Festival, although it was not his usual style of music. In 1988 he worked with British clarinetist Tony Coe and recorded albums until 2000 when he was in his mid-70s. Bailey died at home in Amsterdam on April 14, 2005.