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Pretty Willie broke into the major-label rap game in the wake of fellow St. Louis rapper Nelly's phenomenal success. Though the city had a fertile rap scene long before Nelly became an overnight success in summer 2000, fellow St. Louis artists such as Pretty Willie never had a shot at major-label success. However, in 2002 -- a year or so after, first, Nelly's breakthrough and, in turn, the similar success of Nelly's St. Lunatics posse -- Universal unsurprisingly introduced the masses to Pretty Willie, another St. Louis rapper with cute looks and a singsong-y pop-rap style, both much like Nelly. And, again unsurprisingly, Pretty Willie's debut single, "Roll Wit Me," bared more than a coincidental resemblance to Nelly's popular hit from a year earlier, "Ride Wit Me." However, unlike Nelly, Pretty Willie struggled to scale the charts. ~ Jason Birchmeier, All Music Guide
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