Justin Timberlake and Britney Spears.Photo: Dave Hogan/Getty Images
In the early 2000s,Britney SpearsandJustin Timberlakeseemed to be a modern-day fairy tale.
After first crossing paths as preteens on the set ofThe Mickey Mouse Club, Spears and Timberlake later reunited in the late ’90s as they launched their pop star careers — Spears as a solo artist and Timberlake in the boy band*NSYNC.
In 2007, however, Timberlake toldOprah Winfrey, “There’s no ill will— I have nothing but love for her. She has a huge heart, and she is a great person.”
And in recent years,Spears has shared videos of her dancingto her ex’s music on social media.
Here is a look back at Britney Spears and Justin Timberlake’s relationship.
December 1992: Britney Spears and Justin Timberlake meet while filmingThe All-New Mickey Mouse Club
Britney Spears and Justin Timberlake in 2002.Ron Galella/Getty
Spears and Timberlake first met when they were cast in the ’90s revival ofThe Mickey Mouse Club, along with future starsJC Chasez,Ryan GoslingandChristina Aguilera. Though they were both just 11 years old at the time, the young performers had an instant connection — andTimberlake was even Spears' first kiss.
The pop star recalled the moment, which occurred at a sleepover with her castmates, in her 2023 memoir,The Woman in Me. “[Once] at a sleepover, we played Truth or Dare, and someone dared Justin to kiss me. AJanet Jacksonsong was playing in the background as he leaned in and kissed me," she wrote.
Spears had equally fond memories of theMickey Mouse Clubset. “It was areally good time,” she said in 2018. “It was a great time. It was probably one of the most special times in my life.”
Timberlake has also said of meeting Spears, “I was in love with her from the start. I was infatuated with her from the moment I saw her.”
1999: Britney Spears and Justin Timberlake begin dating
Spears and Timberlake reunited in late 1998 when she opened for *NSYNC on their *NSYNC in Concert tour — and they began fielding relationship questions almost immediately. In April 1999, Spears denied the rumors toRolling Stone.
“Overseas, they say it’sNick Carterof theBackstreet Boys,” she told the outlet. “I haveno feelings at all.”
But Spears would later reveal Timberlake asked her out prior to the release of her debut albumin January 1999.
September 7, 2000: Britney Spears and Justin Timberlake take their relationship public
Their confirmed romance wasn’t the only thing that set the world abuzz, though — Spears’iconic VMAs performance, featuring a mashup of “Oops!… I Did it Again” andThe Rolling Stones' “Satisfaction,” and her sparkling nude ensemble, were also hot topics.
January 8, 2001: Britney Spears and Justin Timberlake wear matching denim outfits on the red carpet
Jeffrey Mayer/WireImage
At the 2001 American Music Awards, Spears and Timberlake hit the red carpet in their now-infamousmatching denim ensembles. According to designer Steven Gerstein, the denim gown-and-suit combo was the couple’s idea.
“It was such a no-brainer. Justin and Britney were dating at the time. We were in New Orleans when Britney and Justin were like, ‘We’re doing matching denim,’ " Gerstein recalled in 2020. “It was kind of like their prom. They had an idea, and we did what they wanted as opposed to the other way around. The rest is history.”
Timberlake alsorecalled the denim-on-denimlook fondly. “You do a lot of things when you’re young and in love,” he said of their get-up.
January 28, 2001: Britney Spears and Justin Timberlake perform at the Super Bowl halftime show
Jeff Kravitz/FilmMagic
Backstage at the Super Bowl, Spears acknowledged her relationship with Timberlake. “It’s a little hard, but you know what, it’s all about trust,” she toldEntertainment Tonight. “He loves me and I love him and we just try to work it out.”
July 29, 2001: Britney Spears supports Justin Timberlake at *NSYNC charity event
Spears later told Oprah the origin of their pet names. “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!” she said, according toBillboard.
Justin Timberlake and Britney Spears.KMazur/WireImage
September 6, 2001: Justin Timberlake calms Britney Spears' nerves before VMAs performance
“I will tell you this … before I went on that night I was feeling kinda out of body with nerves,” she wrote on Instagram. “I mean … I was in a cage with a live lion 🦁😳 !!!!! 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 Spears reveals she is living with Justin Timberlake
Richard Corkery/NY Daily News Archive via Getty
In an interview withThe Guardian, Spears shared that her and Timberlake’s busy schedules often kept them apart — but when they were together, they lived at her house in L.A. Spears also opened up about their two-year relationship to the outlet, revealing that he still gave her butterflies.
“I’m 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,” she said.
She added: “With him, it’s still the same as I felt two years ago. 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 Timberlake writes and produces a song on Britney Spears' third album
“I have to say I was a little nervous at first,” Spears said. “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 2, 2002: Justin Timberlake joins Britney Spears onSaturday Night Live
Mary Ellen Matthews/NBCU Photo Bank/NBCUniversal via Getty
For Spears' second appearance onSaturday Night Liveas its host and musical guest, Timberlake made a cameo during her opening monologue. The episode also featured Chris Kattan dressed as a Spears impersonator.
A few days later, Spears talked toKatie Couricabout her time onSNLand her relationship with Timberlake. Spears shared that she was less nervous for her second time hosting and that it was “fun.” She also debunked engagement rumors.
“He’s doin' wonderful,” Spears said of Timberlake. But when asked if there was “any news on the Justin front,” she simply responded: “No.”
February 11, 2002: Justin Timberlake accompanies Britney Spears to theCrossroadspremiere
Timberlake joined Spears on the red carpet for the L.A. premiere of Spears' acting debut inCrossroads. According to directorTamra Davis, Timberlake was just as present during production.
“It was just the most beautiful relationship, seeing the two of them together and how love-y they were,” DavistoldVicein 2016. “They were just so close, and she was such a supporter of his. He worked just as hard as her. It was like, she would be doing rehearsals and he would be doing rehearsals. They really knew that life together.”
Davis also shared that Spears would doodle in a prop notebook on set. “I have the book. All she was writing was ‘Britney and Justin,’ all these little curlicues,” Davis recalled. “It was like looking at a teenage girl’s musings — hearts and butterflies and Justin’s name.”
February 27, 2002: Britney Spears and Justin Timberlake attend the Grammy Awards
Frank Micelotta/Getty
March 2002: Britney Spears says she’s no longer in an “intense relationship” with Justin Timberlake
While promotingCrossroadsin London, Spears said that she was “not in an intense relationship with anyone at the moment” — all but confirming her breakup with Timberlake.
The statement came after the couple had spent weeks denying rumors that they had split. Speculation of a breakup began when Spears was spotted crying with friendTara Reidin L.A., but the pop star quickly shot them down when speaking to the European press.
“No, that’s not true. Me and Justin did not split up,” Spears said earlier in March. Spears also shared that she and Timberlake did not get to spend much time together because of “work commitments.” (*NSYNC was on tour at the time.)
June 2002: Justin Timberlake says he has a “broken heart” over Britney Spears
Timberlake opened up to PEOPLE about life after his breakup with Spears. “It hurts too bad,” the singer shared. “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. I honestly know what it’s like to have a broken heart.”
Timberlake added: “I love Britney, and I’ll always love her.”
In July 2002, Spears said that the breakup was amicable and a result of conflicting schedules. “We’re climbing two different mountains,” she said. “Of course it’s gonna kind of hurt sometimes, and you wonder things. But you learn from it and grow. I’m trying to get to that point.”
November 2002: Justin Timberlake reflects on “young love” with Britney Spears
Before releasing his debut solo albumJustified, Timberlake sat down for an interview with20/20’sBarbara Walters— and spoke about his breakup with Spears.
Timberlake refused to comment directly on why they split, but he did offer an explanation about their relationship and its end: “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.”
Timberlake also shared a song called “Horrible Woman” that didn’t make the album’s final cut. While he denied the song was about Spears, the lyrics left fans thinking otherwise: “So you had your chance to be my lover / I guess you needed something more undercover / And you know that ain’t cool / So let’s skip the drama, call your mama.”
November 25, 2002: Justin Timberlake releases “Cry Me a River” music video with Britney Spears look-alike
Timberlake revealed the video for his single “Cry Me a River” onTRL, and the lyrics and storyline suggested that the song was about Spears. The video featured Timberlake catching a blonde actress (who donned low-rise jeans, a newsboy cap and a tattoo similar to Spears') cheating on him.
In an interview withTRL’sCarson Daly, Timberlake denied the Spears connection immediately. “A lot of people have asked if the video is about her. It’s not about her, it’s about me,” he said, according toThe Boston Globe.
But Timberlake later opened up aboutwriting “Cry Me a River"in his 2018 memoir.
“I’ve been scorned. I’ve been pissed off,” he wrote. “I wrote ‘Cry Me a River’ in two hours. I didn’t plan on writing it. The feelings I had were so strong that I had to write it, and I translated my feelings into a form where people could listen and, hopefully, relate to it.”
Denise Trusc / Getty
The next year, Spears opened up about Timberlake’s infamous music video.
“It was hard for me that he was so exploitative,” she said. “Every interview that he did, he was just talking about us in such an open way and I just felt, ‘Is nothing sacred anymore?’ It was weird. It was … disappointing.”
Reflecting on their relationship, Spears added: “I think I got way too serious, way too young. It’s very healthy to not be in that relationship right now.”
November 2003: Britney Spears talks about her breakup with Justin Timberlake to Diane Sawyer
In an interview withDiane SawyeronPrimetime, Spears faced a line of questioning that painted her as the cause of her split from Timberlake.
“You broke his heart. You did something that caused him so much pain, so much suffering. What did you do?” Sawyer asked Spears.
“I was upset. I was upset for a while … I think we were both really young and it was kind of waiting to happen,” Spears replied. “I will always love him and he’ll always have a special place in my heart.”
Sawyer pressed on and said, “He left the impression that you weren’t faithful, that you betrayed the relationship.”
Spears noted that Timberlake only shared his own perspective. “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. It was a really weird time … I just felt very exploited and very weird.”
July 2006: Justin Timberlake says he was “infatuated” with Britney Spears
KMazur/WireImage
Spears and Timberlake eventually moved on to new relationships — Spears marriedKevin Federlinein September 2004 and Timberlake began dating actressCameron Diazin 2003. In 2006, Timberlake reflected on his relationship with Spears. The *NSYNC alum shared that he was “infatuated” with Spears from the moment he saw her, but that their relationship was “so high school” and had become “a distant thing.”
Timberlake also touched on their 2002 split and his infamous breakup ballad. “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 said. “Which is fine. But at that time, you know, I fought back. I used my mind. I came up with a song.”
April 15, 2020: Britney Spears calls her split with Justin Timberlake one of the “world’s biggest breakups”
Years after their relationship ended, Spears posted an Instagram video of herself dancing on a balcony to Timberlake’s song “Filthy.” In the caption, Spears complimented her ex on his music and referenced their highly publicized split.
“I know we had one of theworld’s biggest breakups20 years ago…. but hey the man is a genius!!!!” Spears wrote. “Great song JT!!!!!”
Timberlakecommented on the postwith a series of emojis: “😂🙌🏻🙌🏻🙌🏻.”
February 12, 2021: Justin Timberlake publicly apologizes to Britney Spears
Timberlakeposted a public apologyon his Instagram for his behavior surrounding his breakup from Spears — in particular, for contributing to a system that “condones misogyny and racism.”
In the lengthy Instagram post, Timberlake wrote: “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 up for what was right. I understand that I fell short in these moments and in many others … I specifically want to apologize to Britney Spears andJanet Jacksonboth individually, because I care for and respect these women and I know I failed.” (Timberlake and Jackson were the center of controversy for their 2004 Super Bowl halftime performance, in which heexposed Jackson’s breast.)
He added: “I care deeply about the well-being of the people I love and have loved.”
June 23, 2021: Justin Timberlake supports Britney Spears during conservatorship hearing
“After what we saw today, we should all be supporting Britney at this time,” Timberlake said. “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 concluded his thread with a message on behalf of him and his wife,Jessica Biel. “Jess and I send our love, and our absolute support to Britney during this time,” he wrote. “We hope the courts, and her family make this right and let her live however she wants to live.”
October 17, 2023: Britney Spears reveals she had an abortion during relationship with Justin Timberlake
Spears continued, “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.”
January 29, 2024: Britney Spears says she’s “in love” with Justin Timberlake’s new single, “Selfish”
Sharing a video from Timberlake’s appearance onThe Tonight Show Starring Jimmy FallononInstagram, Spears not only apologized to anyone she had “offended” in her memoir,The Woman in Me,but alsomentioned her ex’s new music.
“I wanna apologize for some of the things I wrote about in my book. If I offended any of the people I genuinely care about I am deeply sorry…” Spears wrote in her caption. “I also wanted to say I am in love with Justin Timberlake’s new song ‘Selfish’ 🌹 It is soo good and how come every time I see Justin and Jimmy together I laugh so hard ??? Ps ‘Sanctified’ is wow 🤩 too.”
source: people.com
