The band’s roots lay in the hardcore punk scene of the early 1980s, along with strong influences from the British 2 Tone ska scene of the late 1970s. Barrett was the singer for up-and-coming Boston thrashers Impact Unit and knew Burton and Bridwell from their hardcore band Dx:A, with whom he shared a rehearsal space. In 1984 Barrett and Bridwell were members of The Cheapskates, a loosely formed punk all-star band made up of members of Gang Green, Jerry’s Kids, Stranglehold and Mission Impossible. Another member of both The Cheapskates and Mission Impossible was longtime and current BossTones collaborator, keyboardist John “JG” Geotchius. Under Barrett’s guidance, The Cheapskates’ were an attempt at 2 Tone style ska. But with all the members coming out of the hardcore punk scene it was inevitable that the band would have a harder edge and rowdier persona. When The Cheapskates began to fizzle due to lack of commitment from the various members, Barrett was approached by Gittleman, Albert and Carr, friends who were attending Cambridge Rindge and Latin High School. They asked if he would front the ska band they were trying to get off the ground. The core lineup coalesced around Barrett, Gittleman (bass), Albert (guitar), Josh Dalsimer (drums), and Bridwell (trumpet.)Burton (saxophone), who had been living on a sailboat in Florida, joined after the first couple gigs. At an early gig, Carr, who had been functioning as more of a roadie and drinking buddy, was denied entrance to the club because he was under-age. Barrett convinced the club owner that Carr was actually in the band. To keep the club off their backs, Carr joined the band on stage, danced and sang back-up. He has been a member ever since. Another early member was Davey Holmes, a friend of Dalsimer’s from Brookline High School. Holmes played with the band for about a year and is in the group photo on the back of the Devils Night Out album. After almost naming themselves “The Cashmeres,” the group decided on the, “The BossToneS,” as a tribute to their hometown.
In 1987 The BossToneS made their recording debut when they were featured on the Mash It Up ska compilation. Their contribution was “The Cave.” Another early recording, “Drums and Chickens,” appeared on the compilation Mashin’ Up The Nation. By the time Mashin’ Up The Nation was released however, the band had disbanded, primarily so Albert could finish high school. During this time Gittleman joined hardcore legends Gang Green. Gang Green had recently been embraced by a large audience within the heavy metal mainstream. Gang Green went on several high profile tours and were signed to a mid-level record label. In 1989, after several years of hard touring, hard drinking, and ultimately bad feelings, Gittleman was fired from Gang Green. Feeling bad for his friend, Barrett suggested they get The BossToneS back together.