The group came together in the early 1950s in Detroit and initially called themselves the Del-Torros. The members were Charles Evans (bass), James Drayton (baritone), Lonnie Heard (tenor), and Eddie Hurt (lead tenor) also known as Little Eddie. By the time the group came to Fortune studios to audition in 1955, they had added a fifth member, Richard Lawrence, and had also changed their name to the Five Dollars. The name change had come about at the suggestion of one of the Spaniels, whom the group had met on a trip to Chicago. The raw gutsy sound of the Five Dollars was probably well-matched with Fortune Studios. With Fortune's primitive recording environment, the group didn't have to worry for a moment about being over-produced. On August 20 of 1955, Devora Brown of Fortune Records announced the signing of the Five Dollars. In the same press release, she also said that Andre Williams had been signed by Fortune, both as a singles artist and also as part of the Five Dollars. This last part came as shock to the Five Dollars. Andre Williams and Eddie Hurt were in-laws, being married to two sisters. How Williams became married to the Five Dollars remains a mystery. It certainly wasn't a match made in heaven, but appears to have been orchestrated behind closed doors at Fortune. Williams did not record as part of the Five Dollars, although they did back him up on several recordings under their Don Juans' alter ego.
The groups' last release for Fortune was in 1960, My Baby-O paired with That's the Way It Goes. The group continued to perform for some time in the '60s, but eventually decided to end their run at show business success. As of 2002, Eddie Hurt and Richard Lawrence are deceased. Charles Evans, Lonnie Heard, and James Drayton still reside in the Detroit area. Although never a national success, the Five Dollars/Don Juans made their mark as one of the most important of Detroit's pre-Motown vocal groups.