After Erick Sermon of the seminal group EPMD spotted Redman freestyling in a New York club, Sermon added him to the Hit Squad crew of aspiring MCs (along with K-Solo, Sermon's EPMD, Das EFX and Keith Murray). Redman made his rapping debut on the EPMD songs "Hardcore" and "Brothers On My Jock" off their third album Business As Usual (Def Jam 1990). Redman's 1992 Def Jam debut Whut? Thee Album broke into the US Top 50, achieved gold status in the United States. Prominent hip hop magazine The Source subsequently named Redman the Rap Artist of the Year for 1993.
Redman's solo career continued throughout the remainder of the decade, with each of his albums selling at least half a million copies. His musical style has remained very consistent, rarely deviating from a combination of Redman's unique braggadocious wit and hard, P-funk-influenced beats. In addition to releasing albums under his own name, he is part of the group Def Squad (along with Keith Murray and Erick Sermon) with whom he released the 1998 album El Niño, and also has formed a close partnership with labelmate Method Man (of the Wu-Tang Clan) with whom he released the 1999 album Blackout!. He has also collaborated extensively, both with hip hop artists and with artists from other genres; the long list of artists and groups he has worked with includes Wyclef Jean, Snoop Dogg, Scarface, The Offspring, Eminem, Gorillaz, D'Angelo, Me'shell Ndegeocello, 2Pac, Jodeci, Cypress Hill, The Oak Ridge Boys, De La Soul, Tribe Called Quest, KRS-One, Beverley Knight, IAM and Christina Aguilera. Redman had his best-known international mainstream hit with Aguilera, when he featured on her 2002 single "Dirrty". Another surprising collaboration, which was unable to garner the same support as "Dirrty", was the 2005 underground hit "I Still Need You" featuring the vocal stylings of Conway Twitty. Since the release of Redman's last studio album he has kept his fans happy by independently releasing the Ill At Will mix tapes which feature various members of his Gilla House crew, including Saukrates & Icarus.
Redman is scheduled to release a new album in March 2007 titled Red Gone Wild.