Britney Spears and Justin Timberlake were known as pop culture royalty when they dated in the early 2000s, but their breakup divided fans for nearly 20 years.
Britney Spears and Justin Timberlake were pure pop royalty in the late ’90s and early 2000s, so it’s no wonder the world was obsessed with their relationship. The “Baby One More Time” singer and NSYNC frontman seemed like they were perfect for each other when they went public in 1999. It was all cute soundbites and PDA-packed red carpet appearances until things came crashing down in 2002, amid rumors of cheating and lies.
Following the split, Justin appeared to shade Britney in his “Cry Me a River” music video and made eyebrow-raising comments about their relationship in interviews, fueling public scrutiny toward Britney just as she was grappling with mental health struggles.
Over the years, both moved on — Justin married actress Jessica Biel in 2012, while Britney wed dancer Kevin Federline in 2004 (they divorced in 2007) and later married actor Sam Asghari in 2022 before their 2023 separation. Still, their shared history has remained a major talking point, especially after Britney’s 2023 memoir The Woman in Me revealed new details about their relationship, including claims that Justin cheated and that she had an abortion during their time together. It took nearly two decades for the “SexyBack” singer to finally apologize to his ex, seemingly prompted by a surge of support for the star amid her 2020s-era conservatorship battle.
So is everything good between Britney and Justin now? Take a look back at the exes’ romance and where their relationship stands now in our timeline, right here.
Britney and Justin were both cast in The All-New Mickey Mouse Club back in 1992. At the time, Britney and Justin were both around 11 years old. The show also featured future stars Christina Aguilera and Ryan Gosling and ran from 1993 to 1996.
Following the series, Britney returned to Mississippi. She eventually came back to New York City to pursue her singing career, however. Justin, meanwhile, was recruited as a member of the boy band NSYNC.
Though they parted ways, the songstress seemed to have left an impression on Justin. He told GQ in 2006, “I was in love with her from the start. I was infatuated with her from the moment I saw her.”
Fame eventually reunited Britney and Justin eventually, who began dating in 1999 as both of their careers began taking off. Talking about their connection with The Observer in 2001, Britney, “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.”
As their relationship progressed, Justin and Britney became red carpet regulars. One of the couple’s most iconic moments came at the American Music Awards in January 2001, just weeks before their joint Super Bowl performance. While walking the red carpet, Justin and Britney wore matching, head-to-toe denim outfits.
In the years since the pair walked the red carpet together, both have commented on the fashion choice. In a 2021 interview with The Hollywood Reporter, Justin admitted he had some fashion “regrets” from his early years. “I confess that there was maybe a period in the ’90s where I could skip over some of the outfits that were public,” he shared.
Britney, on the other hand, looked back on the moment fondly. “I guess my denim was a hit years ago,” Britney commented on a photo of two toddlers recreating the outfit back in Aug. 2020.
With both stars at the top of their game, it was only a matter of time before they shared a massive stage. Fans of Britney and Justin were treated to a joint performance by the pair at the Super Bowl XXXV halftime show on Jan.
