A Timeline Of Britney Spears And Justin Timberlake's Complicated Relationship

In the graveyard of dead celebrity relationships, Britney Spears and Justin Timberlake's long-gone romance stands out. Powered by meteoric career highs and unmatched pop glamour, the former couple ruled the early 2000s. The combined talent in the equation — Spears broke records with her second album in 2000, per Britannica, while Timberlake's boy band NSYNC set down similar achievements with their third album that year, per MTV — made everyone believe theirs was a romance destined for success. The pair's connection went far back into their early teen years on television, long before they became the biggest pop stars of their generation. In a 2001 interview, Spears told The Observer, "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." 

The pop fairytale came crashing down in 2002. In an entirely unprecedented move, both Spears and Timberlake told the press separately that they were no longer a thing (via ABC). Then the media wars began, with Timberlake supposedly claiming the upper hand amid rumors of Spears allegedly cheating on him. Given their inclinations, both stars even released breakup tracks (of sorts) of their own, fueling the frenzy around their rift. As the waters cooled, and the ex-couple moved on to greener pastures over the years, the tensions between them have relatively mellowed — with each even complimenting the other on occasion! Here's a timeline of Britney Spears and Justin Timberlake's dramatic relationship.

Justin Timberlake and Britney Spears were launched to stardom together by the world's most famous mouse. In 1993, the to-be pop icons we cast in the popular Disney television show, "The All-New Mickey Mouse Club," which also kickstarted the showbiz careers of actor Ryan Gosling and singer Christina Aguilera (via Shondaland). This elite club of Mouseketeers sang and danced their way into the hearts of their youth audience for about a year until the show ended in 1994. 

Sarah Elgart, producer of the iconic show, revealed to E! News that the then 11-year-old Spears and 12-year-old Timberlake "worked really hard, and they seemed to appreciate the moment." Senior Mouseketeer Tony Lucca, meanwhile, recalled that "a lot of young love" and "bona fide great platonic friendships" were common on the show. Aguilera, on James Corden's "Carpool Karaoke," hinted that both she and Spears seemed to have had a bit of a crush on Timberlake, who had loads of "swag."  

As adults, Timberlake and Spears have often reminisced about their time on the show where the groundwork for their eventual romance was laid. Talking to Entertainment Tonight in 2019, Timberlake referred to his Disney stint as "the most influential experience [he] ever had," while Spears told the outlet that the show made for "one of the most special times in [her] life." Both said they would be down for a cast reunion. 

If ever there had been any inkling of kiddie love between Britney Spears and Justin Timberlake during their television stint, it became all too apparent to the world when the couple soon graduated to a proper relationship. According to Vogue, the couple went official with their romance in 1999, when Spears was 18 and Timberlake, 19. By then, the two lovebirds were music sensations and their careers were peaking — Spears' as a solo act with her hit debut album "...Baby One More Time" and Timberlake's as part of the boy band phenomenon called NSYNC. There was initially some denial — with Spears saying in a 1999 interview that rumors about her and Timberlake dating were "not true" — but before long, the couple had embraced their relationship in all its glory! 

Years after their breakup, Timberlake revealed that he had eyes for Spears from the start. "I was infatuated with her from the moment I saw her," he said, per KLTV. Spears and Timberlake's highly public romance, which played out between 1999 and 2002, was really a string of iconic moments — from the couple performing together to sporting matching denim outfits (we'll get to those in a bit). In 2001, Spears gushed to The Observer about her then-boyfriend, saying she was "not ashamed at all to say that 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." 

Is a romantic collaboration between two singers really complete if it doesn't culminate in at least one musical collaboration? The 2001 Super Bowl halftime show is etched forever into millennial pop culture memory for just how rousing it was, with NSYNC and Aerosmith facing off to rock the stage in Florida (via E! News). For a rendition of "Walk This Way," the bands were joined on stage by the Princess of Pop, Britney Spears, making for an iconic music moment seen neither before nor since. Spears' arm sock was easily one of the most memorable bits about her roaring performance, and the accessory has since attained legendary status in the annals of Y2K fashion (via EW). 

While the Super Bowl act is unforgettable, there also exists a Spears-Timberlake collaboration recorded on an album for posterity. For Spears' "What It's Like to Be Me," listed on her third album, Timberlake served as co-writer and co-producer, and also gave backing vocals (per MTV). In an interview with The Observer, a besotted Spears was all praises for beau JT's musical prowess, who was also teaching her to play the acoustic guitar: "I hear Justin play something and I'm like, 'Grrr.'" 

By then, Stinky and Pinky — yes, those were the couple's nicknames for each other, which they also once sported across matching jerseys (via People) — had begun sharing a home in Los Angeles. 

It is said that couples who spend too much time together begin to, eerily enough, look alike. Pop stars Britney Spears and Justin Timberlake had a fashion moment to that effect, back when they were a thing. In what is still touted as one of the most surreal moments from Y2K popular culture, the duo turned up at the 2001 American Music Awards sporting a freakishly co-ordinated double-denim look! Per Jezebel, Spears' denim gown was a Kurt and Bart number, while Timberlake's head-to-toe denim ensemble (with a hat, to boot) was a shoutout to the couple's Southern roots. Steven Gerstein, the designer behind the "Mirrors" singer's outfit told the outlet that "it was just two kids, wanting to do something cool, and being super cute, matching. It was kind of like their prom." 

The ghosts of their denim drapes of yore have haunted Timberlake and Spears for years after their breakup. At the 2014 Video Music Awards, Katy Perry and Riff Raff paid homage to the former pop couple by arriving in matched denim outfits that evoked serious nostalgia (via HuffPost). Spears shot a tweet to Perry, "Just when I thought the denim dress had retired....you bring it back! You looked amazing tonight bb" More recently, at a roundtable in 2021, Timberlake said that "the internet won't allow [him] to forget" certain fashion looks, while fellow speaker John Legend chimed in teasing, "Denim on denim ... " 

Britney Spears and Justin Timberlake had attained status as one of the new millennium's hottest "it" couples. So it came as an inconceivable shock when it was reported rather suddenly in 2002 that the two had broken up (via CNN). Before long, the exes were out and about in the media, coughing up tidbits about what might have transpired. Timberlake's reaction was particularly intense, manifested through snarky statements in the press. Speaking to ABC's Barbara Walters, the singer refused to comment on the reason behind the breakup — only saying, "I don't judge anybody" — before going on to croon an unreleased track called "Horrible Woman." A piece in Betches observes that his Walters interview especially played up the "victim narrative" being spun around JT amid blazing rumors that Spears had been unfaithful to him. 

Spears, for her part, came out to say, "His priorities are different from mine right now" (per People). But she was soon compelled to address the cheating rumors in her ill-famed interview with Diane Sawyer in 2003. "I think everyone has a side of their story ... I'm not technically saying he's wrong, but I'm not technically saying he's right either," the pop queen said. In a deleted Instagram post from 2021, Spears recalled how after the breakup, she "couldn't talk" for a long time, simultaneously calling Sawyer out for her "'you're in the wrong' approach" and making her cry (via Harper's Bazaar). 

To say that Justin Timberlake and Britney Spears' breakup was a bad one would be an understatement. It was an absolute mess, with explosive public statements thrown into the mix, most notably by Timberlake, who is remembered for notoriously publicizing intimate details about his relationship in the media. For context, at the time, Spears had famously proclaimed that she was saving herself for marriage, as noted by The Guardian. Not long after their bitter split, Timberlake appeared on a radio show where he was asked in no uncertain terms if he and Spears ever did the deed, as per Slate. "Oh man. OK, I did it!" he revealed, a disclosure that reportedly led to malicious headlines directed at Spears. He allegedly made similar insinuations on ABC's "20/20" with Barbara Walters, laughing when asked if they had honored Spears' oath (via Friday Things). 

A similar invasive line of questioning followed Spears when she sat down with Diane Sawyer in 2003, for the now-infamous interview that left her crying. The host took a controversial tone while asking her about her sex life and more (via Glamour). Spears addressed the sensational gossip in a cover story for W Magazine that year, saying that she slept with Timberlake two years into their relationship. "I thought he was the one. But I was wrong! I didn't think he was gonna go on Barbara Walters and sell me out," she said (via EW). 

Music became an outlet for Justin Timberlake after his sour split from Britney Spears in 2002, resulting in one of his most successful numbers: "Cry Me A River." The breakup anthem was featured on his debut solo album, released that same year, and was famously inspired by the heartbreak he had incurred. The official music video for the song seemingly alluded to the circumstances surrounding Timberlake's breakup, and even featured a Spears lookalike. Francis Lawrence, music director for the song, however, told Dazed that there was an "unspoken agreement" not to explicitly discuss the identity of the muse, even on set (though one would be a fool not to know who the song was about). 

Timberlake wrote his revenge ballad in two hours, he revealed in his 2018 book "Hindsight." As quoted by People, he wrote, "I've been scorned. ... The feelings I had were so strong that I had to write it." 

When asked about the song, Spears, in a tell-all interview with Rolling Stone in 2011, said, "I think guys have egos, and when their egos get hurt and their pride's messed up, they deal in weird ways." She claimed Timberlake had called her up prior to the video's release, to let her know she was in it. Spears allegedly responded with her own musical release in 2003: "Everytime." Per PopSugar, the song supposedly reflected on the cheating allegations that broke the relationship.

Britney Spears and Justin Timberlake's split in 2002 sure did leave a lot of mess in its wake. Everything that transpired during that volatile period was swept under the carpet, and, in the years that followed, pop culture's reigning ex-couple gradually moved on from the fallout. Spears got married twice in 2004 – first to Jason Alexander, whom she divorced immediately, and then to Kevin Federline, with whom she had her two children. JT, meanwhile, married actor Jessica Biel in 2012 and shares two sons with her (via Brides). Spears and Timberlake near-about seemed to have disappeared from each others' lives; in 2007, Timberlake told Oprah Winfrey that he hadn't spoken to his ex in years, but that she was "a great person." 

If not romantically, the duo continued to hold each other in high praise musically. Much to the unanimous surprise of fans, there was some hint of a public reconciliation when the "Toxic" singer said that her former beau featured on her list of dream collaborators during a Q&A in 2016. "He's very good," Spears said. Per E! News, when informed of this development, Timberlake responded in the affirmative, saying, "I'm accessible, give us a call!" In fact, in 2018, buzz sparked of a possible collaboration between the ex-lovers, after rapper Timbaland gave a nudge-and-wink response when the subject was brought up on a podcast (via Business Standard). 

A collective gasp echoed across the world in April 2020 when Britney Spears took to Instagram to share a dance video of herself. The video itself was not unusual, given the 40-year-old's candid social media spirit — but what made heads spin was the accompanying caption. In it, Spears had casually addressed her infamous two-decade-old breakup with Justin Timberlake, even dropping him a compliment (via People). Shaking a leg to Timberlake's 2018 song "Filthy," Spears wrote, "PS I know we had one of the world's biggest breakups 20 years ago.... but hey the man is a genius!!!! Great song JT!!!!!" The post reached the man himself, who responded to it publicly, sending Y2K fandoms into a tizzy. Per Complex, Timberlake left a series of emojis — including a laughing smiley and some raised hands — on Spears' video, which since appears to have been removed. 

Following this viral moment, a source told HollywoodLife that while the two singers weren't exactly the best of friends, "they have no issues with each other," confirming that they haven't lost touch over the years. As far back as 2006, four years fresh from the breakup, Timberlake had spoken fondly about rooting for his ex: "I wish her well, and I want to see her win," he told GQ, per reports. On Oprah, a year later, he said Spears had a "huge heart" and that he had "nothing but love for her." 

The levee broke when "Framing Britney Spears," a documentary on the pop singer's life, was released in 2021. It brought to the fore the lifelong struggles Spears had faced, right from her troubled days as a showbiz star to the present time when she was fighting to have her legal conservatorship ended (via the BBC). A key aspect touched upon was the treatment Spears was subjected to in the media, per The New York Times (which produced the film), with a spotlight on her most high-profile ex Justin Timberlake's conduct following their breakup in 2002. As noted by CNN, after the film surfaced, a wave of anger directed towards Timberlake imploded on the internet, most notably for the sexual details he spilled about their relationship at the time. 

Calls abounded for the "SexyBack" singer to issue an apology, at the very least. They did not go unheard, eliciting a statement from Timberlake on Instagram. Recognizing how he "benefited from a system that condones misogyny and racism," the 41-year-old wrote, "I specifically want to apologize to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed." In relation to Jackson, criticism has hounded Timberlake since the 2004 Super Bowl halftime show when he accidentally exposed her breast. Following Timberlake's 2021 statement, Jackson addressed the controversy, saying, "He and I have moved on, and it's time for everyone else to do the same."

Britney Spears' 1999 debut music album, "...Baby One More Time," was enough to cement her as the pop queen of her generation. This status she held remained untarnished even in the face of snarky headlines and intrusive controversies that put her love life under high-glare. In 2007, especially, Spears was the object of intense media scrutiny owing to what is infamously recalled as a meltdown, which involved Spears shaving her head, being admitted to a psychiatric hospital, and fighting a custody battle for her children (via CBS News). In the wake of these issues, the then 26-year-old singer's father Jamie Spears was legally granted conservatorship, i.e. control, over her life and assets (per the BBC).

As indicated by The New York Times, which also produced the documentary "Framing Britney Spears" that focused attention on her struggle, Spears found the conservatorship "oppressive" and had been pursuing freedom for years. "I just want my life back," she reportedly told a court in June 2021. Amid the wave of online support pushing the #FreeBritney movement was the singer's ex-beau Justin Timberlake, who wrote on Twitter: "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 one should EVER be held against their will." The conservatorship was finally dissolved in November 2021 (via The Washington Post). 

For Britney Spears, Instagram appears to be a major platform for plainspeak — and by plainspeak, we mean really plain! The Princess of Pop doesn't rein herself in when looking back at her tumultuous past, often dropping casual truth bombs about the good, bad, and ugly. Her ex-boyfriend Justin Timberlake has featured in these flashbacks more than once. In a post from September 2021, Spears threw it all the way back to the 2001 Video Music Awards — yes, to that iconic performance she gave with a live tiger and python (via MTV). Spears recalled feeling (understandably) anxious with having to be locked in a cage with a wild beast, but also remembered how Timberlake "held my hand and gave me a 5 minute pep talk which obviously worked." 

Notwithstanding the odd praise for Timberlake, Spears also hasn't held back on criticism for the "Suit & Tie" singer. Page Six reported that in March 2022, Spears shared an Instagram post accusing her mother, sister, and an unnamed ex of allegedly using her. Of the latter, she wrote "he served with his first album using your name claiming you did him dirty !!!!" referencing Timberlake's debut album "Justified," which was famously inspired by his breakup with Spears in 2002 (via CNN). Any confusion about the identity of said ex was laid to rest with a picture of Timberlake in Spears' post, which was later deleted.