Benny Bailey (born Ernest Harold Bailey 13 August 1925 in Cleveland, Ohio – 14 April 2005 in Amsterdam) was an American Bebop and Hard bop jazz trumpeter.

He 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 band's 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. He died at home in Amsterdam on April 15, 2005.

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