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 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: