Formed in Brooklyn, NY, the group originally consisted of Eugene Pitt (lead), Jerome Hanna (tenor), Richard Harris (tenor), Billy Prophet (baritone), and Norman Johnson (bass). The Jive Five's first hit, "My True Story," was their biggest, peaking at number one on the R&B charts and number three on the pop charts in the summer of 1961. None of the band's subsequent singles -- including 1962's minor R&B hit "These Golden Rings" -- were as popular, but the group managed to keep performing and recording. Under the direction of Eugene Pitt and Norman Johnson, the Jive Five refashioned themselves as a soul band in 1964, forming a new lineup with Casey Spencer (tenor), Webster Harris (tenor), and Beatrice Best (baritone). This new incarnation of the band signed to United Artists Records. The group only had one hit on UA, 1965's "I'm a Happy Man."

In 1966, the Jive Five left United Artists and signed with Musicor, where they had the 1968 R&B hit "Sugar (Don't Take Away My Candy)." They changed labels again in 1970, signing with Decca. That same year, they changed their name to the Jyve Fyve, in order to appear more contemporary. The Jyve Fyve had only one minor R&B hit, 1970's "I Want You to Be My Baby."

The group continued to perform and record for a variety of small labels during the '70s, but never had another hit. Throughout the '70s and '80s, the only constant member was Eugene Pitt. In 1975, Pitt changed the name of the group to Ebony, Ivory & Jade, but this new incarnation failed to gain much attention. In 1982 Pitt changed the name of the group back to the Jive Five and the band recorded two albums for the indie label Ambient Sound. Across the following decades the Jive Five were regulars on the oldies circuit, and in 2003 they issued a CD single (under the moniker Eugene Pitt & the Jive Five) entitled "It's Christmas" on Doesn't Matter Music.