Emerging as a member of the Rhyme Syndicate, Everlast's first solo album Forever Everlasting (1990), largely made possible by MC Ice-T, was a disappointment commercially. Following the album's failure, Everlast teamed up with DJ Lethal and high school friend Danny Boy to form House of Pain in Los Angeles, CA. Including Ice-T, they all attended Taft High School. The group was signed to Tommy Boy Records, and their eponymous debut album (1992) went multi-platinum, spawning the successful DJ Muggs produced single "Jump Around". This song was also remixed twice by Pete Rock, one version featuring a verse from him and one without. The album also featured Cypress Hill member, B-Real, on the song "Put Your Head Out".

Fashioning themselves as rowdy Irish American hooligans (Lethal is actually of Latvian heritage), they toured with various rap and alternative-rock bands such as The RamonesBeastie Boysand Rage Against the Machine after their breakthrough. They participated together with Helmet, along with several other rap acts, on the influential 1993 rock-rap collaborative Judgment Nightmovie soundtrack (Everlast also played a villain in the film). The group eventually disbanded in 1996, and Everlast once again pursued a solo career.