He has spent the majority of his career affiliated with the Wu-Tang Clan, frequently collaborating with Method Man and Ghostface Killah.

[7][8] After 1996's The Lost Generation, Shyheim's career saw a string of underperforming releases over the next eighteen years, and was finally derailed due to a hit-and-run conviction.

[12] He also shared the stage with the Notorious B.I.G., Tupac Shakur, Scoob and Big Daddy Kane at Madison Square Garden, for a live freestyle session.

[6][9] He also made an appearance on Big Daddy Kane's "Show & Prove," which featured Ol' Dirty Bastard, Sauce Money, Scoob and Jay-Z.

[10] He has had roles in films such as the 1996 Pam Grier, Fred Williamson, Jim Brown, and Richard Roundtree vehicle Original Gangstas,[13][failed verification][14] In Too Deep,[15][10] and The Preacher's Wife[9][10] and he also starred in the television show The Parent Hood.