More than two decades ago, the pop star and Justin Timberlake were once one of the most famous A-list couples on the planet. Britney and the former ‘NSync performer met while filming The Mickey Mouse Club in the ’90s and went public with their romance in 1999, going on to wear their matching denim ensembles at the 2001 American Music Awards.
Their breakup made headlines in 2002, the same year he released his hit single “Cry Me a River,” inspired by the rocky end of their red-hot romance and her speculated infidelity.
Following their split, Britney was romantically linked to a few men, including choreographer Wade Robson as well as actor Colin Farrell, before she surprised fans by marrying her childhood friend Jason Alexander in January 2004 at the Little White Wedding Chapel in Las Vegas, Nevada.
Their union was short-lived, as the couple annulled their union after just 55 hours of being married. Britney filed a petition with the court, which stated that she “lacked understanding of her actions” at the time.
Ahead of her 2022 nuptials to Sam, Jason allegedly trespassed into her house and livestreamed the incident on social media. The Ventura County Sherrif’s Office confirmed to In Touch that they “[responded] to a call at the residence for a trespass” and Jason “was contacted and arrested” for “an out of county warrant.”
Britney also ended up marrying her next husband, Kevin Federline, in 2004. Following their nuptials in September of that year, Britney and Kevin’s wedding was legalized a few weeks later in October, and the couple welcomed two children while they were together: Sean Preston in 2005 and Jayden James in 2006.
As their relationship fell apart, she struggled with mental health, which resulted in the beginning of her conservatorship in 2008. The now-exes split in 2006, and their divorce was finalized by July 2007.
Although she was romantically linked to other suitors in the wake of their divorce, it was Sam who ultimately won her heart and helped support the “Gimme More” singer through her conservatorship battle in 2021.
Fans were overjoyed when a California judge officially terminated Britney’s conservatorship after 13 years following the #FreeBritney movement and documentaries inspired by her life story.
The ruling November 12, 2021, allowed her to finally make her own medical, financial and personal decisions for the first time since 2008.
“History was made today. Britney is Free!” Sam wrote while celebrating her legal victory, just two months after he popped the question in September 2021.
Scroll through the gallery below to look back at Britney’s dating history.
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