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Raekwon joined the Wu-Tang Clan in time to participate on Enter the Wu-Tang (36 Chambers), the group's massively successful debut. Raekwon signed a solo deal with Loud Records and released his first solo LP, Only Built 4 Cuban Linx in 1995 to rave reviews, though the album's sales were sluggish. Working with Ghostface Killah, Raekwon's solo album is widely considered to be one of the masterpieces of rap in the 1990s and is still remembered by many fans as perhaps the greatest Wu-Tang solo LP thus far. His storytelling abilities on tracks such as Spot Rusherz led to many a comparison with Kool G. Rap , and the album as a whole is often credited for popularizing the use of 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 sold reasonably well. Raekwon also featured heavily on Ghostface Killah's albums Supreme Clientele and Bulletproof Wallets , as well as featuring on high-profile singles from Fat Joe (John Blaze) and Outkast {Skew It On The Bar-B).

His most recent album, The Lex Diamond Story , was released on December 13th, 2003, on the Universal Records label, to mixed reviews (generally lukewarm critical reviews and wildly varying public reviews) and moderate success. Raekwon's 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.