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A hip-hop fixture since the dawn of the '90s, DJ Stretch Armstrong has been instrumental in presenting up-and-coming MCs through his media barrage of radio programs,
mixtapes, and even video games. The New York native's first notoriety came as one-half of the Stretch Armstrong and Bobbito Show, which quickly became one of the premier forums for the city's emerging hip-hop talent to be heard. Several of the '90s' biggest names in rap received early notice on the Columbia University radio program, including the debut of the Notorious B.I.G., or just Biggie Smalls as he was known in 1991. His appearance on the show was widely circulated, as were many of the show's legendary freestyle sessions, and led to Biggie's mention in a magazine column, which led to his introduction to Sean "Puffy" Combs. Biggie wasn't the only artist to freestyle on the show and subsequently blow up: Nas, Wu-Tang Clan, Mobb Deep, and countless others all appeared on the show. By 1998, the show had run its course, but not before the Village Voice declared the Stretch Armstrong and Bobbito Show "the best hip-hop show in New York" and Source magazine voted it "the best hip-hop show of all time." The demise of the show was not the end of Armstrong's radio career, however, and it was on Hot 97 -- the only commercial radio station in New York dedicated to hip-hop at the time -- that he continued with XL Radio.
The mid-'90s also saw the first of Armstrong's forays into record production with Dolo, which released singles from MF Grimm, the Korp, Dutchmin, and Powerule. Dolo was also the outlet for Stretch's Lesson mixtapes that always featured exclusive tracks and freestyles. Dolo was retired at the end of the '90s while Armstrong worked briefly with Game Records. The short association lasted long enough for the busy DJ to make it into over seven million homes as one of the radio personalities on Game Radio, one of the fictitious stations featured in the popular Grand Theft Auto III video game. Spit Inc., a new label helmed by the enterprising DJ, appeared in 2001 with a compilation featuring 50 Cent and Royce da 5'9"