There is more than one artist with the name Freeway: The first is: 1. Leslie Edward Pridgen (born March 24, 1977), better known by his stage name Freeway, is an American rapper. Freeway a.k.a. Philly Freeway began rapping while in high school. He later met fellow rapper Beanie Sigel, who would be signed to Roc-A-Fella and later help Freeway get a contract with the record label. Freeway became one of the label's most visible artists after making his first appearance on The Dynasty: Roc La Familia in 2000 and appearing on several other Roc releases before putting out his solo album..