- Britney Spears and Justin Timberlake were the entertainment industry’s hottest couple.
- Timberlake was inspired to write the breakup anthem “Cry Me a River” after their 2002 split.
- Spears has revealed in her new memoir that she had an abortion while dating Timberlake.
Britney Spears has looked back at her relationship with Justin Timberlake in her memoir “The Woman In Me.”
Here’s a refresher of their history, which began when they met as castmates on “The All New Mickey Mouse Club” in the early 1990s.
Thanks to their statuses as pop icons, they’ve made big revelations about each other over the years and will be connected forever.
December 1992: Britney Spears and Justin Timberlake met as cast members on “The All New Mickey Mouse Club.”
Disney
Timberlake and Spears began their individual tenures on “The All New Mickey Mouse Club” with the 1993 season, and were part of the show through 1994.
They first met in December 1992 when they were cast, People reported.
“I was in love with her from the start,” Timberlake told GQ in 2006. “I was infatuated with her from the moment I saw her.”
In her October 2023 memoir, Spears recalls their first kiss, which happened during this time period.
“At a sleepover, we played Truth or Dare, and someone dared Justin to kiss me,” she writes in an excerpt of “The Woman in Me” shared by People. “A Janet Jackson song was playing in the background as he leaned in and kissed me.”
“That was probably one of the most special times in my life,” Spears told Entertainment Tonight of being on the show in 2018.
1998: Spears and Timberlake reunited on tour.
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The former Mouseketeers reunited in 1998 when Spears opened up for Timberlake’s group NSYNC on the second leg of their NSYNC In Concert tour that ran from late 1998 to 1999.
Spears was supporting her debut single “…Baby One More Time” and her upcoming album of the same name, released in January 1999.
1999: Timberlake and Spears began dating but denied it in the press.
Denise Truscello/WireImage
Rumors began to swirl that Spears and Timberlake were dating in 1999, but she denied it in one of her first interviews with Rolling Stone.
“Overseas they say it’s Nick Carter of Backstreet Boys,” she said of dating rumors about her. “I have no feelings at all.”
In a 2001 interview with Andi Peters, though, Spears confessed that Timberlake asked her out while they were on tour in 1999 before her debut album was released.
September 7, 2000: The couple made their red carpet debut.
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A year later, the stars made their first public appearance as a couple at the MTV Video Music Awards in September 2000. The pair sat next to each other during the ceremony and were photographed being affectionate, all but confirming their relationship to the public.
January 8, 2001: Spears and Timberlake famously wore matching denim outfits at the American Music Awards.
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By 2001, Spears and Timberlake had no problem with the world knowing that they were together and famously wore matching denim looks to the 2001 American Music Awards.
Celebrity designer Steven Gerstein was responsible for both looks and told Jezebel about how they came together in 2020.
“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.’ And I was like, ‘How are you doing that? Who is doing that?'” Gerstein said.
Gerstein designed Timberlake’s suit with help from contacts at Levi’s and a seamstress. Spears was working with costume designers Kurt and Bart at the time.
“It’s so funny, I sometimes forget that I did it, and forget that it is so iconic, because on my timeline it was one of a million outfits I had to come up with. That one just got a lot more traction than the rest. Obviously, the Britney/Justin connection added fuel to the fire, but it was a really organic … it was just two kids, wanting to do something cool, and being super cute, matching. It was kind of like their prom,” said Gerstein.
January 28, 2001: The couple performed together during the Super Bowl halftime show.
Scott Gries/ImageDirect
Timberlake’s band, NSYNC, co-headlined the show with Aerosmith.
After performing some of their hits, the bands brought Spears, Nelly, and Mary J. Blige on stage with them to sing the Aerosmith hit “Walk This Way.”
July 29, 2001: Timberlake and Spears revealed their nicknames for each other to the world.
Kevin Mazur Archive 1/WireImage
Spears supported Timberlake at NSYNC’s “Challenge for the Children III” charity basketball event in July 2001.
The couple wore jerseys that complemented each other and memorably revealed to the world that their nicknames for each other were “Pinky” and “Stinky.”
“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 later revealed to Oprah Winfrey in 2002.
September 16, 2001: Spears revealed that the couple lived together.
AP Photo/Beth A. Keiser
In a September 2001 interview with The Guardian, Spears said that Timberlake lived at her house with her when he was in LA.
“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,” Spears, who was 19 at the time, said of Timberlake.
“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,” she continued.
Ten days before the interview was published, on September 6, 2001, Timberlake watched Spears perform her hit song “I’m A Slave 4 U” at the MTV VMAs, with exotic animals like a tiger during her entrance and a 7-foot albino Burmese python that she draped over her shoulders.
Reflecting on the performance on Instagram in 2021, Spears wrote that she panicked right before going on stage.
“Justin saw I could hardly talk so he held my hand and gave me a 5 minute pep talk which obviously worked,” she wrote.
February 2, 2002: Spears debunked engagement rumors after Timberlake made a cameo during her “Saturday Night Live” monologue.
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During Spears’ opening monologue on the sketch show, Timberlake showed up and made a surprise appearance.
While discussing her time on “SNL” — her second as both musical guest and host — with Katie Couric a few days later, per People, Spears stated that it was “fun” and she was less nervous than she had been the first time.
She also denied reports that she and Timberlake were engaged.
When asked if there was “any news on the Justin front,” she simply responded: “No.”
February 11, 2002: Timberlake and Spears made one of their last red carpet appearances before their breakup.
Vince Bucci/Getty Images
The couple were photographed holding hands and looking in good spirits at the Los Angeles premiere of Spears’ acting debut in the teen comedy-drama, “Crossroads.”
Director Tamra Davis told Vice in 2016 that Timberlake was by Spears’ side during the filming of the movie and that she sometimes caught Spears doodling hearts and scrawling “Britney and Justin” in a notebook in between takes.
The pair also walked the red carpet at Clive Davis’ pre-Grammys party on February 26, before Spears dropped the bombshell news that they had split up.
March 25, 2002: Spears confirmed that she and Timberlake had split up after three years together.
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Spears told reporters that she was “not in an intense relationship with anyone at the moment” during a press conference for “Crossroads” in London, reported Entertainment Weekly at the time.
Spears herself had previously denied the breakup in an MTV interview in early March, and so had her mom and her publicist just five days before she spoke out at the London press conference, per Entertainment Weekly’s report.
Two days later, when she appeared on the “Big Breakfast” show, she said: “I’m single… right now.”
November 4, 2002: Timberlake sat down for an interview with Barbara Walters and addressed the split.
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In the run-up to the release of his first solo album, “Justified,” Timberlake was asked repeatedly about the split.
In June, he told People that it had left him with a “broken heart,” and five months later he sat down with Barbara Walters for a “20/20” interview.
Timberlake avoided questions about why they had broken up, responding: “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 25, 2002: Timberlake released the music video for “Cry Me a River,” which led to speculation that Spears had cheated on him.
YouTube/Justin Timberlake
Just a few weeks after his conversation with Walters, Timberlake released the second single from his debut album, “Cry Me a River.”
Both the song’s lyrics and the music video — which featured a Spears lookalike — reference someone being unfaithful in a relationship.
“You don’t have to say, what you did / I already know, I found out from him,” Timberlake sings in the second verse.
In his 2018 memoir, Timberlake said that he penned the track in just two hours because he felt “scorned” and “pissed off.”
“I didn’t plan on writing it,” he wrote. “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.”
November 13, 2003: Britney spoke to Diane Sawyer about the breakup.
Allen Berezovsky / WireImage / Getty Images / Dia Dipasupil / Getty Images
“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 grilled Spears on an episode of “Primetime.”
“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 responded. “I will always love him, and he’ll always have a special place in my heart.”
“He left the impression that you weren’t faithful, that you betrayed the relationship,” Sawyer continued.
Spears responded: “I think everyone has a side of their story to make them feel a certain way. I’m not technically saying he’s wrong, but I’m not technically saying he’s right either.”
May 10, 2004: Spears released the music video for “Everytime,” which fans interpreted as a response to “Cry Me a River.”
YouTube/Britney Spears; Getty/Dave Hogan/Mission Pictures
The lyrics to the song include: “I may have made it rain / Please, forgive me / My weakness caused you pain / And this song’s my sorry.”
During an interview with MTV in 2004, Spears said: “It’s about heartbreak, it’s about your first love, your first true love. 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.”
However, in light of Spears’ revelation that she had an abortion while dating Timberlake, some of her fans have now theorized the song is actually about her regret over terminating the pregnancy.
July 25, 2006: Timberlake blamed Spears for the post-breakup media frenzy.
Getty Images/Staff
While promoting his 2006 album “FutureSex/LoveSounds,” Timberlake told GQ that “Cry Me a River” was indeed about Spears, and blamed Spears for how she handled the breakup.
“I felt like she had a couple of opportunities to just sort of stick up for me, and she didn’t. 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,” he said.
“FutureSex/LoveSounds” also featured “What Goes Around… Comes Around,” a song about karma that some critics interpreted to be about Spears and a sequel to “Cry Me a River.”
February 12, 2021: Timberlake issued a public apology to Spears after facing renewed scrutiny in the wake of “Framing Britney Spears.”
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Timberlake issued a public apology to Spears after receiving backlash following the release of The New York Times documentary “Framing Britney Spears,” which examined the toll fame and invasive media attention took on Spears’ life and career.
Timberlake also apologized to Janet Jackson for the treatment she faced after he inadvertently exposed Jackson’s 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.”
Timberlake went on to decry the music industry, which “sets men, especially white men, up for success,” and blamed his “ignorance” for allowing him to “benefit from others being pulled down.”
“I know this apology is a first step and doesn’t absolve the past,” Timberlake said, adding that he wanted to “take accountability” for his own “missteps.”
The singer concluded his statement by telling followers: “I can do better and I will do better.”
June 24, 2021: Timberlake publicly supported Spears during her court battle to end her conservatorship.
Matt Winkelmeyer/Getty Images, Alberto E. Rodriguez/Getty Images
The “Cry Me a River” singer was among the celebrities who voiced support for Spears after she testified about her life under legal constraints to a Los Angeles court in a bid to end her controversial conservatorship.
“After what we saw today, we should all be supporting Britney at this time. Regardless of our past, good and bad, and no matter how long ago it was… what’s happening to her is just not right,” Timberlake wrote on X (formerly Twitter). “No woman should ever be restricted from making decisions about her own body.”
In a series of follow-up posts, he said: “No one should EVER be held against their will… or ever have to ask permission to access everything they’ve worked so hard for.”
“Jess and I send our love, and our absolute support to Britney during this time. We hope the courts, and her family make this right and let her live however she wants to live,” Timberlake added.
October 17, 2023: Spears reveals in her memoir that she had an abortion while dating Timberlake.
Simon and Schuster
In an excerpt from “The Woman In Me,” the singer’s upcoming memoir, Spears says she had the abortion because Timberlake wasn’t ready for fatherhood.
“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 in “The Woman In Me,” per People.
“But Justin definitely wasn’t happy about the pregnancy,” she adds. “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.”
“To this day, it’s one of the most agonizing things I have ever experienced in my life,” she continues.
A representative for Timberlake did not immediately respond to Insider’s request for comment.