Emerging as a member of the Rhyme Syndicate, Everlast's first solo album Forever Everlasting (1990) – which was largely made possible by rapper Ice T – failed both critically and commercially. Following the album's flop, Everlast formed House of Pain with friends DJ Lethal and Danny Boy. Signed to Tommy Boy Records, the group's 1992 self-titled debut album went multi-platinum off the hit single "Jump Around". The group eventually disbanded in 1996, and Everlast once again pursued a solo career.
Everlast's second solo album Whitey Ford Sings the Blues (1998) – which was released a full eight years after his solo debut and after Everlast had a major heart attack – was both a commercial and critical success (selling more than 3 million copies). Whitey Ford Sings the Blues was hailed for its blend of rap with acoustic and electric guitars, developed by Everlast together with producers Dante Ross and John Gamble (aka SD50). The album's lead single "What It's Like" proved to be his most popular and successful song, although the follow up single, "Ends", also reached the rock top 10.
Despite the success of Whitey Ford Sings the Blues, Everlast's follow-up album, Eat at Whitey's (2000), failed commercially at first in the United States. However, it was eventually certified platinum. The album was also embraced critically, especially by Rolling Stone which reviewed the album between "good" and "great" and focused on it as that month's most important release.
In early 2006, Everlast teamed up with his former House of Pain mates DJ Lethal and Danny Boy to join the hip-hop group La Coka Nostra. The group first came to be due to the former House of Pain Hype man Danny Boy starting the group as a collective with rappers Slaine and Big Left (who has since left the group). Soon after the group started Ill Bill of a now disbanded Non Phixion and Everlast joined the group. Their first known song was "Fuck Tony Montana" which features B-Real of Cypress Hill and Sick Jacken. Due to the popularity of the song online, the group released several more online for free.
The group's debut album A Brand You Can Trust was released on July 14. The album features guests like Snoop Dogg, B-Real, Bun B, Immortal Technique, Sick Jacken and Q-Unique. La Coka Nostra then joined the likes of Nas and Ill Bill's brother Necro on Rock The Bells. Everlast left the group in 2012 due to his daughter's medical issues.