Exclusive: Justin Timberlake Unleashes Unfiltered Outburst in Resurfaced Footage That Shocked Everyone

Justin Timberlake once asked haters to cry him a river when it comes to singing about his breakup with Britney Spears.

Just days before the release of Spears' memoir, The Woman in Me, on Tuesday, October 24, recently surfaced footage showed Timberlake, 42, singing his popular song "Cry Me a River" at comedian Dave Chappelle's birthday celebration on August 24. The song is believed to be about Timberlake's past relationship and breakup with Spears, 41. Before performing the song, Timberlake shared with the crowd that he had been advised to no longer include it in his live performances. Defiantly, he exclaimed, "F—k that!" The clip of his performance is currently being shared on X (formerly known as Twitter).

Timberlake and Spears, who first crossed paths on the set of the All New Mickey Mouse Club in the early ‘90s, officially unveiled their relationship to the public in 1999. However, their romantic journey came to an end in 2002, following a three-year affair plagued by rumors of betrayal. Adding fuel to the fire, Timberlake's hit song "Cry Me a River" featured a doppelganger of Spears in its music video, hinting at a potential cheating scandal. In an interview with Rolling Stone after the video's release, Spears disclosed that Timberlake had forewarned her about its controversial nature.

"He successfully achieved his desires. Personally, I perceive it as a desperate endeavor," she shared with the outlet at that moment. "Nevertheless, it proved to be an effective strategy for promoting the record. He possesses cleverness."

Before the release of her book on October 24, a source revealed exclusively to We that Spears confesses to engaging in intimate acts with choreographer Wade Robson during her relationship with Timberlake in The Woman in Me. In her writing, she acknowledges that they both "decided to overcome" the unfaithfulness, considering the lengthy period of her faithfulness and unwavering devotion to Justin."

However, Spears also claims that Timberlake was unfaithful to her "a couple of times" during their relationship. In one incident, Spears alleges that the Grammy winner was photographed with "one of the girls from All Saints" while out in London in 2000. Later on, she states that he supposedly boasted to one of Spears' dancers about a girl he had hooked up with the previous night in Las Vegas.

Over the years, Timberlake has sparked controversy with his comments about Spears. In a 2003 interview with Barbara Walters on 20/20, Timberlake laughed when asked if Spears had kept her promise to wait until marriage to have sex. In a 2006 interview with journalist Robert Haskell, Timberlake admitted that if he were to write an article about Britney, he would feel tempted to include explicit details about her. (Screenshots of this article were shared on Thursday, October 19 by a Spears fan account on X.)

Timberlake later apologized for his remarks in a lengthy Instagram statement in May 2021, expressing his desire to take responsibility for his hurtful words. He acknowledged his failure and expressed his commitment to being a part of a larger conversation and learning from it.

Meanwhile, with The Woman in Me's release date approaching, a second insider revealed to Us earlier this month that Timberlake is making an effort to avoid getting involved in any drama.

"Justin will continue to show support for Britney and all her pursuits, but he is trying to keep his distance from her upcoming book," the source clarified. "He isn't giving much attention to whatever she might bring up about their past relationship."

On Friday, October 20, Spears took to Instagram to clarify that her memoir is not intended to offend anyone. She wrote, "That was who I was in the past!"

After splitting from Spears, Timberlake married Jessica Biel in 2012. The couple has two sons, Silas (8) and Phineas (3). As for Spears, she has two sons, Sean (18) and Jayden (17), with her ex-husband Kevin Federine. Recently, she separated from Sam Asghari, who filed for divorce in August after 14 months of marriage.