Pop music's golden couple was pretty much the cutest thing you ever did see when they began dating in 1999. They shared anecdotes about how they developed mutual crushes while working together as tweens in 1992 on The All-New Mickey Mouse Club (he was her first kiss!) before reconnecting seven years later.
At the time, Spears was about to break through with her multiplatinum debut ...Baby One More Time that made school uniforms cool and parents aghast and Timberlake was hard at work on 'N Sync's follow up to their equally successful self-titled release.
Theirs was a connection filled with all the passion and excitement of first love—"I was infatuated with her from the moment I saw her," he later told GQ—plus a heady rush of success with the pair dominating in a space also occupied by the likes of Christina Aguilera, Jessica Simpson, Destiny's Child and the Backstreet Boys.
They performed during the Super Bowl halftime show and appeared together on Saturday Night Live. They collected more trophies than they could possibly display in their shared Hollywood Hills home and almost managed to make matching denim-on-denim-on-denim look good at the American Music Awards. (They didn't, but if anyone could have pulled off jeans as formal wear it would have been music's flaxen-tressed power duo.)
"I love him from the bottom of my heart. As far as love is concerned, with him, too much is not enough. He's everything," Spears mused in a September 2001 interview with The Guardian. "It is a deeper love now than when I was younger. Like, we've gone through so much together and we've known each other since we were 12 years old. We know each other inside and out."
Until one day, seemingly out of the blue, they just didn't, news of their March 2002 breakup tearin' up fans' hearts.
Decades before joint split statements posted to social media were standard, 21-year-old Timberlake and 20-year-old Spears were left to explain what the f--k happened over and over and over again. (And once more, for good measure, Spears divulging their relationship drama and their decision to get an abortion amid other truths in her October 2023 release The Woman in Me.)
Almost immediately, cheating rumors formed, Timberlake helping to fan those particular flames with cagey quotes about how he "promised her" he wouldn't share what happened and his November 2002 release of "Cry Me a River," a tale about a heartbroken, wronged man that the singer said "was written in a time of pain."
For Spears, the struggle was more than just losing the person she'd been envisioning forever with since she was a teen. "I'm still hurting, but I am trying to see it as an experience," she reflected to The Sun in 2002. "The worst thing is everyone wants to talk to me about it. Everywhere I go people are asking how I am."
Basically, as Spears reflected in an Instagram post in April 2020, some 18 years after the fact, "We had one of the world's biggest breakups."
With Timberlake eager to promote his new solo effort Justified ("At this point in my life, if you really want to know who my girlfriend is, it's those 13 songs on that CD," he noted to Barbara Walters), the post-separation press gauntlet wasn't all that bad for him.
"It's funny because every time someone interviews me they're like, 'You know, listen, I really hate to ask this, but…'" he told E! at the time, explaining why he was unbothered by the standard line of questioning. "For me, I'm really indifferent."
After all, he did have a product to push, his initial single off his November 2002 debut disc, "Like I Love You," only reaching No. 11 on the Billboard charts. And if that meant sharing anecdotes about the heartbreaking end to his first-ever serious romance, he'd do it with a charming smile and just enough transparency for fans to infer that he was the wronged party.
"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 recalled, speaking with Walters for 20/20 in November 2002. "But I also said, 'Look, no matter what we say at this point people are going to speculate things, and I could really get myself in a horrible position if I was to say something and somebody misinterpreted, because that happens all the time.'"
He certainly didn't want to give anyone the wrong idea, he continued, so he'd just share that he'd "promised her that I wouldn't say specifically why we broke up."
But should anyone care to read between the lines, he was happy to play a few bars from "Horrible Woman," a new track he'd written that included the lyrics, "I thought our love was so strong / I guess I was dead wrong / But to look at it positively, hey girl / At least you gave me another song about a horrible woman."
Asked outright about the cheating accusations, he told Walters, "Honestly, I mean, you know, we're not perfect. I don't judge anybody."
There were plenty of others to handle that.
In "Framing Britney Spears," the 2020 episode of FX's The New York Times Presents docu-series, we were all reminded how crassly the twentysomethings' sex life was discussed in the wake of their split and just how easily Spears was slotted into the role of villain.
Timberlake could hardly manage a straight face when Walters brought up a quote Spears had given saying "good morals mean waiting to have sex until after you've been married." Asked if they'd "lived up" to that messaging during their relationship, he cracked, "Sure," with a laugh before staring directly into the camera and repeating himself: "Sure."
He'd already addressed the subject two months earlier on the Star and Buc Wild Morning Show. When asked, "Did you f--k Britney Spears, yes or no?", he responded, "Okay, I did it!" prompting the gaggle of bros to break out in raucous cheers.
By the time he covered Details in December 2002, the mag was proclaiming, "Can we ever forgive Justin Timberlake for all that sissy music? Hey...at least he got into Britney's pants."
The age of enlightenment this was not. With the #MeToo movement and terms like "sex-positivity" still a couple of decades off, Timberlake was hailed as a conquering hero; Spears, a questionable role model for her young fans.
And though the "Sometimes" singer remained silent on what did or did not take place behind closed doors at the time, she confessed to Diane Sawyer during that much-maligned-in-retrospect November 2003 interview, "It was a really weird time."
Listening to her former boyfriend gleefully dish on "what we did together, sexually and stuff," she continued, "I just felt very exploited and very weird. I was like, 'Why is he going on these shows and they're asking him and he's talking?' You know, but I'm sure, just like right now, you're asking me about it and I'm talking about it and it just kind of comes out."
Because there was little time for the pop princess to avoid the subject. She had her own disc to promote—2003's In the Zone serving as her fourth release in less than five years. Only now she'd have to do it whilst dodging questions about her ex-boyfriend's music.
"Cry Me a River," Justified's second single a track largely assumed to be an autobiographical take on their split likely would have eclipsed its predecessor "Like I Love You," with its lyrics alone: "You don't have to say what you did / I already know, I found out from him."
But when the video dropped, featuring 18-year-old blonde model-actress Lauren Hastings, a Spears doppelgänger down to the newsboy hat, well, it seemed awfully deliberate. Suddenly Timberlake had a runaway hit and Spears had some 'splaining to do.
Timberlake had reached out to inform her that he'd cast a lookalike to appear opposite him, but it was still tough to process. Seeing the video while on vacation, "I was kind of in denial, like, I went into this whole denial phase or whatever," she explained to Sawyer. "I don't want to judge him or anything like that, because that's the way he had to deal with what happened. And that's fine."
Still, she continued, "I know if I was in a relationship and something happened, I just, I couldn't really go there." Sure, her single "Everytime" in which she sang "My weakness caused you pain / And this song's my sorry" seemed to be about Timberlake. But, as she stammered to Sawyer, "I'll let the song just speak for itself."
Not that it mattered. The narrative had already been set.
A September 2002 Us Weekly cover asked, "Did she betray him," and every action the two made from there was seen as a tactical move in their ongoing war.
When Spears stepped out in a shirt proclaiming "Dump Him," fans speculated the directive was aimed at Timberlake's then-rumored flame Alyssa Milano. A hang out with Backstreet Boys' Nick Carter? An attempt to make her ex jealous.
Then came the "Cry Me River" of it all. Despite Timberlake claiming during the TRL drop that "the video is not about her," it sure seemed that way. "People treated her like she was the school slut and he was the quarterback," former MTV VJ Dave Holmes recalled of the hysteria on "Framing Britney Spears," noting how Timberlake "weaponized the idea for one of his singles."
By the time Spears sat down with Sawyer nearly a year later, she'd all but been labeled the transgressor. As the veteran journalist put it in her interrogation, "You did something that caused him so much pain, so much suffering. What did you do?"
Doing her best to remain diplomatic, Spears simply responded, "We both are really young and it was kind of waiting to happen. I will always love him...he is such a great person,"
As for whether she'd been unfaithful, she told Sawyer carefully, "I think everyone has a side of their story to make them feel a certain way…and I'm not technically saying he's wrong but I'm not technically saying he's right either."
Technically, that's the closest we ever got to an answer, neither side elaborating further. Until this past fall, with Spears alleging in her memoir that Timberlake cheated on her.
As for Timberlake, he continued to reference his famous ex long after she'd moved on, first with now-ex-husband Kevin Federline, dad to her sons Sean, 18, and Jayden, 17, then a series of almost Mr. Rights including estranged husband Sam Asghari.
Speaking on Spears' now-infamous kiss with Madonna at the 2003 MTV Video Music Awards, Timberlake told Ellen DeGeneres, "I don't think I was disgusted. I think I was just not impressed. I mean, I expected a lot more. It's the VMAs, you know?"
And in 2006, four years after their breakup, when he was more than three years deep into his romance with Cameron Diaz, he returned to the tried-and-true scorned man archetype, dropping "What Goes Around Comes Around" on his sophomore solo album and reflecting on his big breakup in a chat with GQ.
"When we initially parted ways I felt like she had a couple of opportunities to just sort of stick up for me, and she didn't," he explained of that initial resentment. "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."
As an added benefit, his strategy helped transform his own curly-haired, squeaky clean boy band reputation. "One minute Timberlake was a forgotten relic of teeny pop, the next he's making the video for 'Cry Me A River' in which he's stalking his ex and creeping up behind her to sniff her hair," GQ wrote in a 2006 profile proclaiming him their International Man of the Year. "And within the space of a year no one could give two hoots about his New Mickey Mouse Club beginnings. Timberlake suddenly became Trousersnake and he'd done the impossible—he'd become cool."
That he'd done it at the expense of his former girlfriend now seems pretty undeniable thanks to the benefit of hindsight. With "Framing Britney Spears" digging not only into her complicated 13-year conservatorship, but also the harassment and slut-shaming she endured following her split with Timberlake, even he had to admit he hadn't handled the situation all that well.
As fans flooded social media demanding he apologize for using the narrative of their breakup to help launch his solo career, Timberlake issued a mea culpa on Instagram, taking ownership "for the time 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." (He also offered a direct apology to Spears and 2004 Super Bowl halftime co-performer Janet Jackson, who bore the brunt of the criticism for the nipple shield-bearing mishap that launched the term "wardrobe malfunction.")
Among those paying attention was Spears, who long ago let her teenage sweetheart off the hook for his transgressions, often using his songs as the soundtrack for her Instagram dance videos and even admitting that he remains on the list of her dream collaborators.
Though with her book and his newest release "Selfish" once again riling up their fanbases, will they, oops!...reopen their feud again? After Timberlake took to the stage in a Jan. 31 concert announcing he'd "like to take this opportunity to apologize to absolutely f--king nobody," Spears seemed to respond with a Feb. 1 post before making her Instagram profile private.
"Someone told me someone was talking s--t about me on the streets!!!," she wrote. "Do you want to bring it to the court or will you go home crying to your mom like you did last time??? I'm not sorry!!!"
Perhaps she's getting ready to give us, give us more details in another book.
(This story was originally published on Saturday, Feb. 20, 2021 at 12 a.m. PT.)