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Raekwon was born in Brooklyn, New York. He joined the Wu-Tang Clan in time to participate on Enter the Wu-Tang: 36 Chambers, the group's massively successful debut. He later signed a solo deal with Loud Records and, working with Ghostface Killah, released his first solo LP, Only Built 4 Cuban Linx... (originally to be titled Only Built 4 Cuban Linx... Niggaz), which debuted in 1995 to rave reviews, though the album's sales were sluggish. Only Built 4 Cuban Linx... is perhaps the most influential of all Wu-Tang solo projects, thanks to Raekwon's cinematic imagination and his creation of a narrative album format revolving around cocaine trafficking, criminal activity, and a rise through the ranks of the illegal industry. Albums to follow this thematic pattern, and to rely on the Cuban Linx' format for song construction, include Jay-Z's Reasonable Doubt, Nas's It Was Written, Notorious B.I.G.'s Life After Death, and even Raekwon's subsequent The Lex Diamond Story, which is organized around Mafia-based narrative progression, and first-person reporting on the drug trade. If the Genius is often described as the Wu's best overall lyricist then perhaps Raekwon is their best storyteller, and here he translates the epic themes and narratives of a Mafia movie into what critics consider a startlingly accomplished hip hop album.

Although Raekwon wasn't the first to make the connection between gangsta rap and the Cosa Nostra, his storytelling abilities on tracks such as Spot Rusherz led to many a comparison with Kool G Rap (who pioneered the idea), and the album as a whole is often credited for popularizing the trend of using Mafia and gangster movie motifs in rap music. Raekwon participated on Wu-Tang Forever with the rest of the group, and then released Immobilarity in 1999, to somewhat more mixed reviews than Only Built 4 Cuban Linx.... Many fans disliked his decision to use inexperienced, up-and-coming producers rather than the Wu-Tang's in-house producers, though the album went gold. Raekwon is also featured heavily on Ghostface Killah's albums Ironman and Supreme Clientele, as well as featuring on high-profile singles from Fat Joe ("John Blaze") and Outkast ("Skew It On The Bar-B"). He also appeared on the subsequent Wu-Tang Clan group albums The W (2000) and Iron Flag (2001).

His most recent album, The Lex Diamond Story, was released on December 13, 2003 on Universal Records, to mixed reviews (generally lukewarm critical reviews and wildly varying public reviews) and moderate success. His music video for the song "The Hood" featuring Tiffany Villarreal had few rotations on BET and nearly none on MTV. Raekwon has complained about this lack of promotion and vows that future releases won't suffer the same fate.[1] Raekwon's steady success has given him the chance to branch into business, become a Creative Officer of a major label and begin the creation of his own hip hop team, Ice Water Inc.