Born in Croix-des-Bouquets, Haiti, Jean moved to Brooklyn when he was nine, then to New Jersey, where he began playing the guitar and studying jazz in high school. In 1987, Jean, his cousin Prakazrel Michel (Pras) and his classmate, Lauryn Hill, formed a group called the Tranzlator Crew before becoming The Fugees.
The Fugees signed to Ruffhouse Records and released their debut, Blunted on Reality, but the album was panned and sold poorly. Their eclectic follow-up, The Score, however, sold over six million copies and turned the trio into international stars. Jean soon announced plans to begin a solo career with 1997's Wyclef Jean Presents the Carnival Featuring the Refugee All-Stars (more typically called simply The Carnival). The album's guests included Hill and Pras along with Jean's siblings, the I Threes (back-up vocals for Bob Marley), Neville Brothers and Celia Cruz. The album was a major hit, as were two singles: "We Trying to Stay Alive" (adapted from The Bee Gees' "Stayin' Alive") and "Gone Till November" (recorded with the New York Philharmonic Orchestra).
Jean went on to work with artists including Santana, Tevin Campvell, Cypress Hill, Bounty Killer, Whitney Houston, Destiny's Child, Sublime, Simply Red, Mya, Sinéad O'Connor, Kimberly Scott, Mick Jagger, Canibus, The Black Eyed Peas and Eric Benet. The Fugees remained in limbo during this time, with the follow-up to The Score being continually postponed as all three members cultivated solo careers. Jean's second solo album was The Ecleftic: 2 Sides II a Book, recorded with guests Youssou N'Dour, Earth, Wind & Fire, Kenny Rogers, The Rock and Mary J. Blige. The critical reception was mixed, with many calling the album scattershot and too far-ranging to be cohesive.
Jean's third album, Masquerade, was released in 2002 and sold well, though critics frequently panned it.