Alexa, play “Cry Me a River” by Justin Timberlake. Then, follow it up with “Everytime” by Britney Spears. The saga of Justin Timberlake and Britney Spears ended two decades ago, yet fans remain captivated by their tumultuous relationship. The two met in the early ’90s while filming The Mickey Mouse Club. By 1999, as their careers soared, Timberlake and Spears confirmed they were an item.
“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 told The Observer in 2001. “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.”
The couple often expressed their affection publicly and famously wore matching denim outfits at the 2001 American Music Awards. However, their relationship ended in early 2002. The breakup turned messy when Timberlake released “Cry Me a River” and discussed their relationship with Barbara Walters.
When asked if Spears, who had previously stated she would wait until marriage to have sex, still had “good morals,” Timberlake sarcastically replied, “Sure.”
Timberlake and Spears’ relationship timeline is filled with ups and downs. In the early ’90s, they were joined by Ryan Gosling, Christina Aguilera, Keri Russell, and JC Chasez on The All-New Mickey Mouse Club. “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.”
Their romance went public in 1999. By 2002, they had split, with rumors of infidelity swirling. Timberlake told Walters, “We’re not perfect. I don’t judge anybody. It’s just young love. It was a very intense relationship, that’s for sure.”
During the same interview, Timberlake performed “Horrible Woman,” a song with lyrics hinting at betrayal. The music video for “Cry Me a River” featured a Spears look-alike, further fueling speculation about their breakup. Timberlake later wrote in his 2018 book, Hindsight, “I’ve been scorned. I’ve been pissed off. I wrote ‘Cry Me a River’ in two hours. The feelings I had were so strong that I had to write it.”
Fans have long speculated that Spears’ song “Everytime” was about Timberlake. The lyrics, “And every time I try to fly, I fall / Without my wings, I feel so small / I guess I need you, baby,” seem to reflect her feelings post-breakup.
In 2003, Spears got emotional during an interview with Diana Sawyer about the split. “You did something that caused him so much pain … so much suffering. What did you do?” Sawyer asked. Spears replied, “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.”
Timberlake told GQ in 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.”
In 2011, Timberlake told Vanity Fair that he and Spears hadn’t spoken in “nine or ten years.” He said, “We were two birds of the feather — small-town kids, doing the same thing. But then you become adults and the way you were as kids doesn’t make any sense.”
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 later denied he was referring to Spears, tweeting, “OK. I see you. Wouldn’t disrespect ANYONE personally. Ever. #Relax #ItsBritneyBitch I do love that saying though *with accent* #Respect.”
Spears has been seen dancing to Timberlake’s music over the years. In April 2020, she addressed their public split while dancing to his track “Filthy.” She captioned the video, “PS I know we had one of the world’s biggest breakups 20 years ago …… but hey the man is a genius. Great song JT ✨ !!!! Pssss if you KNOW WHAT’S GOOD 😜 !!!!!!”
