There may be no relationship that epitomized both the allure and the toxicity of early-aughts celebrity culture as much as the three-year relationship of Britney Spears and Justin Timberlake. The power pairing of the pop princess and the boy-band member turned solo crooner was a fairy-tale romance for the 2000s—until a messy and highly publicized breakup shattered the illusion, leading to more than two decades of tabloid fodder and speculation.
For Timberlake, the high-profile relationship boosted his celebrity, especially following their split; the singer and actor parlayed the media frenzy surrounding their breakup into promotion for his first solo album, including a music video, where he implies that Spears cheated on him. Spears, on the other hand, has suffered criticism for years, due, at least in part, to Timberlake’s framing of their breakup and the ensuing sexist and insensitive media narratives that emerged. For both parties, the relationship, however brief, has become an integral part of their cultural legacies, shaping how we see them both as a former couple and stars in their own right
In recent years, the narratives surrounding Spears and Timberlake have begun to be reframed. A reckoning with Y2K tabloid culture, misogynistic media narratives about women during that time, and particularly the relentless and often cruel scrutiny that Spears suffered as a result of her time in the spotlight have all called for a new understanding of their relationship. Now, a revealing new memoir by Spears, The Woman in Me, which releases on Oct. 24, offers even more insight into one of pop culture’s most notorious relationships.
Here, a look back at Spears and Timberlake’s relationship—from when they met as child performers in the ’90s to where they stand now.
December 1992: Britney and Justin meet while starring in The All-New Mickey Mouse Club
Spears and Timberlake met for the first time as 11-year-olds in 1992, after they were both cast as “Mouseketeers” in the Disney variety TV show, The All-New Mickey Mouse Club. The show, which was the third revival of the 1950s show, The Mickey Mouse Club, was a hub for young performers who would go on to achieve superstardom; Spears and Timberlake’s colleagues on the show included actors Ryan Gosling and Keri Russell, pop star Christina Aguilera, and Timberlake’s fellow NSYNC member, JC Chasez.
In her memoir, Spears describes the show as “boot camp for the entertainment industry,” with dance rehearsals where they would run choreography 30 times in a day, singing and acting classes, recording studio sessions, and school. According to Spears’ recollection, she and Timberlake connected quickly and he was even her first kiss.
“[Once] at a sleepover, we played Truth or Dare, and someone dared Justin to kiss me,” she writes in The Woman in Me, a copy of which was obtained by TIME ahead of its publication. “A Janet Jackson song was playing in the background as he leaned in and kissed me.”
For Timberlake, the connection with Spears even at a young age was undeniable. “I was in love with her from the start,” he told GQ in a 2006 interview. “I was infatuated with her from the moment I saw her.”
1999: Britney and Justin begin secretly dating
Spears and Timberlake reunited in November 1998, when Spears joined NSYNC as the opening act for the second leg of their NSYNC In Concert Tour, ahead of the 1999 release of her debut album, …Baby One More Time. After Spears began touring with the band, rumors swirled that she was dating Timberlake, but Spears denied the speculation in an April 1999 interview with Rolling Stone.
“Overseas they say it’s Nick Carter of Backstreet Boys,” she said of gossip that she was dating Timberlake or another boy bander, Lance Bass. “I have no feelings at all.”
In a later interview, however, Spears revealed that Timberlake had asked her out in 1999 on tour, ahead of her album’s release.
“He definitely asked me out,” she told television broadcaster Andi Peters in a 2001 interview ahead of the Teen Choice Awards. “We were doing a radio show, and this was before …Baby One More Time came out … He knocks on the door and he was like, ‘Can I see Britney?’ And [my assistant] Felicia [Culotta] didn’t know who he was and she was like, ‘No … Who are you?’ And I was like, ‘No! It’s Justin!’”
September 2000: Britney and Justin make their first public appearance as a couple
Spears and Timberlake made their public debut as a couple at the 2000 MTV Video Music Awards. While the pair didn’t walk the red carpet together, opting instead for Timberlake to walk with his NSYNC bandmates and Spears solo, the couple sat together during the show.
January 2001: Britney and Justin make their first red-carpet appearance as a couple
Perhaps no other image has defined Spears and Timberlake’s relationship as much as their matching all-denim looks for the 2001 American Music Awards red carpet. According to fashion designer Steven Gerstein, the matching denim ensembles were the couple’s idea.
“Justin and Britney were dating at the time. We were in New Orleans when Britney and Justin were like, ‘We’re doing matching denim.’ And I was like, ‘How are you doing that? Who is doing that?’” Gerstein told Jezebel in a 2020 interview about the looks. “Obviously, the Britney/Justin connection added fuel to the fire, but it was really organic…it was just two kids, wanting to do something cool, and being super cute, matching. It was kind of like their prom.”
In her memoir, Spears shares that she drew inspiration for the denim outfits from Southern mothers who color-coordinated their children’s church outfits and has been pleased with how it’s been immortalized as a part of early-aughts pop culture.
“I get that it was tacky, but it was also pretty great in its way, and I am always happy to see it parodied as a Halloween costume,” she writes. “I’ve heard Justin get flak for the look. On one podcast where they were teasing him about it, he said, ‘You do a lot of things when you’re young and in love.’ And that’s exactly right. We were giddy, and those outfits reflected that.”
January 2001: Britney and Justin perform together at the Super Bowl XXXV halftime show
Spears and Timberlake shared the stage for the Super Bowl halftime show, where NSYNC was headlining with Aerosmith. Spears appeared for a performance of “Walk This Way,” along with Nelly and Mary J. Blige. Spears’ appearance helped to increase buzz around the couple’s relationship.
“It’s a little hard, but you know what, it’s all about trust,” she told Entertainment Tonight in a backstage interview ahead of the show. “He loves me and I love him and we just try to work it out.”
July 2001: Britney and Justin reveal their nicknames for one another
Spears and Timberlake revealed their silly nicknames for one another at an unlikely place: a charity event hosted by NSYNC. At “Challenge for the Children,” a July 2001 charity basketball competition that Timberlake co-hosted with his bandmates, the couple wore matching jerseys that had their nicknames for one another (“Pinky” for Spears and “Stinky” for Timberlake) emblazoned on the back. In a later interview, Spears revealed the origin of their nicknames.
“I have a ring that he gave me that I wear on my pinky so he started calling me Pinky, and then I started calling him Stinky for some reason, so that’s our nicknames,” Spears told Oprah in February 2002.
September 2001: Justin supports Britney ahead of her 2001 MTV Video Music Awards performance
Although it’s hailed as one of her most iconic performances, Britney’s 2001 VMAs performance, where she danced with an albino Burmese python wrapped around her shoulders, was one of the acts that terrified her the most.
