From double-denim red-carpet looks to revenge music videos, is there any relationship that says the early 2000s more than Justin Timberlake and Britney Spears's? The two met in December 1992 when both were cast in the 1990s revival of the Mickey Mouse Club, per People. In fact, he was Britney's first kiss during a Mouseketeer sleepover.

By the late '90s, both were successful in their separate music careers and were reunited in 1998 when Britney opened up for NSYNC. This sparked dating rumors that were confirmed in September 2000 when they went public at the MTV Video Music Awards. One year later the duo were living together. Justin contributed a song on Britney's third album, the self-titled Britney, but four months later in March 2002 they were calling it quits.

The end of their relationship was plagued by gossip. When Justin released "Cry Me a River" eight months after their split, fans speculated Britney cheated on him based on its lyrics and a Britney look-alike in the music video. Justin denied this and admitted to writing the song when he was in an angry place. Neither has revealed why the relationship ended though Britney did later share in her 2023 memoir that she got an abortion while dating Justin. She wanted to keep the baby, but he wasn't ready for fatherhood.