A Rollercoaster Romance: Exploring the Complicated Love Story of Britney Spears and Justin Timberlake

Alexa, please play Justin Timberlake's "Cry Me a River" and then follow it with Britney Spears' "Everytime."

Despite their breakup two decades ago, Timberlake and Spears' tumultuous relationship continues to captivate fans. The former members of The Mickey Mouse Club first met in the early '90s. By 1999, when both of their careers were soaring, Timberlake and Spears publicly announced their relationship.

"It still feels the same with him as it did two years ago, but our love has grown deeper with time," Spears enthusiastically shared with The Observer in 2001. "We've been through so much together, and we've known each other since we were 12 years old. We understand each other completely."

While the couple often expressed their admiration for one another and famously made a fashion statement with their matching denim outfits at the 2001 American Music Awards, their relationship came to an end in early 2002. Their breakup quickly turned messy when Timberlake released his song, "Cry Me a River," and candidly discussed their relationship with Barbara Walters.

Scroll down to see a timeline highlighting the highs and lows of Spears and Timberlake's relationship.

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Britney Spears and Justin Timberlake: A Timeline of Their Ups and Downs

Alexa, play “Cry Me a River” by Justin Timberlake — and then, cue up “Everytime” by Britney Spears.

Timberlake and Spears ended their relationship twenty years ago, but their devoted fans still hold onto their tumultuous romance. The former member of a boy band and the pop princess first crossed paths in the early 1990s while working on The Mickey Mouse Club. In 1999, as their careers flourished, Timberlake and Spears publicly confirmed their romantic involvement.

"In my heart, my feelings for him remain unchanged after all these years. However, the love we share now is deeper than when we were younger," Spears enthusiastically expressed to The Observer in 2001. "We have been through so much together, having known each other since the age of twelve. We are fully acquainted with each other's true selves."

The twosome frequently praised each other, and gained attention for their coordinated denim outfits at the 2001 American Music Awards. However, their relationship came to an abrupt end in early 2002. The situation became complicated when Timberlake released his song, "Cry Me a River," and spoke openly about their relationship to Barbara Walters. When asked during the 20/20 interview if Spears, who had previously expressed her intention to abstain from sex until marriage, still maintained "good morals," Timberlake sarcastically responded with a "Sure."

Scroll through for a timeline of Spears and Timberlake’s ups and downs:

Credit: Bei/Shutterstock

Britney Spears and Justin Timberlake: A Timeline of Their Ups and Downs

Alexa, play "Cry Me a River" by Justin Timberlake, followed by "Everytime" by Britney Spears.

Though it has been twenty years since their split, fans continue to show a strong interest in the tumultuous relationship between Timberlake and Spears. The two first crossed paths in the early 1990s while working together on The Mickey Mouse Club. By 1999, their careers were on the rise and Timberlake and Spears made their relationship official.

"It's still the same with him as it was two years ago, but my love for him has grown deeper with time," Spears revealed in an interview with The Observer in 2001. "We have faced numerous challenges together and have known each other since we were just 12 years old. We have a complete understanding of each other."

Although the couple often expressed their admiration for one another, famously showcasing matching denim outfits at the 2001 American Music Awards, their relationship ultimately ended in early 2002. The aftermath of their breakup became messy when Timberlake released his song, "Cry Me a River," and spoke candidly about their relationship to Barbara Walters.

"Absolutely," Timberlake sarcastically quipped in response to the question about Spears' adherence to her previously stated intention of abstaining from sex until marriage, during the 20/20 interview.

Check out the following timeline outlining the various highs and lows in Spears and Timberlake's relationship:

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1992

In the early ‘90s, Spears and Timberlake, along with Ryan Gosling, Christina Aguilera, Keri Russell, and JC Chasez, who would later become a fellow 'NSync band member, joined The All-New Mickey Mouse Club as cast members.

"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 ended their relationship in 2002 amidst reports of her infidelity. When questioned about the cheating rumors by Walters, Timberlake replied, "We're all flawed. I don't pass judgment on anyone. It was just a case of young love. It was an incredibly passionate relationship, that's certain."

During the interview, Timberlake delivered a rendition of a track titled "Horrible Woman," which featured the following lyrical content: "Therefore, you were given an opportunity to become my significant other / I presume you sought a more clandestine arrangement / Moreover, you are aware that such behavior is unbecoming / Thus, let us forego the theatrics and simply contact your maternal figure."

Credit: YouTube

2002

Timberlake's music video for "Cry Me a River" showcased a look-alike of Spears and depicted their separation. In his book, "Hindsight: & All the Things I Can't See in Front of Me," he revealed that he wrote the song out of the intense emotions he experienced during their breakup. The song served as a way for him to express these feelings and connect with others who have gone through similar situations.

Credit: YouTube

2003

There has been extensive speculation among fans that Spears penned the song "Everytime" with Timberlake in mind. In the lyrics, she sings, "And every time I try to fly, I fall / Without my wings, I feel so small / I guess I need you, baby." She further adds, "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.

Sawyer questioned in the interview about the actions that inflicted profound pain and suffering upon him. She inquired, "What precisely did you do?" This particular interview has faced intense criticism following the distribution of the documentary "Framing Britney Spears" in 2021.

She responded, expressing her distress during a certain period. Given our youthful ages, it seemed inevitable for such a scenario to unfold. Regardless, my affection for him will endure eternally as he possesses incredible qualities," she conveyed.

When questioned about whether she "betrayed" the relationship, Spears, who was taken aback by the "Cry Me a River" video, responded, "I'm not explicitly stating that he is incorrect, but I'm not explicitly stating that he is correct either."

Credit: GQ

2006

"When we first went our separate ways, I felt that she had a few chances to support me, but she chose not to, which is okay. However, back then, I defended myself," Timberlake stated in a 2006 interview with GQ.

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2011

Timberlake has frequently been questioned about Spears over the years. In 2011, he conveyed to Vanity Fair that they had not communicated for "nine or ten years."

"We were like two birds of a feather - small-town kids, pursuing the same path," he shared with the magazine. "However, as we grew into adults, the way we were as children no longer seemed logical. I prefer not to comment on her, but speaking for myself, I had undergone a complete transformation. Our existence was anything but ordinary."

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2013

Prior to his performance of "Cry Me a River" in 2013, Timberlake addressed the audience, expressing the common experience of believing that someone is the perfect match for you, only to later realize that they are not the person you thought they were.

He refuted the claims that he was discussing Spears on Twitter at that moment, tweeting, "I acknowledge your presence. I would never personally show disrespect to ANYONE. Ever. #TakeItEasy #ItsBritneyBitch I do, however, appreciate that phrase *with an accent* #Respect."

Credit: Courtesy Britney Spears/Instagram

2020

Over the years, Spears has been glimpsed dancing to Timberlake's music multiple times. In April 2020, she proactively addressed their highly publicized breakup while showcasing her dance moves to his tune "Filthy."

"PS: I acknowledge that we had a significant breakup on a global scale two decades ago... Nevertheless, it cannot be denied that the man is exceptionally talented," she wrote in the video caption. "Fantastic song, JT!!!! Pssss, only if you truly understand what's genuinely commendable!!!!"

Timberlake responded with a sequence of emojis, " ."

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2021

Following the release of "Framing Britney Spears,"​​​ the individual from Tennessee, who tied the knot with Jessica Biel in 2012, issued an apology to not only Spears but also Janet Jackson for the notorious 2004 Super Bowl incident through Instagram.

"I have seen the messages, tags, comments, and concerns, and I feel the need to address them. I sincerely apologize for the times in my life where my actions have contributed to the problem, when I have spoken out of turn or failed to stand up for what is right. I understand that I have fallen short in these moments, as well as others, and have benefited from a system that promotes misogyny and racism," he stated in February 2021. "I want to personally apologize to Britney Spears and Janet Jackson, as I deeply care for and respect these women, and I acknowledge that I have failed them. Additionally, I feel compelled to respond because everyone involved deserves better, and most importantly, this is a broader conversation that I sincerely want to engage in and learn from."

After recognizing that he holds a privileged position of power as a man, Timberlake concluded, "I understand that this apology is just a starting point and does not erase the past. I am committed to holding myself accountable for my own mistakes and to actively contribute to a world that uplifts and supports others. The well-being of the people I love and have loved is of great importance to me. I am capable of improvement, and I am determined to do better."

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2021

Following Britney Spears' first public statement about her conservatorship in a court hearing in June, Timberlake expressed his support for her. In a tweet, he stated that everyone should stand by Britney during this time. He emphasized that regardless of their past, the current situation is unjust. Timberlake believed that no woman should be deprived of decision-making power over her own body and that no one should ever be forcefully held or have to seek permission for their hard-earned achievements.

The actor expressed his and Jess' love and unwavering support for Britney during this period. They fervently hope that the courts and her family will rectify the situation and allow her the freedom to live her life as she desires.

Credit: Matt Baron/BEI/Shutterstock

January 2023

The "Circus" singer took to social media to reflect on the time she played basketball with her former partner during a charitable event.

Reminiscing about the moment, Spears captioned an Instagram post with photos of herself and Timberlake at the Challenge for the Children event in 2001, saying, "When we used to shoot hoops TOGETHER...that's when miracles happened!!! I came into this world just like everyone else did from their mother's womb. Psss...why do I always get excluded? I'm equal to everyone else!!!"

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.

The pregnancy came as a surprise, although I didn't view it as a tragedy. My love for Justin was immense, and I had always envisioned us starting a family together in the future. However, this was happening sooner than I had expected," wrote Spears. "Unfortunately, Justin did not share my enthusiasm about the pregnancy. He believed that we were not prepared to have a child at this point in our lives and that we were too young."

Spears explained that she made the difficult decision to terminate the pregnancy because Timberlake was not ready to embrace fatherhood. However, if the choice had been solely hers, she stated that she would have never gone through with it.

In this article

Britney Spears

Justin Timberlake