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Born in Boston, Massachusetts, Guy spent much of his early life in Boston's Mattapan area (known locally as "Murdapan"). Growing up, he forged a friendship with future Gang Starr MC, Guru.The two were separated when Shug was imprisoned and Guru moved to New York, forming Gang Starr with DJ Premier. On his release, Shug again hooked up with Guru, joined the Gang Starr Foundation, and contributed to each of Gang Starr's albums, beginning with Hard to Earn in 1994 (on "F.A.L.A."). He also appeared on "The Militia" from 1998's Moment of Truth, and contributed to Guru's "Jazzmatazz" albums During the 1990s, Shug recorded a few 12-inch singles produced by DJ Premier for Payday and Chrysalis, but his first proper solo album, Who's Hard was not released until 2005 and half of the songs were handled by DJ Premier. He signed to New York's Babygrande in 2007, and released his second album, Streetchamp. The album was produced by MoSS and DJ Premier and features guest appearances from DJ Premier and Sean Price. A third solo album, Otherside of the Game, was released in November 2008, and features DJ Premier, Bumpy Knuckles, Billy Danze of M.O.P., Termanology, Blaq Poet, and Singapore Kane. He performed at the 2009 Boston hemp fest. He is featured on the single "Tap Out", which appears on M-Dot & DJ Jean Maron's 2010 album Run MPC. In 2010 he also collaborated with (artist) Aztech and (producer) Reel Drama on their album Hybrid Genetics. In 2010 he collaborated with west coast hip hop artist Spinz on a song called "Round Tha World" that was recorded while touring Europe.