I’m getting ready for a radio interview. He was scheduled to appear on The Star & Buc Wild Morning Show on Hot 97, the country’s most important hip-hop station. Star and Buc Wild, the hosts at the time, were the ultimate tastemakers. Their radio show was known for grilling superstars like A Tribe Called Quest, Busta Rhymes, and Nas in an irreverent manner. For their bold, direct interviewing approach, they’d established a sizable following. Meanwhile, Timberlake had recently broken up with both his boy band *NSYNC and his fiancée, Britney Spears. He’d just released his solo single “Like I Love You,” which included Clipse, a week before. His austere public character was undergoing a profound transformation.
“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. “Yes or no? Come on, man.”
Timberlake paused for a brief moment, letting out an awkward laugh. “Oh man.” His inflection shifted, and he exclaimed, “OK, I did it!”
Star recalls the behind-the-scenes events of that interview a decade later. “There were maybe five people in that room with us,” he recently told me, “and two of those individuals were representatives from Jive Records,” which was at the time both Timberlake’s and Spears’ record company. “I believe the other three were members of Justin Timberlake’s management staff.” Despite Timberlake’s attempts to self-brand as a “R&B” vocalist rather than a pop star, Hot 97 wasn’t too keen on playing his music back then. Star, on the other hand, liked him. “I said, ‘Hey dude, I’m not trying to squeeze you or be disrespectful, but you and Britney recently broke up,” he explained. “He didn’t want to talk about it, but I told him, ‘Look, I swear to you, I’ll play this goddamn song of yours twice a day for two weeks if you could just give me some information here.’ ” “He practically flushed beet red,” Star added of Timberlake’s smile. “‘Hey dude, I’ll play it four times a day,’ I said. “Goddamn it, Justin, I’m going to play this record five times a day, what do you think?” I remarked. Star explained that they were merely kidding around. Then Justin shocked the tabloid world with a quote.
Timberlake was the sensitive ex–boy bander in 2002, a devastated heartthrob who was too polite to speak badly of his former but clever enough to burn her in his songs (without naming her, of course). Simultaneously, there were accusations that he told choreographers, “Dude, smell my fingers,” to brag about having sex with America’s unachievable sweetheart: the objectified and infantile vestal virgin next door. It was a big hit to Britney’s brand when Justin acknowledged to having sex with her; at the time, she had told the press she wanted to try to remain celibate until marriage. Timberlake’s reputation has just lately been tarnished by the way he acted and spoke during the time, thanks in part to the success of the New York Times documentary Framing Britney Spears.
The discussion is sure to continue: on Friday, The New York Times will release a new documentary about Timberlake’s historic Super Bowl encounter with Janet Jackson. It’s a stark reminder of his role in the performance, its aftermath, and the media’s ongoing examination of female artists whose sexuality was inextricably linked to their image. Justin Timberlake of the 2000s looks a lot different now, twenty years later, in a vastly different cultural milieu.
Between Britney and Janet, Justin has skated through a slew of crises that have had disastrous PR consequences for the ladies in his life. Timberlake’s boy-next-door persona was bolstered by his incredible musical talent—and make no mistake, he is one of the best performers in modern history—and it lasted for decades, despite evidence to the contrary. The current reckoning around him feels like a cultural exorcism, a chance to purify ourselves of the ills he now represents to many through the boy band vessel. But behind the scenes, he was both a savvy self-promoter and a blank, withholding figure at the center of a tumultuous situation, surrounded by publicists, media, and managers who were all working to shape his image. Timberlake has become the perfect embodiment of a bygone period in which men like him were rewarded—until they weren’t.
Timberlake was it at the millennium’s turn, when apprehension of an unknown future could be soothed by the sugary-sweet five-part harmonies of Y2K boy bands. The zenith of *NSYNC’s career. Timberlake, a good-ol’ mama’s boy from Shelby Forest, Tennessee, was born with a symmetrical face and thick hair that were raised to the gods and given the look of ramen.
He was born in the year 1981. His stepfather, Paul Harless, was a Baptist church choir director, and his mother, Lynn Harless, was on her way to becoming one of America’s most famous stage parents. (In a 2006 Rolling Stone cover story, Lynn referred to Justin’s biological father, Randy Timberlake, as the “sperm donor,” who played bass and sang high harmonies in a bluegrass band.) She attributes her son’s virtuosity to him.) Timberlake was cast in Disney’s All-New Mickey Mouse Club at the age of 12. He was a star for two seasons. The show was discontinued when Timberlake was 13, and the following year, Chris Kirkpatrick of *NSYNC phoned Timberlake’s mother about forming a new singing group. *NSYNC’s success was boosted by a Disney Channel endorsement: No Strings Attached, released in 2000, sold over 1.1 million copies in its first day and over 2.4 million in its first week, breaking a 15-year record. And Justin was the man in charge.
He was also a child when he entered the entertainment industry, and he was exploited by it: by manager Lou Pearlman, who had him and the other boys sign what litigator Helene Freeman dubbed “the worst contract in music history,” earning pennies on the dollar for the long hours they worked, according to fellow band member Lance Bass’ memoir. Timberlake told Rolling Stone in 2006 that he believes the band is being “monetarily raped by a Svengali.” A seminal Vanity Fair article the following year claimed that Pearlman had been far more than financially exploitative; he had sexually molested many youths whose careers he had helped launch. (Unlike the other members of *NSYNC, such as Lance Bass, who published The Boy Band Con: The Lou Pearlman Story, a documentary detailing Pearlman’s financial adventures in 2019, Justin Timberlake has rarely spoken about the manager.)
It’s also important to note that, as a product of the child-star system, Justin most likely received media training during his teens, which included internalizing publicity methods designed to help him stay relevant, such as staying quiet and listening to the pros. Silence allowed his extraordinary gift to speak for itself. It also meant that his public persona would appear to be completely neutral and open to anyone.
Former MTV VJ John Norris recalls interviewing Timberlake on the 1999 *NSYNC tour, which featured Britney Spears as the opening act. Compared to some of the other band members’ “frat guy” attitudes, Timberlake sounded less silly and more self-aware. Timberlake gave Norris a ride in his new automobile at one point. The initials “WWJD” hung on his rearview mirror. “I was such a heathen and knew so little about being a good Christian lad,” Norris remembered, “that I knew nothing about the statement, ‘What would Jesus do.'” “I was like, ‘What is that thing hanging there?'” says the narrator. ‘Oh, it’s just a thing for, like, checking oneself,’ Justin explained. ‘What do you mean?’ I inquire. Is there a meaning to it?’ He was adamant about not going into it.” JT had the foresight not to make an openly religious statement; he was “quite stubbornly anti-political” and “singularly disinterested in going too controversial” from an early age, according to Norris. (Representatives for Timberlake did not reply to several requests for comment.)
This was what the culture required of huge pop singers in the early 2000s. Apolitical speech that leaned conservative more frequently than not, the kind of patriotism that professed not to take sides after 9/11. Consider Jessica Simpson, Christina Aguilera, and Hilary Duff, the next generation of Disney Channel stars. If and when controversy arose—as in 2003, when Madonna and Spears kissed in front of a camera aimed on Timberlake in the audience at MTV’s Video Music Awards—it was almost always orchestrated. It was staged controversy, obedient to the audience, and orchestrated without asking the performers to adopt a political stance. (Think of it this way: In preparation of the US invasion of Iraq, Natalie Maines of the Dixie Chicks informed a crowd in London that her band was “ashamed the president of the United States is from Texas,” and the group was blacklisted from radio, effectively ending the Dixie Chicks’ career. CD burnings were arranged as a form of protest.)
The interaction between celebrities, paparazzi, and tabloid media was particularly symbiotic and toxic during that time. The supermarket magazine sector was fiercely competitive before the internet (TMZ, Just Jared, and PerezHilton.com didn’t debut until the mid-2000s). Exclusives were the lifeblood of magazines like Us Weekly, People, and Star, which necessitated regular haggling with celebrities and their publicists. Stars, for their part, were reliant on tabloids to build their own narratives.
After *NSYNC broke up in 2002, JT released “Like I Love You,” a cut off his upcoming album Justified, which he recorded with the Neptunes and Timbaland, and which Star vowed to play numerous times a day on Hot 97. Many people today say that JT ascended to solo prominence on the backs of Black artists without properly crediting them. Just a few years before the infamous Super Bowl, Janet Jackson was featured on a late album cut called “(And She Said) Take Me Now.”
“Like I Love You” peaked at No. 11 on the Billboard Hot 100, an excellent achievement for any artist, but not enough of an impact for him as a solo artist, given his band’s ubiquity. It also came with a new, carefully constructed image: Justin Timberlake was suddenly the bland everyman with a bite, who had been wronged by his scheming ex-girlfriend.
It’s understandable that JT’s management realized his separation with Britney Spears would generate a lot of attention. If he couldn’t get into the Top 10 on his own, the story of America’s favorite power couple breaking up, with JT playing the tender-guy victim, would do the trick. According to tabloid sources from the time, Timberlake was not a big draw for readers on his own. “He’s pretty much a closed book.” One former celebrity magazine editor from the 2000s told Slate, “We always had difficulties generating a lot of interest, and the curiosity was always in reference to whatever he was dating.” However, the Britney Spears breakup was a once-in-a-lifetime opportunity for Timberlake and his team to play nice with the press. “I believe we only had about five minutes with him and a photographer he knew.” “Britney was sleeping with dancers or something like that,” the tabloid editor recalled, but added, “it was certainly his people going in front of the issue and being proactive.” (Infidelity rumors have never been substantiated, yet they continue to surface.)
He went on to say, “The whole thing was a post-breakup cooperation.” “And we were joking around about Britney cheating on him.” That was the entire plan.” Given Timberlake’s new sorrow album’s impending release, the tabloid editor suspected “it was all very planned to be a revenge narrative.”
Justin’s first solo success, “Cry Me a River,” featured a video-actor lookalike and was a not-so-thinly-veiled indictment of Britney Spears. He sang, “You don’t have to mention what you did/ I already know, I learned from him.” “You said you loved me, so why did you abandon me?”)
It reinforced his reputation as a sensitive solo artist. His sound was reminiscent of a white neo-soul Usher, largely influenced by the Neptunes and Timbaland’s production, and his mindset was that of a glamorous, single, suit-wearing bachelor. In two hours, he claims, he wrote “Cry Me a River.” With headlines like “solo in every aspect, the gorgeous singer sets the record right,” celebrity media inclined to side with “Team Justin.” (A 2002 Details cover line may be the best depiction of the perverted cultural mores of the time: “Can we ever forgive Justin Timberlake for all that sissy music?” At the very least, he got into Britney’s underwear.”) Meanwhile, headlines such as “Did she betray him?” “Britney cracks up!” and “Boozing Britney out of control” flooded the internet. As a result, her own interviews were used to mitigate the damage: She is not a drug user. She like red wine but never overdoes it. She’s still the same girl we’ve known since we first met her.
His relationship with ’00s tabloid culture is complicated by the fact that he wasn’t always cooperative with the publications that backed him up. “Justin detested the paparazzi. Danny Ramos, a former paparazzi, remarked, “I didn’t give a damn about them.” “I couldn’t approach him and say, ‘Hey Justin, how are you?’ He’ll almost certainly have me in a headlock.
“When you combine Justin Timberlake and a paparazzi, it’s an explosion,” Ramos added. “This isn’t going to go over well.”
It was meant to be aggressive, and it was. Justin is seen punching paparazzi cameras out of the hands of videographers in recordings from the mid-2000s, particularly around the time he dated actor Cameron Diaz (aka, a year after he broke up with Britney). These are the kinds of violent, protective acts that would have made front-page news if Britney had carried out the attack—which she did, of course—like when she struck Ramos’ truck with an umbrella.
“I call it ‘teasing,'” Ramos stated, referring to superstars such as Paris Hilton, Lindsay Lohan, and Britney Spears. They desire it one minute and then don’t the next. And it wasn’t like that at all with Justin. “Get that shit away from me,” Justin said. It was fundamentally gendered—Britney, Paris, and Lindsay couldn’t change their opinions about photographers, whereas Justin was admired for his outrage. That doesn’t even take into account the pressure they must have felt as young women to get along with the camera crews who knew where they lived and followed them around on a regular basis.
Ramos, for one, has begun to engage with this dynamic in a manner that he claims he didn’t back then. “There was a double standard,” he explained. “You may compare that to masculine chauvinism at the time.” ‘Let’s just pick on the gals,’ it was like. It felt like I was being bullied. And the males were not as targeted as the females.”
Timberlake’s staff was pushing a breakup narrative, and the mainstream media got on it as well. Justin gave a mysterious but sympathetic reason for his separation with Britney in an iconic interview with Barbara Walters on ABC News’ 20/20 in 2002: “We’re not perfect. I don’t pass judgment on anyone.” After that, he performed an unpublished song. He sang, “Frankly, honey, you ain’t worth the petrol in my BMW.” “But, on the bright side, you did give me another song about a bad woman/ And that’s you.” Britney was unfaithful and harsh, and he was once again a man scorned. Justin laughed and responded, “Sure,” when Walters asked if he and Britney kept her promise to wait until marriage to have sex. “All right,” Walters said with a chuckle. I posed the question, and you responded, correct? “Both of us accomplished our jobs.” (“I’ve only ever slept with one person in my life, and I’ve been with Justin for two years.”) He seemed to be the one. But I was mistaken. Britney told W magazine in 2003, “I didn’t think he was going to go on Barbara Walters and sell me out.” “That breakup was the most painful thing I’ve ever gone through.”)
Britney wasn’t the only one who had to deal with the fallout from JT’s media attention. Timberlake was able to return to the limelight uninjured after grabbing Janet Jackson’s chest at the 2004 Super Bowl halftime show—a move that was supposed to reveal red fabric but instead displayed her breast. “Hey, man, we love giving y’all something to talk about,” Justin told Access Hollywood after the concert. Janet was barred from the Grammys a week later, and her career never fully recovered. Meanwhile, Justin gave a performance and took home the prize for Best Male Pop Vocal Performance. Even when the New York Times declared that it will focus its documentary on this episode, headlines referred to it as the “Janet Jackson Super Bowl Scandal.”
His star continued to rise over the next few years. Timberlake effectively reworked “Cry Me a River” in “What Goes Around… Comes Around” on his solo album FutureSex/LoveSounds, released after the Super Bowl in 2006. One critic stated, “Give him credit for being one of the few white males still bold enough to compose Black music, even if he hasn’t yet invented a persona compelling enough to live up to his music.” “Tense drum machines, high-pitched synth squiggles, and staccato funk bass lines update the early-eighties Minneapolis sound.” Underneath the cynicism of that assessment, Justin was praised for good compositions born of a love for Black music.) The songs were expertly written, a lesson in how to mature after being a teen pop phenomenon. Their message was also a form of self-victimization hidden behind sadness. In “Cry Me a River,” he sung, “All these things folks told me/ Keep messing with my head/ Should’ve picked honesty/ Then you wouldn’t have blown it.” Justin’s subsequent A-list acting roles—Sean Parker in 2010’s The Social Network, Dylan Harper in 2011’s Friends With Benefits, and, of course, his beloved Saturday Night Live comedy, “Dick in a Box”—allowed him to do both: appear caddish and do an act mocking what it means to be a cad.
Timberlake’s golden boy status didn’t begin to wane until nearly a decade later, with the critically panned Man of the Woods. The 20/20 Experience and The 20/20 Experience–2 of 2, JT’s neo-soul albums from 2013, were praised for their consistency—glossy pop by a sensitive and sensual bon vivant. After a musical hiatus, Justin emerged a few years later, sans Armani clothes, to play with folk music iconography, penning his own sermon without any unusual elasticity, like a man in repentance. In his art, he seemed more self-reflective and hazy—the aging American icon leaning into Americana, striving to come off as a matured family man rather than the flashy, heartbroken-yet-suave bachelor he had been for so long. Despite the fact that JT continued to work with producers Timbaland and the Neptunes on the project, it appeared to be a retreat into whiteness—Western, Manifest Destiny–inflected sounds that embraced the fabled masculinity of the great outdoors, flannel shirts and all. The R&B was switched off, and the party was over.
Cultural appropriation had infiltrated mainstream discourse by 2018. Man of the Woods appeared to be constructed in part to convey comprehension of the contemporary situation from the outside. However, the album was a letdown. Justin was known for grandiose pop singles and larger-than-life stadium events, but he lost widespread acclaim when he pared down his image. (At least, his back-to-basics familism endeared him to loyal listeners.) Silas, JT’s son’s name, is Latin for “man of the woods.” “Sometimes the greatest way to say something is to say nothing at all,” they sing on the bridge of one of the album’s better hits, “Say Something,” with Chris Stapleton. Justin’s blitheness was always part of his appeal, but it lacked charisma on record.
Justin Timberlake’s pop-star persona sank in the years that followed. From wonderful reviews to scathing critiques of his self-indulgent albums, the media’s focus switched. Around him, the cultural landscape changed as well. He signed on to work on Woody Allen’s film Wonder Wheel in 2018, telling the Hollywood Reporter that he preferred “not to delve into” the pedophilia claims against Allen. Despite working with Allen, Justin Timberlake donned a Time’s Up pin to the 2018 Golden Globes, when the #MeToo movement dominated cultural debate. He posted a selfie with his wife, Jessica Biel, wearing the pin and captioning it, “DAMN, my wife is hot!” #TIMESUP.”
During a night out in 2019, a paparazzo caught him locking hands with co-star Alisha Wainwright from the film Palmer, and rumors of adultery continued to swirl around him. So he published a clumsy letter addressed to his “wife and family” but plainly intended as public damage management, apologizing for putting them through “an uncomfortable circumstance” but asserting that he hadn’t cheated with his co-star. Then came the year 2021, and the film Framing Britney Spears. Timberlake’s interview with Diane Sawyer was used prominently in the film, igniting new internet rage against him. As a result, he offered a blanket apology to all the ladies he’d injured, whether intentionally or unintentionally. He stated on Instagram, “I have not been great in navigating all of this throughout my career.” “I recognize this apology is a first step and does not absolve the past,” he added, acknowledging that he’d “benefited from a system that condones misogyny and racism.”
Timberlake had plainly realized that his once-marketable silence no longer worked. However, many saw his apologies as a belated and false attempt to take a line after decades of studious neutrality. “I believe the pop zeitgeist, or what real pop fans desire from male pop musicians in 2021, is so different from what Justin Timberlake was: unmistakably male, unmistakably heterosexual,” said Norris, a former MTV VJ. “I believe there are attributes we admire now that a male pop singer could not have had in the early 2000s.” It was not a “feature of Justin’s appearance.” For fuck’s sake, he’s a golfer. Right? In a nutshell, that’s it. Harry Styles is a golfer. “I don’t believe so.” (He does, but that’s beside the point.) Timberlake now writes children’s songs (“Can’t Stop the Feeling!”), voices cartoons (Trolls), and appears in under-the-radar roles that confirm his recurring soft-guy persona (Palmer).