How Justin Timberlake Came Undone

On Sept. 23, 2002, a newly individual, 21-year-old Justin Timberlake sat down for a radio consultation. It wasn ’ metric ton routine : He was set to appear on The Star & Buc Wild Morning Show, on the most influential hip-hop place in the state, Hot 97. At the time, hosts Star and Buc Wild were the ultimate tastemakers. Their radio indicate was celebrated for irreverently grilling celebrities like A Tribe Called Quest, Busta Rhymes, and Nas. They ’ five hundred established a wide fan base for their audacious, blunt interviewing style. Timberlake, meanwhile, had recently split from both his boy band, *NSYNC, and his girlfriend, Britney Spears. A workweek earlier, he ’ five hundred debuted his alone one “ Like I Love You, ” featuring Clipse. His chaste public persona was in the midst of a major revision .
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“ Justin Timberlake is in the theater, and I fair want to ask you one question—did you fuck Britney Spears ? ” Troi “ Star ” Torain asked on air. “ Yes or no ? Come on, man. ”

Timberlake paused for a brief moment, letting out an awkward laugh. “ Oh man. ” His prosody shifted, and he exclaimed, “ OK, I did it ! ”
“ Justin Timberlake Admits Oral Sex With Spears, ” read one headline. “ Justin ’ s Low Blow May Send Britney Over the Edge, ” read another.
A decade late, Star still remembers how that interview played out behind the scenes. “ There were approximately five people in that board with us, ” he told me recently, “ and two of those people were representatives from swing Records ” —both Timberlake ’ randomness and Spears ’ record label at the time. “ The other three, I think, were separate of Justin Timberlake ’ s management team. ” Back then, Hot 97 wasn ’ t besides enthusiastic about playing Timberlake ’ randomness music, despite the soloist ’ sulfur attempts to self-brand as an “ R & B ” singer alternatively of a pop ace. But Star liked him. “ I said, ‘ Hey man, I ’ m not trying to squeeze you and I ’ m not trying to be aweless, but you know, you and Britney precisely broke up, ’ ” he explained. “ He didn ’ t very want to talk about it, but I was like, ‘ Look, I ’ ll play this goddam song of yours, I swear to you, two times a sidereal day for two weeks if you could just give me some information here. ’ ” Timberlake “ kind of smile, he about turned beet crimson, ” Star said. “ 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 sidereal day, Justin, what do you think ? ’ ” They were just joking about, Star said. then Justin gave him a quote to shock the yellow journalism world.
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They were just joking around, Star said. Then Justin gave him a quote to shock the tabloid

 

world.

Publicly, 2002 Timberlake was the sensitive ex–boy bander, a brokenhearted heartthrob excessively civilized to speak ill of his ex-wife but grok adequate to burn her in his songs ( without naming her, of run ). simultaneously, there were rumors that he privately said things like “ Dude, smell my fingers ” to choreographers to brag about having sex with America ’ mho impossible sweetheart : objectified and infantile, the bang-able pure virgo next door. When Justin admitted to having sex with Britney, it was a significant botch to Spears ’ brand ; at the meter, she had told the press she wanted to try to remain celibate until marriage. But only recently has Timberlake ’ south reputation been affected by the way he acted and spoke back then, due in no small region to the popularity of the New York Times film Framing Britney Spears .
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The conversation is probably to continue : The Times is releasing a newfangled documentary on Friday, this time focused on Timberlake ’ s ill-famed Super Bowl incident with Janet Jackson. It ’ s a searing reminder of the separate he played in the performance, its side effect, and the media ’ s continued examination of female artists whose sex was inextricable from their effigy. Twenty years subsequently, in a drastically changed cultural landscape, 2000s-era Justin Timberlake looks a draw different .
Between Britney and Janet, Justin once skated through controversies that had dangerous PR effects on the women around him. Fortified by his undeniable musical talent—and make no mistake, he is one of the greatest performers of late history—Timberlake ’ sulfur boy-next-door identity endured for decades, even in the face of testify that contradicted it. The new reckoning around him feels like a cultural exorcism, a gamble to use the son band vessel to purge ourselves of the evils he now represents to many. But behind the scenes, he was at once a cagey self-marketer and a blank, withholding presence at the hub of conflict, surrounded by publicists and media and managers who were crafting his visualize, besides. Timberlake has become the perfect emblem of a bygone era that rewarded guys precisely like him—until it didn ’ deoxythymidine monophosphate .
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Justin Timberlake was once the center of the population, if you can remember far back enough : At the turn of the millennium, when fear of an unknown future could be pacified by the sugary-sweet five-part harmonies of Y2K boy bands, Timberlake was it. The acme. *NSYNC ’ mho rising ace. An all-American, good-ol ’ mama ’ s boy with a warmly lyric tenor from Shelby Forest, Tennessee, Timberlake was blessed with a harmonious face and thick curls hoisted to the gods and given the appearance of ramen .
He was born in 1981. His stepfather, Paul Harless, was a Baptist church choir conductor, and his mother, Lynn Harless, was soon to become one of the greatest stage parents in american pop music history. ( Justin ’ s biological beget, Randy Timberlake, whom Lynn referred to as the “ sperm donor ” in a 2006 Rolling Stone cover report, played bass and sing eminent harmonies in a bluegrass band. She credits him for her son ’ sulfur virtuosity. ) By 12, Timberlake was selected to star in Disney ’ s All-New Mickey Mouse Club. For two seasons, he was a star. At 13, the show was canceled, and the following year, *NSYNC ’ s Chris Kirkpatrick called Timberlake ’ s ma about a fresh vocal group. With a co-sign from the Disney Channel, *NSYNC became massive : 2000 ’ s No Strings Attached sold more than 1.1 million copies in its foremost day and more than 2.4 million in its first workweek, setting a global record they held for 15 years. And Justin was their leader .
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He was besides a child when he entered the entertainment industry, and he was exploited by it : by coach Lou Pearlman, who had him and the other boys sign what litigant Helene Freeman labeled “ the worst contract in music history, ” according to mate band extremity Lance Bass ’ memoir, earning pennies on the dollar for the arduous hours worked. In 2006, Timberlake told Rolling Stone he felt the band “ was being monetarily raped by a Svengali. ” The future class, a landmark Vanity Fair article alleged that Pearlman had been far more than financially exploitative ; he had sexually assaulted multiple boys whose careers he made. ( Unlike the early members of *NSYNC, like Lance Bass, who released a documentary on Pearlman ’ s fiscal exploits in 2019, The Boy Band Con : The Lou Pearlman Story, Justin Timberlake has rarely spoken about the coach. )
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It is besides key to remember that as a intersection of the child-star system, Justin most probable grew up with media training in adolescence that meant internalizing publicity strategies intended to help him maintain relevance—such as staying lull and listening to the professionals. Silence meant that his noteworthy endowment could speak for itself. It besides meant that his populace character would come across as wholly neutral, available to everyone .
John Norris, a former MTV VJ, remembers that his earliest interviews with Timberlake were during the 1999 *NSYNC tour, where Britney Spears was an opening dissemble. Compared with the “ fraternity boy ” vibraphone of some of the other band members, Timberlake seemed less goofy, more self-conscious. At one point, Timberlake took Norris for a drive in his fresh car. Hanging from his rearview mirror were the letters “ WWJD. ” “ I ’ m such a heathen and know so little about being a good Christian boy that I knew nothing about the expression, ‘ What would Jesus do, ’ ” Norris recalled. “ so, I was like, ‘ What is that thing hanging there ? ’ And Justin downplayed it, ‘ Oh, it ’ randomness equitable a thing for, like, checking yourself. ’ And I ’ m like, ‘ What do you mean ? Does it stand for something ? ’ He didn ’ thyroxine want to go into it. ” JT had the foresight not to make an explicitly religious argument ; from a new age, he was “ reasonably decisively anti-political, ” said Norris, and “ singularly uninterested in getting excessively divisive. ” ( Timberlake ’ s representatives did not respond to multiple requests for gloss. )
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In the early 2000s, this was what the culture demanded of mega pop stars. apolitical palaver that, more frequently than not, veered conservative, the kind of post-9/11 patriotism that pretended not to take a side. Think Jessica Simpson, Christina Aguilera, and the adjacent generation of Disney Channel starlets like Hilary Duff. If and when controversy arose—like in 2003, when Madonna and Spears shared a kiss at MTV ’ s Video Music Awards, with a television camera trained on Timberlake in the audience—it was more much than not craftily staged. It was curated controversy, obsequious to the consultation, orchestrated without requiring that stars take a particular ideological stand. ( Consider the alternate : When Natalie Maines of the Dixie Chicks told a push in London that her group was “ ashamed the president of the United States is from Texas ” in gain of the U.S. invasion of Iraq, the group was blacklisted from radio, kneecapping the Dixie Chicks ’ careers. People organized certificate of deposit burnings in protest. )
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Back when fear of an unknown future could be pacified by the sugary-sweet five-part harmonies of

Y2K

boy bands, Timberlake was it. The

 

pinnacle.

During that era, the relationship between celebrities, paparazzo, and yellow journalism media was besides peculiarly symbiotic and toxic. The supermarket magazine industry—not yet amply pummeled by the internet ( TMZ, Just Jared, and PerezHilton.com didn ’ metric ton appear until the mid-2000s ) —was viciously competitive. Magazines like Us Weekly and People and Star were obsessed with obtaining exclusives, which required constant negotiation with celebrities and their publicists. And stars, in turn, were besides dependent on tabloids to shape their own narratives .
After *NSYNC called it quits in 2002—largely because JT wanted to pursue a Michael Jackson–esque career—he released “ Like I Love You, ” from his then-forthcoming album Justified, recorded with the Neptunes and Timbaland, the identical same track Star promised to blast multiple times a day on Hot 97. today, many have argued that JT rose to solo fame on the shoulders of Black talent without in full giving them their ascribable. Janet Jackson was featured on a late album cut, “ ( And She Said ) Take Me now, ” merely a few years before the ill-famed Super Bowl .
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“ Like I Love You ” hit No. 11 on the Billboard Hot 100, an impressive benchmark for any performer, but not adequate of a spatter for him as a soloist, considering the sum ubiquity of his group. It besides arrived with a new, carefully cultivated picture : Justin Timberlake was now the inoffensive everyman with some sting, done faulty by his punic ex-girlfriend .
It stands to argue that JT ’ second team recognized his dissolution with Britney Spears made for some incredible publicity. If he couldn ’ thyroxine crack the exceed 10 on his own, possibly the narrative of America ’ s darling ability couple calling it quits, with JT as the tender-guy victim, would do the trick. According to tabloid sources from that era, Timberlake on his own was not a huge string for readers. “ He ’ s a pretty closed book. We always had worry generating a fortune of interest, and the interest was constantly in relation to whoever he was dating, ” one former celebrity magazine editor from the 2000s told Slate. But the Britney dissolution was a rare moment when Timberlake and his people played ball with the urge. “ I think we had five minutes with him and a photographer that he knew. ” The yellow journalism editor recalled that they ’ five hundred hear “ Britney was sleeping with dancers or something like that, ” but suggested “ that was clearly his people getting in front of that narrative and being proactive. ” ( Rumors of infidelity have never been confirmed, though they continue to crop up. )
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Justin in a white turtleneck sweater and Britney in a low-cut black top lean toward each other while seated in the audience.
“ The hale thing was a post-breakup cooperative, ” he continued. “ And we were telling the report that Britney cheated on him. That was the whole setup. ” Given the at hand dismissal of Timberlake ’ s newfangled grief album, the tabloid editor program believed that “ it was all very choreographed to be a retaliation floor. ”
That new album was anchored by Justin ’ s first base solo hit, “ Cry Me a River ” —a not-so-thinly-veiled criticism of Britney, starring a video-actor lookalike. ( “ You don ’ t have to say what you did/ I already know, I found out from him, ” he sang. “ You told me you love me/ Why did you leave me all alone ? ” )
It cemented his identity as a deep-feeling solo artist. His sound recalled a ashen neo-soul Usher, indebted heavily to the Neptunes and Timbaland ’ s production, and his ethos was aphrodisiac, single, lawsuit and tie–toting bachelor. He claims he wrote “ Cry Me a River ” in two hours. The message worked : celebrity media tended to side with “ Team Justin, ” with headlines like “ alone in every way, the aphrodisiac singer sets the record straight. ” ( There might be no better representation of the twist cultural mores of the time than a 2002 Details cover wrinkle : “ Can we always forgive Justin Timberlake for all that effeminate music ? Hey … at least he got into Britney ’ s pants. ” ) meanwhile, Britney headlines trumpeted : “ Did she betray him ? ”, “ Britney cracks up ! ”, and “ Boozing Britney out of see. ” As a leave, her own interviews became wrong control condition : no, she doesn ’ t do drugs. She likes red wine but never drinks in overindulgence. She ’ randomness still the same girl we constantly knew her to be .
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What frequently goes unmentioned about Justin ’ s kinship with ’ 00s yellow journalism polish is that he wasn ’ t actually very concerted with the magazines that supported him. “ Justin actually despised paparazzo. Didn ’ deoxythymidine monophosphate manage about them one act, ” said Danny Ramos, a former paparazzo. “ I couldn ’ thyroxine go up to him like, ‘ Hey Justin, how you doing ? ’ He ’ sulfur probably going to have me in a headlock .
“ You get Justin Timberlake and a paparazzo together, and it ’ sulfur explosion, ” Ramos said. “ It ’ s not going to go down good. ”
If it sounds aggressive, that ’ mho because it was. There are videos of Justin in the mid-2000s, peculiarly around the time he dated actor Cameron Diaz ( aka, a year after he broke things off with Britney ), where he is seen smacking paparazzo cameras out of the hands of videographers. These are violent, protective gestures that would ’ ve made memorable front-page newsworthiness if it were Britney doing the attack— and of course, they did —like when she smitten Ramos ’ hand truck with an umbrella .
“ There are a lot of celebrities ” — “ like Paris, or Lindsay, or Britney, ” Ramos said— “ I call it ‘ teasing. ’ One infinitesimal they want it, the adjacent minute they don ’ t. And thus, with Justin, it wasn ’ t like that at all. Justin was like, ‘ Get that shit away from me. ’ ” It was inherently gendered—Britney, Paris, and Lindsay were ineffective to change their minds about paparazzo ; Justin was respected for his indignation. And that says nothing about the imperativeness they must ’ ve feel, as young women, to play courteous with the camera men who knew where they lived and followed them daily .

“The whole thing was a post-breakup cooperative,” one tabloid editor told Slate. “And we were telling the story that Britney cheated on him. That was the whole

 

setup.”

Ramos, for his separate, has started reckoning with this dynamic immediately in a room he says he didn ’ thymine back then. “ It [ was ] a double standard, ” he told me. “ At that time, you could say it was like male chauvinism. It was, front, ‘ Let ’ s just cream on the girls. ’ It was like being bullied. And the guys were not picked on american samoa much as the females. ”
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The mainstream media jumped on the dissolution narrative Timberlake ’ s team was pushing, besides. In an ill-famed interview with Barbara Walters on ABC News ’ 20/20 conducted in 2002, Justin offered a cabalistic but kind explanation for his dissolution with Britney : “ We ’ ra not perfective. I don ’ thyroxine estimate anybody. ” then he performed an unreleased track. “ Frankly, baby, you ain ’ metric ton worth the accelerator in my BMW, ” he sang. “ But to look at it positively/ At least you gave me another sung about a atrocious woman/ And that ’ s you. ” Once again, he was a valet scorned ; Britney was unfaithful and barbarous. When Walters asked Justin if he and Britney kept her pledge to wait to have sex until marriage, he laughed and said, “ Sure. ” Walters responded with a chuckle, “ All correctly. I asked it, you answered, right ? We both did our job. ” ( “ I ’ ve merely slept with one person my hale biography, two years into my relationship with Justin. I thought he was the one. But I was improper. I didn ’ deoxythymidine monophosphate think he was gon sodium go on Barbara Walters and sell me out, ” Britney told W magazine in 2003. “ The most irritating thing I ’ ve always experienced was that dissolution. ” )
Britney wasn ’ t the only one who suffered the repercussions of JT ’ south media promotion. When Timberlake grabbed Janet Jackson ’ s chest at the 2004 Super Bowl halftime show—a stunt that was supposed to reveal bolshevik fabric and incidentally revealed her breast instead—he was able to return to the limelight unharmed. immediately following the performance, Justin told Access Hollywood, “ Hey, man, we love giving y ’ all something to talk about. ” A week later, Janet was barred from the Grammys, and her career has never in full recovered. Justin, meanwhile, performed and won the award for Best Male Pop Vocal Performance. even recently, as the Times announced it will turn its attention to this incidental in its objective, headlines referred to it as the “ Janet Jackson Super Bowl Scandal. ”
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Justin stands beside Janet holding a microphone.
Over the adjacent few years, his star continued rising. In 2006, on his alone read following the Super Bowl, FutureSex/LoveSounds, Timberlake basically rewrote “ Cry Me a River ” in “ What Goes Around … Comes Around. ” ( “ If he hasn ’ deoxythymidine monophosphate however invented a persona intriguing adequate to live up to his music, give him credit for being one of the few white men hush brave enough to make Black music, ” wrote one critic. “ These songs update the early-eighties Minneapolis sound : tense drum machines, high-pitched synth squiggles, and staccato flinch bass lines. ” Beneath the sarcasm of that recapitulation, Justin was celebrated for good songs developed out of an infatuation with Black music. ) The songs were masterfully crafted, a lesson in how to grow up post–teen pop superstardom. Their message was besides a kind of self-victimization disguised as grief. ( “ All of these things people told me/ Keep mess with my head/ Should ’ ve picked honesty/ then you may not have blown it, ” he sang in “ Cry Me a River. ” ) The same could be said about his a-list act roles that followed—Sean Parker in 2010 ’ s The Social Network, Dylan Harper in 2011 ’ s Friends With Benefits, hell, his beloved Saturday Night Live cartoon, “ Dick in a Box ” —allowed Justin to have it both ways : work caddish and do an act sending up what it is to be a computer-aided design .
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It wasn ’ t until about a decade late, with 2018 ’ s critically panned Man of the Woods, that Timberlake ’ south fortunate son condition began to fade. JT ’ sulfur 2013 neo-soul albums, The 20/20 experience and The 20/20 Experience–2 of 2, were acclaimed for their consistency—glossy pop by a sensible and sexy bon vivant. When he reappeared a few years belated after a musical hiatus, gone were the Armani suits ; rather, 2018 Justin played with folk music music iconography, writing his own gospel without any bizarre elasticity, like a man in repentance. He seemed much more self-reflective in his art, and vague—the age american icon leaning into Americana, attempting to come across as the mature family man alternatively of the brassy, heartbroken-yet-suave bachelor he had been for so many years. Publicly, it looked a draw like a retreat into whiten —Western, Manifest Destiny–inflected sounds that celebrated the fabulous masculinity of the great outdoors, flannel shirts and all, despite the fact that JT continued to work with producers Timbaland and the Neptunes on the project. The R & B was turned down, and then was the fun .
By 2018, cultural appropriation had permeated mainstream sermon. From an external perspective, Man of the Woods seemed designed in part to signal understand of the stream moment. But the album was a disappointment. Justin was known for excessive pop records and epic stadium shows, then when he stripped it back, he lost mainstream applaud. ( loyal listeners, at least, were endeared to his back-home familism. JT ’ s son ’ south name, Silas, means “ man of the woods ” in Latin. ) On one of the record ’ s better cuts, “ Say Something, ” with Chris Stapleton, they sing on the bridge, “ Sometimes the greatest way to say something is to say nothing at all. ” Part of Justin ’ s charm was constantly his cheerfulness, but on record, now, it lacked charisma.
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In the years that followed, Justin Timberlake ’ s pop-star persona floundered. Media coverage shifted from glowing reviews to takedowns of his self-indulgent records. The cultural world around him evolved, excessively. In 2018, he signed up to work on Woody Allen ’ second movie Wonder Wheel, telling the Hollywood Reporter he chose “ not to get into ” Allen ’ s pedophilia allegations. That same year, when cultural conversation was dominated by the # MeToo motion, Justin Timberlake wore a Time ’ s Up pin to the 2018 Golden Globes, despite working with Allen. He shared a selfie wearing the peg, smiling with his wife, Jessica Biel, and then captioned it—really— “ DAMN, my wife is hot ! # TIMESUP. ”
In 2019, a paparazzo captured him holding hands with co-star Alisha Wainwright from the movie Palmer during a night out, and many-sided cheating rumors continued to swirl around him. So he issued a bumbling statement that was addressed to his “ wife and syndicate ” but clearly mean as public damage command, apologizing for putting them through “ an embarrass situation ” while insisting that he hadn ’ t cheated with his co-star. then came 2021 and Framing Britney Spears. In the movie, Timberlake ’ s interview with Diane Sawyer was put on broad display, inspiring new on-line ardor against him. And so this prison term he issued a broad apology to all the women he ’ d—wittingly or unwittingly—hurt. “ I have not been perfect in navigating all of this throughout my career, ” he wrote on Instagram. He said that he ’ five hundred “ benefited from a system that condones misogyny and racism, and wrote, “ I know this apology is a first step and doesn ’ t absolve the past. ”
Timberlake had clearly come to a realization : His once marketable silence nobelium longer flies. But his apologies felt to many like a belated, excavate attempt to take a stand after decades of bookish disinterest. “ I think that the start zeitgeist, what we want from pop in 2021, or what real pop fans want from male pop artists is sol unlike from what Justin Timberlake was : unalterably male, unalterably straight, ” said Norris, the erstwhile MTV VJ. “ I think there are qualities we celebrate now that were not even possible for a male dad artist in the early 2000s. ” It was not “ part of Justin ’ s makeup. I mean, he golfs, for sleep together ’ south sake. Right ? That ’ s it in a nutshell. Does Harry Styles golf ? I don ’ thyroxine think so. ” ( He does, but the point stands. ) today, Timberlake writes songs for children ( “ Can ’ t Stop the Feeling ! ” ), voices cartoons ( Trolls ), and stars in under-the-radar roles that validate his perennial soft-guy identity ( Palmer ) .
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But his elapse from the function of cultural darling is barely a professional death. Timberlake was merely given an opportunity that Britney Spears and Janet Jackson never got : to ease gently out of the foreground, to step into the background but not to suffer because of it. He never faced the same harassment from paparazzo or the press that the women around him did, and his career has never in truth stalled. He performed at Joe Biden ’ s inauguration ceremony in January and has besides been back in the studio—writing the flaccid feel-good sung “ Better Days ” with singer-songwriter Ant Clemons. Hell, Trolls World Tour broke digital box office records and made $ 100 million in rentals alone survive year. In January, Timberlake appeared on his good friend Jimmy Fallon ’ s Tonight Show, teasing new music. Since then, he ’ mho been lying low amid comeback album rumors, waiting patiently, it seems, for his opportunity to reemerge. After all, Timberlake is a aim chameleon—ready to shapeshift to suit what he thinks the public wants .

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