Crying a river! The 20th anniversary of Britney Spears and Justin Timberlake’s all-denim look brought back so many memories for the Princess of Pop’s sister, Jamie Lynn Spears.
“My parents. Divorce is hard,” the Zoey 101 alum, 29, quipped in an Instagram comment on Monday, January 11, after Nylon magazine shared a photo of the former couple in the iconic matching outfits that they wore to the 2001 American Music Awards.
While Britney and Timberlake, both 39, never married each other, they were one of the most recognizable power couples in the entertainment industry in the early aughts. The All-New Mickey Mouse Club alums started dating shortly after their music careers took off in the late 1990s, but they split in late 2002. The former ‘NSync member subsequently accused the “Toxic” singer of cheating on him.
During an emotional Primetime interview in 2003, Diane Sawyer directly asked Britney whether she had been unfaithful to Timberlake during their relationship. The Crossroads actress did not confirm or deny his allegations, telling viewers that she would let her single “Everytime,” speak for itself. (Timberlake, for his part, released a breakup track called “Cry Me a River” around the same time.)
“I think everyone has a side of their story, to make them feel a certain way,” Britney told Sawyer. “I’m not technically saying he’s wrong, but I’m not technically saying he’s right either.”
The “Womanizer” songstress went on to elope with her childhood friend Jason Alexander in Las Vegas in January 2004. Their marriage was annulled 55 hours later. That October, she wed backup dancer Kevin Federline, with whom she welcomed sons Preston and Jayden in September 2005 and September 2006, respectively. Britney filed for divorce from Federline, now 42, in November 2006, and they finalized the case in July 2007. The Britney and Kevin: Chaotic costars now coparent their 15- and 14-year-old sons.
“They’re cordial but don’t do very much as a family,” a source exclusively told Us Weekly in December 2019, noting that “Preston and Jayden are either with their mom or dad, very rarely both parents.”
The Louisiana native has been in a relationship with personal trainer Sam Asghari since late 2016.
Timberlake, for his part, dated Jenna Dewan and Cameron Diaz after Britney. He began seeing Jessica Biel in January 2007, and they tied the knot in October 2012. The “Mirrors” singer and the 7th Heaven alum, 38, welcomed son Silas in April 2015 and a second child in 2020 whose name and sex they have yet to reveal.
“The baby is cute, of course,” Timberlake’s former bandmate Lance Bass teased to Entertainment Tonight in September 2020. “It’s Justin and Jessica!”
Listen to Us Weekly’s Hot Hollywood as each week the editors of Us break down the hottest entertainment news stories!