Britney Spears and Justin Timberlake's Relationship: A Look Back

Britney Spears and Justin Timberlake dated from 1999 to 2002

In the early 2000s, Britney Spears and Justin Timberlake seemed to be a modern-day fairy tale.

After first crossing paths as preteens on the set of The 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.

When the pair began dating in 1999, their young love story was a constant subject of public fascination and became even more so when they split in spring 2002. Following their public breakup, the scrutiny of the former couple only intensified, with Timberlake penning revenge music.

In 2007, however, Timberlake told Oprah 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 dancing to her ex's music on social media.

Related: A Look Back at Justin Timberlake & Britney Spears' Relationship in Photos

Here is a look back at Britney Spears and Justin Timberlake's relationship.

December 1992: Britney Spears and Justin Timberlake meet while filming The All-New Mickey Mouse Club

Spears and Timberlake first met when they were cast in the '90s revival of The Mickey Mouse Club, along with future stars JC Chasez, Ryan Gosling and Christina Aguilera. Though they were both just 11 years old at the time, the young performers had an instant connection — and Timberlake 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. A Janet Jackson song was playing in the background as he leaned in and kissed me," she wrote.

Spears had equally fond memories of the Mickey Mouse Club set. "It was a really 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 to Rolling Stone.

"Overseas, they say it's Nick Carter of the Backstreet Boys," she told the outlet. "I have no feelings at all."

But Spears would later reveal Timberlake asked her out prior to the release of her debut album in January 1999.

"He definitely asked me out. 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!' " Spears later recalled in a interview with Andi Peters.

September 7, 2000: Britney Spears and Justin Timberlake take their relationship public

After denying romance rumors for months, Spears and Timberlake made their debut as a couple at the 2000 MTV Video Music Awards. Though they walked the red carpet separately — Timberlake with *NSYNC and Spears solo — the pair sat together during the show and were openly cuddling and affectionate.

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" and The 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

At the 2001 American Music Awards, Spears and Timberlake hit the red carpet in their now-infamous matching 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 also recalled the denim-on-denim look 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

Spears and Timberlake, as part of *NSYNC, performed together at the Super Bowl halftime show, alongside Aerosmith, Nelly and Mary J. Blige. *NSYNC and Aerosmith headlined, performing hits like "Bye Bye Bye" and "I Don't Want to Miss a Thing," and were later joined by Spears, Blige and Nelly for a rendition of "Walk This Way."

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 told Entertainment 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 supported Timberlake during *NSYNC's third annual Challenge for the Children charity event, as reported by Billboard. The charity event concluded with a celebrity basketball game, where Spears and Timberlake wore matching jerseys featuring their nicknames for each other: Pinky and Stinky.

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 to Billboard.

September 6, 2001: Justin Timberlake calms Britney Spears' nerves before VMAs performance

Spears' performance of "I'm a Slave 4 U" at the 2001 MTV Video Music Awards involved several live exotic animals — including a tiger that accompanied her entrance and a 7-foot albino Burmese python draped over her shoulders. Though Spears didn't appear rattled during the performance, she later revealed that Timberlake had to give her a "pep talk" to calm her nerves before she took the stage that evening.

"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

In an interview with The 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

Spears and Timberlake collaborated on the song "What It's Like to Be Me" from her third album, Britney. Timberlake and Wade Robson, one of Spears' backup dancers, wrote and produced the song, and Timberlake contributed background vocals. Though they'd performed together before, Spears revealed to MTV that she was "nervous" to work with her boyfriend.

"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."

Spears also clarified in a press conference that the lyrics of the song were not about her, despite being written by her then-boyfriend. "It's talking about a girl in a relationship and the boy doesn't understand what she's going through. Before she opens up to him, he has to realize what she's about," she explained.

February 2, 2002: Justin Timberlake joins Britney Spears on Saturday Night Live

For Spears' second appearance on Saturday Night Live as 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 to Katie Couric about her time on SNL and 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 the Crossroads premiere

Timberlake joined Spears on the red carpet for the L.A. premiere of Spears' acting debut in Crossroads. According to director Tamra 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," Davis told Vice in 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

Spears and Timberlake hit the Grammys red carpet together in 2002 — one of their last red carpet appearances before splitting. At the ceremony, Spears presented the award for best pop performance by a group or duo. Timberlake was nominated in that category with *NSYNC — but Spears did not get the chance to present her boyfriend with a Grammy, as U2 won the category.

March 2002: Britney Spears says she's no longer in an "intense relationship" with Justin Timberlake

While promoting Crossroads in 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 friend Tara Reid in 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 album Justified, Timberlake sat down for an interview with 20/20's Barbara 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" on TRL, 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.

The lyrics, co-written by Timberlake, included: "Told me you loved me / Why did you leave me all alone? / Now you tell me you need me / When you call me on the phone."

In an interview with TRL's Carson 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 to The Boston Globe.

But Timberlake later opened up about writing "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."

August 2003: Britney Spears is disappointed by Justin Timberlake's music video

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 with Diane Sawyer on Primetime, 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

Spears and Timberlake eventually moved on to new relationships — Spears married Kevin Federline in September 2004 and Timberlake began dating actress Cameron Diaz in 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 the world's biggest breakups 20 years ago…. but hey the man is a genius!!!!" Spears wrote. "Great song JT!!!!!"

Timberlake commented on the post with a series of emojis: "😂🙌🏻🙌🏻🙌🏻."

February 12, 2021: Justin Timberlake publicly apologizes to Britney Spears

Timberlake posted a public apology on 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 and Janet Jackson both 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 he exposed Jackson's breast.)

He added: "I care deeply about the well-being of the people I love and have loved."

The apology came following the New York Times documentary Framing Britney Spears, which included Timberlake's former relationship with Spears. Specifically, the documentary questioned Timberlake's actions following the breakup, including "Cry Me a River" as a revenge song, its music video and Timberlake's public comments on his sex life with Spears.

June 23, 2021: Justin Timberlake supports Britney Spears during conservatorship hearing

Following Spears' court hearing to end the conservatorship she'd been under since 2008, Timberlake tweeted in support of his ex-girlfriend. At the hearing, Spears detailed that she was being forced to have an IUD to prevent her from having more children.

"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

In her 2023 memoir, The Woman in Me, Spears revealed that she got pregnant with Timberlake's baby during their three-year relationship but had an abortion.

“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 wrote of the pregnancy in her book, PEOPLE exclusively confirmed. “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."

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 on The Tonight Show Starring Jimmy Fallon on Instagram, Spears not only apologized to anyone she had "offended" in her memoir, The Woman in Me, but also mentioned 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.”

For more People news, make sure to sign up for our newsletter!

Read the original article on People.