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65: Wyclef Jean

Wyclef Jean casts a big shadow in hip hop, R&B, and pop music. While The Fugees mega-hit "The Score" sold more records, his solo debut "The Carnival" is really what helped him cast that shadow. Some people have described it as a cold, calculated attempt by record execs to push urban music further into the mainstream. According to Wyclef, though, nobody knew if the record would even work!
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64: Joe and Dave Henry

Joe and Dave Henry, a folk singer and his screenwriter brother, ended up authoring the Richard Pryor biography "Furious Cool." At first glance, the connection makes no sense. Find out how it happened and why the brothers were obsessed with the legendary comedian.