In the past, Justin Timberlake defiantly brushed off his critics, challenging them to “cry him a river” when it came to his emotional performances about his breakup with Britney Spears. Recently, just days before the release of Spears’ memoir, “The Woman in Me,” which is set to hit bookshelves on October 24, an intriguing video surfaced.
The footage appeared to be from comedian Dave Chappelle’s birthday celebration on August 24 and showed Timberlake, now 42 years old, belting out his 2002 hit “Cry Me a River,” a song widely believed to be inspired by his tumultuous relationship and eventual split with Spears, who is now 41.
Before launching into the song, Timberlake shared with the crowd that some people had advised him against performing it live. He declared, “They said not to do this [song] no more.” In a clip making the rounds on social media, he emphatically responded, “F—k that!”
To provide some context, Timberlake and Spears initially met during their shared time on the set of the All New Mickey Mouse Club in the early ’90s. They went public as a couple in 1999 but eventually called it quits in 2002 amid allegations of infidelity. “Cry Me a River” appeared to allude to a cheating scandal, as Timberlake even went so far as to cast a Spears lookalike in the song’s music video.
Shortly after the song’s release in 2002, Spears spoke to Rolling Stone about how Timberlake had warned her that the video would be “controversial.” She had her own thoughts on the matter, saying, “He got what he wanted. I think it looks like such a desperate attempt, personally, but that was a great way to sell the record. He’s smart.”
Before the release of her book on October 24, a source disclosed that Spears would admit to kissing choreographer Wade Robson while she was dating Timberlake. According to her, they both agreed to move past this infidelity, as she had been loyal to Timberlake for many years. Spears also alleges that Timberlake cheated on her “a couple of times” during their relationship. She claimed that he was photographed with “one of the girls from All Saints” while they were in London in 2000. On another occasion, she states that he bragged to one of her dancers about an encounter with a girl the night before in Las Vegas.
Over the years, Timberlake made controversial remarks about Spears, including a 2003 appearance on 20/20 when Barbara Walters questioned him about whether Spears had kept her promise to abstain from sex until marriage, to which he infamously burst into laughter. In a 2006 interview, he hinted at writing explicit things about Spears if he were to write an article about her, which subsequently caused backlash. He later issued an apology for these comments in May 2021, expressing a desire to take responsibility for his hurtful words.
In the lead-up to the release of “The Woman in Me,” another insider revealed that Timberlake is attempting to distance himself from the upcoming drama, although he will continue to support Britney in her endeavors.
Spears herself addressed the memoir on Instagram, clarifying that her intention is not to offend anyone. She emphasized that her book reflects her past self and the past events.