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

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

Timberlake and Spears known as it quits 20 years ago, but lovers are nonetheless invested in their rocky romance. The former boy bander and pop princess met within 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 in the past. But it is a deeper love now than when I used to be younger,” Spears gushed to The Observer in 2001. “Like, we’ve long gone through so much in combination and we’ve recognized each and every different since we had been 12 years old. We know each other within and out.”

While the twosome steadily gushed about each and every other — and infamously rocked matching denim outfits at the 2001 American Music Awards — their relationship got here to an lead to early 2002. Their break up temporarily became messy after Timberlake released his song, “Cry Me a River,” and spread out about their dating to Barbara Walters.

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“Sure,” Timberlake sarcastically replied during the 20/20 interview when asked whether or not Spears, who in the past said she planned to wait to have sex until marriage, nonetheless had “just right morals.”

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

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