Ernest Harold “Benny” Bailey (August 13, 1925 – April 14, 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 B 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, and played at the 1960 Newport Jazz Festival. He returned to Europe, first to Germany, then the Netherlands, where he settled permanently.