Starting sometime in the mid–80's, no one's quite sure, the Bosstones (as they were originally named) began merging their loves of punk, ska, metal and hardcore into songs. The start was slow, including an early hiatus for bassist Joe Gittleman and guitarist Nate Albert to finish high school, but came to fruition in 1990 with their debut Devil's Night Out. Following their genre–defining second album More Noise and Other Disturbances, the band jumped from Taang! and headed into the big leagues with Mercury Records. Their major label debut, Don't Know How To Party, is considered by many to be the defining album of their career and contains perennial fan favorites "Someday I Suppose" and "737", an ode to their P.O. Box in Cambridge that was used for fan mail for many years. Ska–core, the Devil and More gave a tongue–in–cheek name to the style they played, as well as giving the masses access to the standard live chant of "Mighty Mighty... ... Bosstones!"

On their 1994 release Question the Answers, the 'Tones took their sound in a harder, more raw direction. Incorporating more elements of hardcore, funk and a metric ton of feedback the band crafted their most eclectic release to date. Following this they released Let's Face It, exploding the 3rd wave of Ska into the mainstream with "The Impression That I Get." Now known as the "knock on wood" band by fratboys a'plenty, the band lay dormant for another 3 years, suffering member changes and a large amount of burnout. Pay Attention saw the departure of founding guitarist Nate Albert and shortly thereafter trombonist Dennis Brockenborough, as well as a more laid back sound, driving many longtime fans away, as well as not appealing to their radio audience the band seemed in dire straights. After being dropped by Island, the band sought refuge at Joe Sib's SideOneDummy, and released their final(–) opus, A Jackknife To A Swan. Jackknife saw a return to their harder roots, recalling memories of DKHTP and Let's Face It. Sadly, it seems to have been the band's last will and testament, as the various members have gone on to other projects, including Gittleman's Avoid One Thing, Albert's Kickovers, Brockenborough's Chubby and vocalist Dicky Barret's gig on Jimmy Kimmel Live.