At the turn of the millennium, Britney Spears and Justin Timberlake's teen romance entranced tabloid culture like little else.
Timberlake, the pin-up boy-band member, and Spears, the pop-star phenomenon, were a match made in publicity heaven and, eventually, personal hell.
Nearly two decades on from the demise of their romance, the exes' love affair is back under the spotlight.
Spears has a new memoir coming out, The Woman In Me, and by all reports a large portion of the book will unpack her former relationship with Timberlake.
In an extract shared with PEOPLE this week, Spears said that she fell pregnant when they were dating.
"It was a surprise, but for me, it wasn't a tragedy. I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I'd anticipated," she wrote.
"But Justin definitely wasn't happy about the pregnancy. He said we weren't ready to have a baby in our lives, that we were way too young."
Watch the trailer for 'The New York Times Presents Framing Britney Spears' here. Post continues below.
Spears said that without Timberlake's opinion, she would have continued on with the pregnancy.
"If it had been left up to me alone, I never would have done it. And yet Justin was so sure that he didn't want to be a father," she said. "To this day, it's one of the most agonising things I have ever experienced in my life."
Following this report, Timberlake has not responded publicly to the news of Spears' book, which is set to be released on October 24.
Back in 2021 though, Timberlake did make a comment.
His former relationship was at the centre of public consciousness, following the release of the documentary The New York Times Presents Framing Britney Spears.
The documentary delved deep into the life and career of Spears and offered a fresh lens for examining how the singer was treated by not just the media, but also her close circle. In light of the documentary, fans of the #FreeBritney movement called for several high-profile people to apologise for the role they played in the treatment of Spears - Timberlake included.
In a statement issued via Instagram, the former NSYNC singer began, "I've seen the messages, tags, comments, and concerns and I want to respond..."
As for why Timberlake apologised to Spears, nearly 20 years on, here's what happened.
The 'Cry Me A River' controversy.
In the wake of their breakup in 2002, the tabloids reported rumours that Spears, then just 21 years old, had been unfaithful to Timberlake.
Timberlake seemingly confirmed this with his 2002 single 'Cry Me A River', with the famous lyrics: "You don't have to say, what you did / I already know, I found out from him / Now there's just no chance".
The music video - released only months after the breakup - paints the picture of Timberlake as a heartbroken lover who is seeking revenge over his cheating ex. A woman with a striking resemblance to Spears was cast to play the ex.
In an interview with Rolling Stone, Spears implied she felt betrayed by the 'Cry Me A River' music video.
"I think I was in shock, to be honest. I didn't know what to say, what to do. That was the last thing I ever thought somebody might do. I was really shocked sh*tless. But you live and you learn...
"He called me up and asked me if it was OK... 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.' That kind of got slipped in. 'Don't worry about it. It's not a big deal'," she continued.
"I hadn't seen [the music video for 'Cry Me A River']. 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."
When she was a teenager, Spears famously said she was 'saving' herself for marriage. The world was obsessed with the singer's virginity, even more so because she was in a relationship. But Timberlake revealed after their breakup that he had, in fact, had sex with Spears.
During a radio interview for Star and Buc Wild Morning Show in 2002, Timberlake was asked: "Did you f*** Britney Spears?"
Timberlake laughed, before responding: "OK, I did it."
In a subsequent interview with New York radio station Hot 97, the DJ said he would play Timberlake's then-single Like I Love You thirty times a week if the singer confirmed he had sex with Spears.
Timberlake confirmed he'd had "oral intercourse" with her.
"I did it. I'm dirty. I'm in so much damn trouble, man. I'm going to get calls from my mother," he responded, laughing.
A media storm ensued, with much of the commentary painting Spears as a 'sl*t'.
Re-visiting these interviews, the Framing Britney documentary accuses Timberlake of "weaponising" his breakup with Spears to launch his solo career, seemingly not caring if he 'sl*t-shamed' her along the way.
"The way that people treated her, to be very high school about it, was like she was the school sl*t and he was the quarterback," New York Times critic at large Wesley Morris explained in the documentary.
The Diane Sawyer interview.
The infamous Diane Sawyer interview demonstrated the extent to which Timberlake had sucessfully peddled his 'wounded lover' narrative and made Spears the villain.
During the 2003 interview, which promised a "no holds barred" insight into the popstar, Spears was solely blamed for their breakup.
"[Timberlake] has gone on television and pretty much said you broke his heart," the journalist said, after Spears had previously asked to take a break when the topic of Timberlake was brought up.
"You broke his heart, you did something that caused him so much pain, so much suffering. What did you do?"
"I was upset for a while," Spears responded. "I think we were both really young and it was kind of waiting to happen, and I will always love him. He will always have a special place in my heart."
Sawyer went on to ask if the rumours that she was unfaithful to him were true.
"I think everyone has a side of their story to make them feel a certain way," Spears said. "I'm not technically saying he's wrong but I'm not technically saying he's right either. Wow, this is really awkward right now."
Justin Timberlake's 2021 public apology.
In light of the New York Times documentary, social media was awash with calls for Timberlake to apologise to Spears.
"The industry is flawed. It sets men, especially white men, up for success. It's designed this way. As a man in a privileged position I have to be vocal about this," he wrote.
"Because of my ignorance, I didn't recognise it for all that it was while it was happening in my own life but I do not want to ever benefit from others being pulled down again."
The comments were filled with criticism that the apology was "too little too late" and that he'd lumped two apologies into one by discussing both Janet Jackson and Britney Spears.
This same year, Timberlake also threw his support behind the push for his ex's conservatorship to end.
He posted a Tweet, part of which referenced the claim from Spears that she had been forced by her conservators to have an IUD implanted, to prevent her from having more children. The IUD had been against her wishes.
"After what we saw today, we should all be supporting Britney at this time. Regardless of our past, good and bad, and no matter how long ago it was… what's happening to her is just not right. No woman should ever be restricted from making decisions about her own body," Timberlake Tweeted at the time.
One can only assume that when Spears' memoir surfaces, more stories will be brought to the world's attention.
This article was originally published in 2021 and has since been updated with new information.
Feature Image: Getty.
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