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Although his status within Boston's rap underground is legendary, hardcore underground rapper Big Shug is widely known for his long-time affiliation with hip-hop duo Gang Starr and its producer-half, DJ Premier. Deemed top general of the Gang Starr Foundation collective, Big Shug's unrelenting flow and predisposition for menacing rhymes — personified by his massive and imposing physique — were best captured in his classic verses on Gang Starr cuts "F.A.L.A" (from 1994's Hard to Earn) and "The Militia" (from 1998's Moment of Truth). Born Cary Guy, the hardcore rapper spent much of his early life in Boston's Mattapan (known locally as "Murdapan") section. Because his mother abandoned his family and his father grappled with alcoholism, Guy had to fend for himself on the streets. The friendship that he eventually made with Gang Starr's MC, Guru, is actually where the origins of Gang Starr lie. Shug stimulated Guru's interest to rhyme in somewhat of a mentoring capacity. However, too embedded in Boston's underbelly of violence and drugs, Shug wound up incarcerated, and Guru moved to New York, taking the Gang Starr name to form one of hip-hop's most innovative groups with DJ Premier. When Shug was let out, he was very inspired by Gang Starr's success. Guru and Premier showed their respects by including him on each of their albums, beginning with Hard to Earn in 1994. Throughout the '90s, Shug recorded a few DJ Premier-produced 12"s for Payday and Chrysalis, but his first full-length record, Who's Hard (2005), didn't appear until well over a decade of being a seasoned veteran. Actually, many of the album's tracks were some of those ten-year-old recordings. In 2007, he signed onto indie rap powerhouse Babygrande to release his follow-up effort, Streetchamp. Unlike the previous album, Shug only took a few beats from DJ Premier, handing most of the production work over to Canadian up-and-comer MoSS.