Fortified by his undeniable musical talent-and make no mistake, he is one of the greatest performers of recent history-Timberlake’s boy-next-door identity endured for decades, even in the face of evidence that contradicted it. It’s a searing reminder of the part he played in the performance, its fallout, and the media’s continued scrutiny of female artists whose sexuality was inextricable from their image. Twenty years later, in a drastically changed cultural landscape, 2000s-era Justin Timberlake looks a lot different.īetween Britney and Janet, Justin once skated through controversies that had grievous PR effects on the women around him. The conversation is likely to continue: The Times is releasing a new documentary on Friday, this time focused on Timberlake’s infamous Super Bowl incident with Janet Jackson. Then Justin gave him a quote to shock the tabloid world. “I said, ‘Hey man, I’ll play it four times a day.’ Then I said, ‘Goddamn it, I’ll play this record five times a day, Justin, what do you think?’ ” They were just joking around, Star said. “He didn’t really want to talk about it, but I was like, ‘Look, I’ll play this goddamn song of yours, I swear to you, two times a day for two weeks if you could just give me some information here.’ ” Timberlake “kind of smiled, he almost turned beet red,” Star said. “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.