Previously dubbed as one of the “world’s biggest breakups” by Britney Spears herself, her relationship with Justin Timberlake recently bubbled to the surface following the former’s bombshell revelations about her ex in her upcoming memoir, Woman In Me.
The former couple didn’t begin dating over five years after they first met on the set of the revival of The Mickey Mouse Club in 1992.
Spears and Timberlake were only 11 years old when they were cast alongside Ryan Gosling, Christina Aguilera, and JC Chasez on the show.
The duo later reunited in late 1998 after the Toxic singer opened for Timberlake’s band *NSYNC in Concert tour.
The rumors of their budding romance began swirling only months into 1999, however, the pair refused to comment on the status of their relationship at the time.
After being linked together at the age of 17, Spears and Timberlake went public with their romance a year later at the 2000 MTV Video Music Awards. Both of them were 18 at the time.
Britney Spears and Justin Timberlake set the stage on fire with their electrifying performance at the annual Super Bowl Halftime Show. Aerosmith, Nelly and Mary J. Blige were among the guest artists to join *NSYNC onstage alongside Spears.
The couple moved in together in September.
Tensions ran high among the couple when Spears said that she was "not in an intense relationship with anyone at the moment," while promoting her film Crossroads in London.
She later clarified that the pair hadn’t broken up, however, noted they "did not get to spend much time together because of work commitments."
Timberlake confirmed their split in June, revealed he’s "heartbroken" over the split.
The *NSYNC star released a "revenge song" against the Womanizer singer, featuring her look-alike in the music video.
The song alluded to Spears cheating on him during their relationship.
She later dubbed his move "exploitative," though she did remain coy about the cheating rumors.
The Crossroads star posted an Instagram video of herself dancing on a balcony to Timberlake’s song Filthy. She took to caption to compliment her ex on his music, alongside a reference to their split.
"I know we had one of the world's biggest breakups 20 years ago…. but hey the man is a genius!!!!" Spears wrote. "Great song JT!!!!!"
Timberlake sent out a public apology to Spears for his behavior surrounding the couple’s breakup years ago.
He also apologized to Janet Jackson after he exposed Jackson’s breast during their 2004 Super Bowl halftime performance.
"… I specifically want to apologize to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed," he wrote on his Instagram.
In an excerpt from her memoir, Spears revealed that she had an abortion after the singer got her pregnant during their three-year relationship.
"… Justin definitely wasn’t happy about the pregnancy. He said we weren’t ready to have a baby in our lives, that we were way too young," she wrote.