Jean was born in Croix-des-Bouquets, Haiti. In 1982, he immigrated with his family as a thirteen-year-old boy to the United States; after living in Brooklyn, New York, they settled in East Orange and Newark, New Jersey. He began to make music as a child and has cited reggae artist Bigga Haitian as one of his early influences, as well as neighborhood heroes MC Tiger Paw Raw and producer Lobster v. Crab. His mother recognized his musical talent and bought him a guitar when he was in his teens; he played music to earn respect.

Jean announced plans to begin a solo career with 1997's Wyclef Jean Presents the Carnival Featuring the Refugee All-Stars (generally called The Carnival). The album's guests included Lauryn Hill and Pras along with Jean's siblings' group Melky Sedeck; the I Threes (back-up vocals for Bob Marley); The Neville Brothers and Celia Cruz. The album was a 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).  Released in 2000, Jean's second solo album The Ecleftic: 2 Sides II a Book was recorded with guests including Youssou N'Dour; Earth, Wind & Fire; Kenny Rogers; The Rock; and Mary J. Blige. With Blige he released "911" as a single. He was nominated for Best Hip-Hop Act at the 2000 MTV Europe Music Awards.  Following the terrorist attacks of September 11, 2001, Jean participated in the benefit concert America: A Tribute to Heroes contributing a cover of the Bob Marley song "Redemption Song". His third album, Masquerade, was released in 2002. His fourth album, The Preacher's Son, was released in November 2003 as the follow-up to his first solo album, The Carnival. In 2004, he released his fifth album, Sak Pase Presents: Welcome to Haiti (Creole 101) (released in the United States by Koch Records). Most of its songs are in his native language of Haitian Creole like "Fanm Kreyol" with the French Caribbean Admiral T. He also figured on the album Mozaik Kreyol of this one in the song "Secret Lover". Then he covered Creedence Clearwater Revival's song "Fortunate Son" for the soundtrack of the 2004 film remake of The Manchurian Candidate and wrote the song "Million Voices" for the film Hotel Rwanda.  Jean also produced and wrote songs for the soundtrack to Jonathan Demme's 2003 documentary The Agronomist, about the Haitian activist and radio personality Jean Dominique. With Jerry 'Wonder' Duplessis, Jean also composed the score of the documentary Ghosts of Cite Soleil, He helped produce the film and he appears briefly onscreen speaking by telephone in 2004 to a "chimere" gang-leader and aspiring rapper, Winston "2Pac" Jean.

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