Justin Timberlake Sings “Cry Me a River” Amid Britney Spears Memoir Release

Justin Timberlake is back in the spotlight as Britney Spears’ memoir, “The Woman in Me,” prepares to hit bookshelves, reviving memories of their tumultuous past. In a resurfaced video from comedian Dave Chappelle’s birthday celebration, Timberlake is seen performing his hit song, “Cry Me a River,” which has long been associated with his breakup with Spears.

Addressing the audience, Timberlake admitted that he was advised against performing the song, given its controversial history. However, he defiantly exclaimed, “F—k that!”

Timberlake and Spears, who began dating after meeting on the set of “The All New Mickey Mouse Club” in the early ’90s, became a high-profile couple in 1999. Their relationship came to an end in 2002 amid allegations of infidelity, which “Cry Me a River” alluded to by featuring a Spears lookalike in its music video.

Spears, who previously described the video as a “desperate attempt,” also revealed that Timberlake warned her about its controversial nature before its release.

Spears’ memoir, scheduled for release on October 24, reportedly delves into the infidelity during her relationship with Timberlake. She acknowledges making out with choreographer Wade Robson while still dating Timberlake, but they agreed to move past it. Spears also alleges that Timberlake cheated on her multiple times, including an incident involving a member of the girl group All Saints and another in Las Vegas.

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Over the years, Timberlake has faced criticism for his comments about Spears. In a 2003 interview with Barbara Walters, he laughed off a question about whether Spears had kept her promise to wait until marriage for sex. In a 2006 interview, he made inappropriate comments about Spears that he later apologized for in a May 2021 Instagram statement.

As the release date for “The Woman in Me” approaches, insiders suggest that Timberlake is attempting to distance himself from the impending drama. While he remains supportive of Spears, he is not focusing too much on the content of her memoir, emphasizing his desire to grow and learn from past mistakes.