He was featured on Jay-Z's debut album, Reasonable Doubt, on the DJ Premier-produced "Bring It On", on In My Lifetime, Vol. 1, on the track "Face Off", and on Jay Z's third album, Vol. 2... Hard Knock Life, on the track "Reservoir Dogs" with The LOX and Beanie Sigel.
Gaither is credited as a co-writer for Puff Daddy's single "I'll Be Missing You".
He released his debut album, Middle Finger U, on Priority Records and EMI in 2000. The album featured two guest spots: one from Jay-Z ("Pregame") and another from Puff Daddy ("Do You See"); it also includes one track produced by DJ Premier. He released one single from this album, "For My Hustlaz". In 2004, he was featured on the single "Easy" from New Zealand DJ/producer P-Money's album Magic City. In 2006, he appeared at Jay Z's I Declare War concert to perform "Reservoir Dogs".

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