Britney Spears, Justin Timberlake: a timeline of their ups and downs

Alexa, play 'Cry Me a River' by Justin Timberlake – and then put on “Everytime”. Britney Spears.

Timberlake and Spears called it quits 20 years ago, but fans are still invested in their rocky romance. The former boy bander and pop princess met while filming in the early 1990s The Mickey Mouse Club. In 1999, as their careers skyrocketed, Timberlake and Spears confirmed they were dating.

“With him it's still the same as I felt two years ago. But it's a deeper love now than when I was younger,” Spears said The observer in 2001. 'For example, we have been through so much together and we have known each other since we were twelve years old. We know each other inside and out.”

While the pair often gushed over each other — and infamously wore matching denim outfits at the 2001 American Music Awards — their relationship came to an end in early 2002. Their breakup quickly became messy after Timberlake released his song “Cry Me a River.” and opened up about their relationship with Barbara Walters.

“Sure,” Timberlake responded sarcastically during the 20/20 interview when asked if Spears, who previously said she planned to wait until marriage to have sex, still had “good morals.”

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