Just days before Spears’ memoir, The Woman in Me, hits shelves on Tuesday, October 24, resurfaced footage — seemingly from comedian Dave Chappelle’s August 24 birthday celebration — showed Timberlake, 42, singing his hit “Cry Me a River,” a song allegedly about his relationship and subsequent split from Spears, 41.
Before launching into the 2002 single, he revealed that people have warned him to ditch the track from his live performance. “They said not to do this [song] no more,” he told the crowd in the clip, which is circulating via X (formerly known as Twitter). “F—k that!”
Timberlake and Spears — who met on the set of the All New Mickey Mouse Club in the early ‘90s — made their public debut as a couple in 1999. They called it quits in 2002 after three years of dating amid reports of infidelity. “Cry Me a River” also seemed to suggest a cheating scandal, with Timberlake hiring a Spears lookalike to costar in the music video.
After its premiere in 2002, Spears told Rolling Stone that Timberlake warned her he was releasing a “controversial” video.
“He got what he wanted. I think it looks like such a desperate attempt, personally,” she told the outlet at the time. “But that was a great way to sell the record. He’s smart.”
Prior to her book’s October 24 release, a source exclusively told Us Weekly that Spears admits to making out with choreographer Wade Robson while dating Timberlake in The Woman in Me. She writes that the pair “agreed to move past” the infidelity given the years that she was “loyal to Justin” and “only had eyes for him.”
However, Spears also says that Timberlake cheated on her “a couple of times” throughout their relationship. In one instance, Spears alleges that the Grammy winner was photographed with “one of the girls from All Saints” while out in London in 2000. At a later date, she says he allegedly bragged to one of Spears’ dancers about a girl he hooked up with the night before in Las Vegas.
Over the years, Timberlake has raised eyebrows on multiple occasions for his commentary on Spears. During a 2003 appearance on 20/20, Barbara Walters asked Timberlake whether Spears had “kept her promise to wait [to have sex] until marriage.” In response, Timberlake infamously burst out laughing. In a 2006 profile with journalist Robert Haskell, Timberlake claimed that if “I was writing an article about [Britney], I would not be able to fight the urge to write every dirty thing about her.” (Screenshots of the article were shared via X by a Spears fan account on Thursday, October 19.)
Timberlake later apologized for the remarks, saying he wanted to “take accountability” for his hurtful words in a lengthy May 2021 Instagram statement. “I know I failed,” he said at the time. “I also feel compelled to respond, in part, because everyone involved deserves better and most importantly, because this is a larger conversation that I wholeheartedly want to be a part of and grow from.”
Meanwhile, as the release date for The Woman in Me looms closer, a second insider told Us earlier this month that Timberlake is trying to steer clear of the drama.
“Justin will always be supportive of Britney and all of her endeavors, but he’s trying to distance himself from her upcoming book,” the source explained. “It’s not something he’s focusing too much on in terms of anything she might discuss when it comes to their former relationship.”
Spears, meanwhile, took to Instagram on Friday, October 20, to clarify that her memoir isn’t meant to “offend anyone.” “That was me then … that is in the past!!!” she wrote.
Following his split from Spears, Timberlake went on to wed Jessica Biel in 2012. The couple share sons Silas, 8, and Phineas, 3. Spears, for her part, shares sons Sean, 18, and Jayden, 17, with ex-husband Kevin Federine. She recently separated from Sam Asghari, who filed for divorce in August after 14 months of marriage.