A smirk moonwalked across 21 year-old Justin Timberlake’s face as he weighed in on the hot topic of Britney Spears’s virginity. “Sure,” he said with maximum sarcasm when asked if Britney had held true to her vow to stay “pure” until her wedding day. And then he burst into a wolfish laugh. He was having the time of his life.
It was November 2002 and esteemed US broadcaster Barbara Walters was grilling Timberlake about the private life of Spears, with whom he had very publicly broken up with several months previously. It seemed to be slut-shaming dressed up as journalism. And Timberlake didn't seem to mind.
The strange exchange – which would thankfully be unthinkable today – came at the end of a conversation in which Timberlake seemed to talk more about Spears than Justified, the debut album he was supposedly promoting. By way of encore he then played Walters a brand new song, Horrible Woman. “I thought our love was so strong / I guess I was dead wrong,” he crooned like a bargain-basement Sinatra. “But to look at it positively, hey girl / At least you gave me another song about a horrible woman.”
Two decades ago, bullying Britney Spears was a popular public pursuit and Timberlake got a free pass for his cruelty. The wheel has now assuredly turned with Timberlake’s part in Spears’s ritualised humiliation spotlit in the New York Times documentary Framing Britney Spears (just aired on Sky Documentaries). Timberlake now 40, quickly apologised to Spears for how he treated her. In a two-for-the-price-of-one mea culpa he also sought forgiveness from Janet Jackson over the 2004 “Wardrobe malfunction” Super Bowl debacle.
“I've seen the messages, tags, comments, and concerns and I want to respond,” he wrote on Instagram. “I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right. I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism.”
It would be nice to think that Timberlake was acting out of the goodness of his heart. But of course he has come out with his hands up only after a social media backlash, prompted by Framing Britney Spears. Without the public pressure, what are the odds that he would have suffered a crisis of conscience?
The upsetting takeaway from Framing Britney Spears is that everyone did well out of Spears, except Britney herself. The greatest pop star of the late Nineties and early 2000s was objectified, scorned as “trailer trash” and excoriated as the world’s most terrible parent. And nobody arguably profited more handsomely from the Bashing Britney business than Timberlake, whose November 2002 hit Cry Me A River not only references their split in the lyrics but came with a video in which a Britney look-alike “cheats” on our guy.
Four years later, he was at it again with the ballad What Goes Around… Comes Around . While Tmberlake said the song was based on a friend's romantic experience, many listeners believed it to be more personal – a revenge-on-your-ex epic romp dripping with bitterness.
“Hey, girl, is he everything you wanted in a man?,” sang Timberlake. “You know I gave you the world /You had me in the palm of your hand.”
What Goes Around… Comes Around is, to be fair, is fantastic – especially when Timberlake’s producer, Timbaland, swoops in on the chorus. But by then redemption was too late for Timberlake, had dined out to his heart's content on Britney and her supposed romantic backstabbing.
Pop’s golden couple had first met in the early Nineties. Both were aged 11 and had auditioned successfully for Disney kids’s show, the Mickey Mouse Club (it was Britney’s second try out – she was rejected first time for being too young). They would reconnect at the end of the decade, when Timberlake was in NSYNC – a sort of frat party Take That – and Spears, then an up-and-coming pop star, was billed as support on their 1999 arena tour.
Soon they were a couple – or rather the couple, pop’s answer to Brad Pitt and Jennifer Aniston or David and Victoria Beckham. They could even get away with turning up at the 2001 American Music Awards in matching denim. That’s how glamorous they were, how unbreakable their love seemed, how immune they were to the basic laws of fashion.
Or so it appeared. But by the end of 2002 the relationship had ended. Rumours reached the American gossip press that Spears had cheated on Timberlake with her choreographer, Wade Robson. That November Timberlake released Cry Me A River, with the “Britney” video. And then his career took off.
It reads like a straightforward showbusiness narrative. Two glamorous young stars fall in love, the relationship sours, he pens a searing break-up song. But because this is real life, the facts are messier. For one thing, Cry Me A River was actually written when Justin and Britney were still together, according to Timberlake.
His version of events was that Spears had said something about her boyfriend on stage that annoyed him – and that, in the studio, he vented to Timbaland, who encouraged him to put it in song. “I was like, 'Man, don't worry about it' and he was like, 'I can't believe she did that to me' and he was like, 'You were my sun, you were my earth…'”
As for the nakedly exploitative move of putting “Britney” in the video, Spears subsequently revealed that Timberlake called her to warn her Cry Me A River would feature a lookalike. The record label even offered her a veto. Not realising how explicitly it would demonise her, she told Timberland it was his life and career and that he should do whatever he wanted.
“He called me up and wanted to supposedly get back together or whatever, but behind it was, and by the way, you’re in a video that’s coming out,” she told Rolling Stone in 2011, in a feature inevitably headlined Britney Spears Finds It Hard To Be A Woman. “That kind of got slipped in. “Don’t worry about it. It’s not a big deal.” So the record label called and said, “If you want to change this, you can.” I had the power to say no to the video. But I didn’t, because I thought, “Hey, it’s your video.”
The interviewer asked her had she seen the video at the time she gave it the green light. “I hadn’t seen it. Then it came out, and I said, “I should’ve freakin’ said no to this sh*t!” I was so like, “Whoa. What is going on right now?” But, hey. And I said, “Why did you do this?” He goes, ‘Well, I got a controversial video.” And I was like, “You did. Yay for you.” So he got what he wanted. I think it looks like such a desperate attempt, personally. But that was a great way to sell the record. He’s smart. Smart guy.”
The consensus today is that Timberlake leveraged the break-up with Britney to super-charge his post-boyband profile. His first solo single Like I Love You had flopped that August and had Cry Me A River done likewise he may well have slunk back to NSYNC. But with the Britney-themed promo bringing with it a whiff of scandal, Cry Me A River took off. And Justin Timberlake became the global pop star we know and love (or at least used to love).
Casting himself as the wronged-one in the relationship, also had the effect of presenting Britney as the villain. Was that his ulterior goal? In addition to giving Timberlake a leg up in the charts, was he trying to take revenge against her? Was this about business and pleasure?
“The break-up was absolutely heartbreaking for me,” Timberlake told the Telegraph in 2003. “I can't just have meaningless relationships with women. I have to find Miss Right in order to have a relationship. There's got to be that big moment when she comes along."
On the promotional circuit for Justified, Timberlake never once refused to answer a question about Britney. Indeed, watching the old footage a certain glee appears discernible whenever her name is brought up. This takes us back to that fateful Barbara Walters interview where he tries to pass himself off as a gracious ex while hinting heavily that Britney cruelly broke heart.
“I remember when we decided we were going to go our separate ways, we sat down and I said to her, “If there’s ever a moment where you ever need me, you can rest assured that I will be there, because I love you as a person and I will always love you,”” he told Walters, displaying a dramatic range conspicuously missing from his underwhelming acting career.
She then asked him if it was true that Britney had cheated on him. He didn’t go out of his way to deny it. “I promised her that I wouldn’t say specifically why we broke up.”
A generous reading of the situation would be that Timberlake was just a kid at the time – and still finding his way as a public figure. However, years later, he still had it in for Spears. In 2006, he more or less confirmed that he was taking revenge against her, telling GQ that “I felt like she had a couple of opportunities to just sort of stick up for me, and she didn't. Which is ﬁne. But at that time, you know, I fought back, and that's the way I fought back. I used my mind. I came up with a song.”
He had already revealed that he and Spears had had “oral intercourse”, telling the radio station Hot 97, “I did it. I'm dirty”. Without wishing to be old-fashioned, whatever the opposite of a gentleman was, it was starting to look a lot like Timberlake. As recently as 2013, performing on stage he said, “Sometimes in life, you think you found the one. Then you find out that she was just a bitch.”
Timberlake married Jessica Biel in 2012 and has since cultivated a cuddly, dad-next-door image (as well as trying and failing to turn the lumberjack shirt into a pop trend with 2018’s Man of The Woods album). But times change, and now it is he, not Spears, who is suffering the wrath of the public. Perhaps he is finally beginning to understand what he put her through.