[1][2][3] From the band's inception, lead vocalist Dicky Barrett, bassist Joe Gittleman, tenor saxophonist Tim "Johnny Vegas" Burton and dancer ("Bosstone") Ben Carr remained constant members.

The band's final line-up also included drummer Joe Sirois, saxophonist Leon Silva, guitarist Lawrence Katz, keyboardist John Goetchius, and trombonist Chris Rhodes.

[8] Bassist Joe Gittleman played with local hardcore band Gang Green, while vocalist Dicky Barrett was a member of Impact Unit and, later on, Cheapskates.

By the time Mashin' Up The Nation was released, the Bosstones had temporarily disbanded in order for Albert and Gittleman to finish high school.

[8] The album was released to positive local and lukewarm national reaction during a time when ska was struggling to move out of the American underground.

[8] Four of the seven tracks paid homage to the band's influences: The Angry Samoans' "Lights Out", Minor Threat's "Think Again", SSD's "Police Beat" and The Wailers' "Simmer Down".

Produced by Tony Platt, the band's third LP, Don't Know How to Party contained a cover of Stiff Little Fingers' song "Tin Soldiers" as well as a vocal appearance by Daryl Jennifer of Bad Brains.

Besides touring, the band found itself making their network television debut on The Jon Stewart Show and hosting MTV's 120 Minutes.

Released in 1997, Let's Face It, would prove to be the band's biggest seller, mostly due to its first single "The Impression That I Get", which reached number one on the Billboard Modern Rock Tracks chart.

The mainstream exposure led to the band's appearance on Sesame Street's Elmopalooza television special and Grammy Award-winning soundtrack album, in which they performed the song "The Zig Zag Dance" with The Count.

The album was recorded live in Cambridge, Massachusetts at The Middle East Restaurant and Nightclub during the band's annual end-of-the-year Hometown Throwdown from 1997.

In 1999, the band contributed their cover version of the song, "Rudie Can't Fail," to the Burning London Clash tribute compilation.

After the recording of Pay Attention, founding member Nate Albert left in order to obtain a degree in political theory from Brown University.

His next musical venture would be as a member of Evan Dando’s re-formed Lemonheads before forming The Kickovers, which focused more on a 1970's punk sound than ska.

[9] Before the hiatus announcement, Gittleman had already formed a side project band named Avoid One Thing featuring members of Darkbuster, the Raging Teens and Spring Heeled Jack.

Sirois recorded and toured with Nate Albert's next band, Kickovers, and also played drums for the Street Dogs and Frank Black.

He also performed with former Spring Heeled Jack bandmate Rick Omonte in The Mountain Movers and as a fill-in trombonist for Less Than Jake, Reel Big Fish, and NOFX.

Katz has also played guitar on several motion picture soundtracks including Aquamarine, The Good Night and London, the latter recorded in collaboration with The Crystal Method.

During an Alternative Press Acoustic Session, members of fellow Boston area ska band Big D and the Kids Table hinted that the Bosstones were in fact reuniting for another Hometown Throwdown.

Soon after Barrett's announcement, Gittleman declared that the band intended to record three new songs to be included on an upcoming collection of unreleased material and vinyl B-sides.

At two of the March shows in Las Vegas and Los Angeles, Jimmy Kimmel served as a guest star on bass clarinet during "The Impression That I Get".

On October 16, 2009, the album title was announced to be Pin Points and Gin Joints and a free download of the song "Graffiti Worth Reading" was made available.

The band continued to tour through the summer of 2009 with shows in Buffalo, New York, Providence, Rhode Island, Asbury Park, New Jersey, Seattle, Washington, San Francisco, California, Anaheim, California, Hampton Beach, New Hampshire, and Victoria, British Columbia where they performed at the Victoria Ska Fest with Voodoo Glow Skulls, The Slackers and Chris Murray.

March 2017 saw the release of their first recording in six years with a limited edition vinyl 7" featuring a cover version of the Burt Bacharach song, "What the World Needs Now Is Love" backed with the track "I Won’t Go Out Like That".

In September 2017, Tim Burton announced in a post Riot Fest interview that the band was working on a new album set for release in early 2018.

According to guitarist Lawrence Katz and producer Ted Hutt's Instagram accounts, recording started on Friday, November 17 at Kingsize Soundlabs in Los Angeles, California.

To temporarily fill in for Silva, the band brought in Roman Fleysher[16] and Peter "JR" Wasilewski of Less Than Jake to play saxophone on select dates.

In conjunction with the announcement, the band released a new single titled, "The Final Parade" which features guest appearances by Jamaican singer Stranger Cole and members of Rancid, The Interrupters, Fishbone, Stiff Little Fingers, The Suicide Machines, Less Than Jake, Murphy's Law, H2O, Goldfinger, Sonic Boom Six, The Toasters, Bim Skala Bim, Big D and the Kids Table, Doped Up Dollies, The Aggrolites, Dance Hall Crashers, The Aquabats, Buck-O-Nine, The Porkers, The Pietasters, Los Skanarles, Buster Shuffle, Kemuri, Big Bad Voodoo Daddy, and The Specials.

"[7] Although the band chose to keep their reasoning for the split private, speculation suggested that it was over Barrett's stance on COVID-19 vaccines[20] and his participation in the production of a video promoting the "Defeat the Mandates" anti-vaccination mandate rally held by Robert F. Kennedy Jr.[21] In February 2022, Barrett was a guest on The Highwire with Del Bigtree podcast where he confirmed that it was his anti-vaccination views that had made the rest of the band uncomfortable.

[28] The Tampa Bay Times described it similarly as an "eclectic swirl of good-time music fuses the perky pick-it-up sound of pre-reggae ska with monstrous hard-core guitars.