On Sept. 23, 2002, a newly single, 21-year-old Justin Timberlake sat down for a radio interview. It wasn’t routine: He was set to appear on The Star & Buc Wild Morning Show, on the most influential hip-hop station in the country, Hot 97. At the time, hosts Star and Buc Wild were the ultimate tastemakers. Their radio show was famous for irreverently grilling celebrities like A Tribe Called Quest, Busta Rhymes, and Nas. They’d established a wide fan base for their fearless, blunt interviewing style. Timberlake, meanwhile, had recently split from both his boy band, *NSYNC, and his girlfriend, Britney Spears. A week before, he’d debuted his solo single “Like I Love You,” featuring Clipse. His chaste public persona was in the midst of a major revision.
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