“I said, ‘Hey man, I’m not trying to squeeze you and I’m not trying to be disrespectful, but you know, you and Britney just broke up,’ ” he explained. “The other three, I think, were part of Justin Timberlake’s management team.” Back then, Hot 97 wasn’t too enthusiastic about playing Timberlake’s music, despite the soloist’s attempts to self-brand as an “R&B” singer instead of a pop star. “There were about five people in that room with us,” he told me recently, “and two of those people were representatives from Jive Records”-both Timberlake’s and Spears’ record label at the time. “Justin’s Low Blow May Send Britney Over the Edge,” read another.Ī decade later, Star still remembers how that interview played out behind the scenes. “Justin Timberlake Admits Oral Sex With Spears,” read one headline. “Oh man.” His inflection shifted, and he exclaimed, “OK, I did it!” Timberlake paused for a brief moment, letting out an awkward laugh. “Justin Timberlake is in the house, and I just want to ask you one question-did you fuck Britney Spears?” Troi “Star” Torain asked on air.
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