Early Career
Born Leslie Pridgen, Freeway began his career by participating in freestyle battles in his high school and met fellow Philadelphia native Beanie Sigel while rapping on stage at a hometown nightclub. Not long after being signed to Roc-A-Fella Records, Sigel put in a word for Freeway, who made his first appearance on The Dynasty: Roc La Familia, on the track "1-900-Hustler" with Beanie, Jay-Z, and Memphis Bleek. After the appearance, Jay-Z signed him to a deal; he was featured on "Think it's a Game," also alongside Jay-Z, on Beanie's second album The Reason. In 2001, he underwent a notorious freestyle battle with then-unsigned rapper Cassidy, hosted by Swizz Beatz and lost with a unanimous judges decision.
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