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Alexa, play “Cry Me a River” by Justin Timberlake — and then, cue up “Everytime” by Britney Spears.
Timberlake and Spears called it quits two decades ago, but fans are still invested in their rocky romance. The former boy bander and pop princess met in the early ’90s while filming The Mickey Mouse Club. In 1999, as their careers skyrocketed, Timberlake and Spears confirmed that they were dating.
“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,” Spears gushed to The Observer in 2001. “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.”
While the twosome often gushed about each other — and infamously rocked matching denim outfits at the 2001 American Music Awards — their relationship came to an end in early 2002. Their split quickly turned messy after Timberlake released his song, “Cry Me a River,” and opened up about their relationship to Barbara Walters.
“Sure,” Timberlake sarcastically replied during the 20/20 interview when asked whether Spears, who previously said she planned to wait to have sex until marriage, still had “good morals.”
Scroll through for a timeline of Spears and Timberlake’s ups and downs:
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1992
Spears and Timberlake were joined by Ryan Gosling, Christina Aguilera, Keri Russell and his future ‘NSync band member JC Chasez as cast members on The All-New Mickey Mouse Club in the early ‘90s.
“I was in love with her from the start,” he told GQ magazine in 2006. “I was infatuated with her from the moment I saw her.”
Credit: Shutterstock
1999
The twosome went public with their romance in 1999.
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2001
Timberlake and Spears walked several red carpets together and performed at the Super Bowl XXXV halftime show with Aerosmith, Nelly, Mary J. Blige and ‘NSync in 2001.
Credit: Shutterstock
2002
Timberlake and Spears split in 2002 and reports subsequently surfaced that she was unfaithful to him.
When asked about cheating rumors by Walters at the time, Timberlake said, “We’re not perfect. I don’t judge anybody. It’s just young love. It’s just young love. It was a very intense relationship, that’s for sure.”
During the same interview, Timberlake performed a song called “Horrible Woman,” which included the lyrics “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 momma.”
Credit: YouTube
2002
Timberlake’s “Cry Me a River” music video featured a Spears look-alike and recreated their split.
“I’ve been scorned. I’ve been pissed off. I wrote ‘Cry Me a River’ in two hours. I didn’t plan on writing it,” he recalled in his 2018 book, Hindsight: & All the Things I Can’t See in Front of Me, about the breakup track. “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. People heard me and they understood it because we’ve all been there.”
Credit: YouTube
2003
It’s been long speculated by fans that Spears wrote “Everytime” about Timberlake. “And every time I try to fly, I fall / Without my wings, I feel so small / I guess I need you, baby,” she sings. “And every time / I see you in my dreams / I see your face, you’re haunting me / I guess I need you, baby.”
Credit: YouTube
2003
Spears got visibly emotional while being questioned by Diana Sawyer regarding the split from Timberlake in 2003.
“You did something that caused him so much pain … so much suffering. What did you do?” Sawyer asked in the interview, which has come under fire after the release of 2021’s “Framing Britney Spears.”
“I was upset for a while. We both are really young and it was kind of waiting to happen. I will always love him … he is such a great person,” she replied.
When asked if she “betrayed” the relationship, Spears, who admitted she was shocked by the “Cry Me a River” video, replied, “I’m not technically saying he’s wrong, but I’m not technically saying he’s right either.”
Credit: GQ
2006
“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, which is fine. But at that time, you know, I fought back,” Timberlake told GQ in 2006.
Credit: Bei/Shutterstock
2011
Timberlake was often asked about Spears over the years, telling Vanity Fair in 2011 that they hadn’t spoken in “nine or ten years.”
“We were two birds of the feather — small-town kids, doing the same thing,” he told the magazine. “But then you become adults and the way you were as kids doesn’t make any sense. I won’t speak on her, but at least for me, I was a totally different person. I just don’t think we were normal; there was nothing normal about our existence.”
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2013
Before performing “Cry Me a River” in 2013, Timberlake told the crowd, “Sometimes in life, you think you found The One. But then one day you find out that she is just some bitch.”
He denied that he was speaking about Spears via Twitter at the time, tweeting, “OK. I see you. Wouldn’t disrespect ANYONE personally. Ever. #Relax #ItsBritneyBitch I do love that saying though *with accent* #Respect.”
Credit: Courtesy Britney Spears/Instagram
2020
Spears has been caught dancing to Timberlake’s music more than once over the years. In April 2020, she got ahead of the social media frenzy when she addressed their public split while dancing to his track “Filthy.”
“PS I know we had one of the world’s biggest breakups 20 years ago …… but hey the man is a genius,” she captioned the video. “Great song JT ✨ !!!! Pssss if you KNOW WHAT’S GOOD 😜 !!!!!!”
Timberlake replied with a series of emojis, “😂 🙌 🙌 🙌.”
Credit: Magnus Sundholm/Shutterstock; Eric Charbonneau/Sony Pictures/Shutterstock
2021
The Tennessee native, who married Jessica Biel in 2012, apologized to Spears — and Janet Jackson for the infamous 2004 Super Bowl incident — via Instagram after “Framing Britney Spears” dropped.
“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 up for what was right. I understand that I fell short in these moments and many others and benefited from a system that condones misogyny and racism,” he wrote in February 2021. “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 also feel compelled to respond, in part, because everyone involved deserves better and most importantly, because this is a larger conversation that I wholeheartedly want to be part of and grow from.”
After acknowledging that he was a man in a “privileged position” of power, Timberlake concluded, “I know this apology is a first step and doesn’t absolve the past. I want to take accountability for my missteps in all of this as well as be part of a world that uplifts and supports. I care deeply about the well-being of the people I love and have loved. I can do better and I will do better.”
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2021
Timberlake showed his support for Spears after she spoke out about her conservatorship for the first time in a June court hearing. “After what we saw today, we should all be supporting Britney at this time,” he tweeted. “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. No one should EVER be held against their will … or ever have to ask permission to access everything they’ve worked so hard for.”
The actor concluded, “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.”
Credit: Matt Baron/BEI/Shutterstock
January 2023
The “Circus” singer took to social media to reminisce about playing basketball alongside her old flame during a charity event.
“When we used to shoot hoops TOGETHER … that’s when miracles happened ✨ !!!” Spears captioned an Instagram post that featured photos of herself and Timberlake at the Challenge for the Children event in 2001. “I came out of my mom’s stomach just like we all did !!! Psss … why always cast me out ??? I’m equal as all !!!”
Credit: Kevin Mazur/WireImage
October 2023
In an early excerpt from Spears’ memoir, The Woman in Me, the singer recalled having an 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 wrote. “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 shared she decided to ultimately terminate the pregnancy because Timberlake wasn’t ready to be a father, but if it was solely up to her she “never would have done it.”
