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.
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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 October 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.
Read More: Britney Spears Feared Her Family Would Kill Her, She Writes in New Book
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 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.”
Read More: Britney Spears Details Her 55-Hour Marriage to Jason Alexander
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.
“It’s become an iconic moment in VMAs history, but it was even more terrifying than it appeared,” she writes of the moment in her new memoir. “All I knew was to look down, because I felt if I looked up and caught its eye, it would kill me.”
Spears shared on Instagram in 2021 that Timberlake helped to calm her nerves before the performance. In the caption to the post, she wrote: “Justin saw I could hardly talk so he held my hand and gave me a 5 minute pep talk which obviously worked.”
September 2001: Britney reveals she and Justin are living together
In an interview with The Guardian, Spears shared that when Timberlake was in L.A., he lived with her at her house. She also opened up about how their relationship evolved over the two years they had been dating.
“I’m not ashamed at all to say that I love him from the bottom of my heart,” she told them. “As far as love is concerned, with him, too much is not enough. He’s everything…but 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.”
November 2001: Justin writes and produces a song on Britney’s album, Britney
For Spears’ third studio album, Timberlake wrote and produced the song “What It’s Like to Be Me,” alongside Spears’ backup dancer, the choreographer, Wade Robson; Timberlake also contributed background vocals.
“I have to say I was a little nervous at first,” she said in an interview with MTV. “But then I just totally forgot that he was my boyfriend, and I just said, ‘Britney, just do the vocals, don’t be nervous’ … But it ended up being fine, actually.”
February 2002: Justin makes a cameo in Britney’s Saturday Night Live opening monologue
When Spears did her second stint as the host and musical guest on SNL, Timberlake made a surprise appearance during her opening monologue. His guest turn fanned rumors that the couple were getting engaged, which she debunked in a post-show interview with Katie Couric, as reported by People. When asked if there was “any news on the Justin front,” she had a succinct answer: “No.”
Spring 2002: Britney and Justin live together in Orlando
In her memoir, Spears also reveals that by the spring of 2002, she and Justin also lived together in a house in Orlando, which they treated as their “home base.”
“In my personal life, I was so happy,” she writes. “Justin and I lived together in Orlando. We shared a gorgeous, airy two-story house with a tile roof and a swimming pool out back. Even though we were both working a lot, we’d make time to be home together as often as we could. I always came back every few months so Justin and I could be together for two weeks, sometimes even two months at a time.”
Spears also shares in the memoir that she was “smitten” with Timberlake during this time.
“I don’t know if when you’re younger, love’s a different thing, but what Justin and I had was special. He wouldn’t even have to say anything or do anything for me to feel close to him.”
February 2002: Britney and Justin make their final red-carpet appearances together
In early February 2002, Spears and Timberlake walked the red carpet for the Los Angeles premiere of her film, Crossroads, where she made her silver-screen debut. The film’s director, Tamra Davis, said that Timberlake was a regular presence on the set to support Spears, who would doodle their names together in her notebook.
“I have the book. All she was writing was ‘Britney and Justin,’ all these little curlicues,” Davis said in a 2016 interview with Vice. “It was like looking at a teenage girl’s musings—hearts and butterflies and Justin’s name.”
Later that month, the pair appeared together at Clive Davis’ pre-Grammys party, one of their final red-carpet public appearances together.
March 2002: Britney confirms breakup with Justin after three years together
Spears seemingly confirmed the couple’s breakup during her press tour for Crossroads. According to a report by Entertainment Weekly at the time, Spears told reporters during a press conference in London that she was “not in an intense relationship with anyone at the moment.” Later that week, during an appearance on the Big Breakfast talk show, she reiterated her single status: “I’m single… right now.”
Read More: What Rewatching Crossroads Reveals About Britney Spears
In her memoir, Spears alleges that Timberlake initiated the breakup while he was making his first solo album, Justified, because he wanted use her “as ammunition for his record.” Spears also writes that he broke up with her via text message while she was shooting her music video for a remix of “Overprotected.” While he later visited her at her family’s home in Louisiana to dissolve their relationship in person, bringing her a letter that he wrote and framed (that Spears says she still has under her bed), the breakup was still devastating, with Spears noting that she cried and could barely speak for months, leading her to wonder if she was “clinically in shock.” Timberlake has not commented on Spears’ memoir.
November 2022: Justin addresses their breakup during his media tour for his solo album
Ahead of the release of his first solo album, much of the media around Timberlake focused on his split from Spears. In an interview with People, Timberlake talked about his “broken heart.”
“It hurts too bad,” he said. “You get to a point when you’re crying yourself to sleep every night. I feel like I’m in the middle of a soap opera.”
In a 20/20 interview with Barbara Walters, Timberlake avoided speaking about why they broke up: “Honestly, I mean, you know, we’re not perfect. I don’t judge anybody. It’s just young love…It was a very intense relationship, that’s for sure.”
November 2022: Justin’s music video for “Cry Me a River” sparks rumors that Spears cheated on him
Timberlake’s second single from Justified, “Cry Me a River,” dealt with themes of infidelity, which were echoed in the music video for the song featuring a Spears look-alike.
In her memoir, Spears writes that in the time following the release of the “Cry Me a River” music video, she suffered from awful scrutiny from the news media and from fans, who assumed that the narratives around being cheated on were inspired by her.
“In the news media, I was described as a harlot who’d broken the heart of America’s golden boy,” she writes. “The truth: I was comatose in Louisiana, and he was happily running around Hollywood.”
She recalls being booed everywhere she went, from clubs to a Lakers game, where the whole arena booed her. For Spears, the shaming she suffered was especially painful because of his own infidelity. While Spears had cheated on Timberlake just once—making out with her backup dancer Wade Robson—she alleges that he cheated on her several times.
“There were a couple of times during our relationship when I knew Justin had cheated on me,” she writes. “Especially because I was so infatuated and so in love, I let it go.”
November 2003: Britney speaks about the breakup with Diane Sawyer
In a now-infamous episode of Primetime, Diane Sawyer asked Spears about the breakup in a manner that many now consider insensitive.
“He’s going on television and pretty much said you broke his heart. You did something that caused him so much pain, so much suffering. What did you do?” Sawyer asked, before pressing Spears on whether she had cheated on Timberlake. “He left the impression that you weren’t faithful, that you betrayed the relationship.”
Spears, for her part, responded neutrally. “I think everyone has a side of their story to make them feel a certain way,” she said. “I’m not technically saying he’s wrong, but I’m not technically saying he’s right either.”
May 2004: Spears releases the music video for “Everytime,” which some fans interpret as a response to “Call Me a River”
In May 2004, Spears released the music video for her song, “Everytime,” which portrays the end of a high-profile relationship, leading many fans to speculate that it was about her split with Timberlake. Spears says the song, which includes the lyrics: “I may have made it rain / Please, forgive me / My weakness caused you pain / And this song’s my sorry,” is about the heartbreak of losing your first love.
“It’s about heartbreak, it’s about your first love, your first true love,” she told MTV in a 2004 interview. “That’s something all people can relate to, because you all have that first love that you think you’re going to be with the rest of your life.”
Since Spears revealed in her new memoir that she had an abortion while dating Timberlake, fans have been speculating that the song is actually about feelings around terminating her pregnancy, pointing to a scene in a hospital where one woman is dying, while another gives birth.
July 2006: Justin blames Britney for breakup fallout
In an interview with GQ in 2006, Timberlake slammed Spears for how she handled their split publicly, saying that he wrote “Cry Me a River” in two hours as a response.
“I felt like she had a couple of opportunities to just sort of stick up for me, and she didn’t,” he said. “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.”
February 2021: Justin issues a public apology to Britney
Two decades after they first began dating, Timberlake released a public apology on social media to Spears, after facing criticism following the release of Framing Britney Spears, a New York Times documentary that reviewed how the media and relentless scrutiny negatively impacted Spear’s personal, public, and business lives. Timberlake also used his statement to apologize to Janet Jackson for the racist and misogynistic narratives and treatment she was subject to after he exposed her breast during the 2004 Super Bowl halftime show.
“I’ve seen the messages, tags, comments, and concerns and I want to respond. 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 for what was right,” Timberlake wrote. “I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism,” he continued. “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…I have not been perfect in navigating all of this throughout my career. I know this apology is a first step and doesn’t absolve the past. I want to take accountability for my own missteps in all of this.”
October 2023: Britney reveals that she had an abortion while she was dating Timberlake
In The Woman in Me, Spears reveals that she had a medical abortion during her relationship with Timberlake.
“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,” Spears writes of finding out she was pregnant. “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. 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.”