In 1993 the BossToneS signed a contract with major label Mercury Records. This was the first contract they had ever signed. Taang! Records had tried to get the band to sign contracts giving the label 100% ownership of their recording, publishing and merchandise rights. The band never signed, jokingly referring to themselves as, “The band without a pen.” They had been courted by several labels but ultimately decided on Mercury due in large part to friend Alec Peters being on the Mercury staff. Peters promoted shows during the early days of Boston’s hardcore scene and managed Gang Green during Gittleman’s time with the band. He would become the BossToneS A&R representative at Mercury.
Soon after joining Mercury the band released the Ska-Core, the Devil, and More EP. Released in March 1993, it was largely a collection of cover songs. In interviews the band said the songs chosen where meant to send a message to the label. The covers were The Angry Samoans “Lights out,” Minor Threat’s “Think Again,” SS Decontrol’s “Police Beat,” and The Wailers’ “Simmer Down.” The EP contained one new studio track, “Someday I Suppose,” as well as three live tracks.
The BossToneS’ third album was 1993’s Don’t Know How to Party. The album was produced by Tony Platt, whom the band selected because of his work with AC/DC, Bob Marley, Motorhead and Cheap Trick, among others. The song “Someday I Suppose” was also included on the album and a video was shot for the song. The footage had originally been intended to be used as promo material for their Mercury debut, but the label liked the footage and turned it into a single. The video received minor airplay on MTV and the song reached # 19 on the US rock charts. The band would also appear on the 1994 Kiss My Ass tribute to Kiss album with a cover of “Detroit Rock City.” Mercury released the song as a single, with the b-side featuring the original Kiss version. Soon after the band was invited to open up for Aerosmith at their New Year’s Eve concerts at the Boston Garden.
Around this time the band started their own label, Big Rig Records. They wanted to release their albums on vinyl. Mercury was no longer printing vinyl and partnered with the band to start the label for this purpose. Mercury continued to handle the conventional CD and cassette versions of the albums while Big Rig focused on vinyl editions. The new label immediately issued re-releases of Don’t Know How to Party and Ska-Core, the Devil and More on colored vinyl. Later releases include a CD re-release of Barrett’s former hardcore band Impact Unit.
The BossToneS released their fourth album, Question the Answers, in October 1994. Recorded at studios in Philadelphia, Boston and Woodstock, New York, the album featured production work by the Butcher Brothers, Paul Q. Kolderie and Ross Humphrey. The Big Rig vinyl version of the album contained an extra track titled “Pirate Ship.” Besides maintaining a relentless touring schedule the band made their network television debut on The Jon Stewart Show and hosted MTV’s 120 Minutes. They also contributed a new version of “Where’d You Go?” to the movie Clueless. The band appeared in the film, performing the songs “Where’d You Go?” and “Someday I Suppose” during a party scene. The band was added to the main stage of the 1995 Lollapalooza tour. With the band on a roll Mercury re-packaged Question the Answers adding an EP titled Here We Go Again containing five additional tracks.
The BossToneS continued to tour, playing extensively throughout the U.S, Canada and Europe. In 1997 they began work on their next studio album. Released later that year, Let’s Face It would prove to be the band’s biggest seller, due largely to its first single “The Impression That I Get,” which reached number one on the Billboard Modern Rock chart. The album eventually went platinum. The album was followed by Video Stew, a VHS compilation of the band’s twelve music videos. The band appeared on Sesame Street’s Elmopalooza primetime television special where they performed the song “The Zig Zag Dance” with The Count. They also played Saturday Night Live, performing “The Impression That I Get.”
Capitalizing on the band’s popularity, Mercury released the album, Live From the Middle East in 1998. The album was recorded at the Middle East Nightclub in Cambridge Massachusetts during the band’s annual Hometown Throwdown series. The band continued to tour relentlessly. They did however find time to record a version of The Clash’s “Rudie Can’t Fail,” for the Burning London Clash tribute compilation. The song was produced by X bassist John Doe.
While on tour in Europe, Kevin Lenear quit the band and was replaced by Roman Fleysher. Fleysher had been recommended by producer and Stubborn All-Stars front man Jeff “King Django” Baker as a standout in New York City’s ska scene.
In 1998 Mercury Records’ parent company PolyGram was bought by Seagram and absorbed by the Universal Music Group, which Seagram also owned. Under the re-organization, Mercury was folded into the newly formed Island Def Jam Music Group. This was the third major regime change the Bosstones had endured during their time with the major label. In 2000, the band released the album Pay Attention on Island Def Jam. The album was again produced by Paul Q. Kolderie. The song “So Sad to Say” was released as a single and reached #22 on the Billboard rock charts. The album sold well and was a hit with their fans but ultimately did not sell as well as the previous release. The band, unhappy with the way the newly formed label had been handling them, asked to be released from their contract. Pay Attention was the last album for founding member Nate Albert, who departed in order to attend Brown University. Albert’s replacement on guitar was Lawrence Katz. Trombonist Dennis Brockenborough, also left the band shortly after Pay Attention was released. His replacement was former Spring Heeled Jack trombonist Chris Rhodes.