The Most Tragic Moments Of Britney Spears & Justin Timberlake’s Relationship

In November 2002, Justin Timberlake released the music video for “Cry Me A River,” featuring a Britney Spears lookalike wearing her signature hat. The song tells the story of a cheating girlfriend who clings to the man she wronged, so naturally, people put two and two together. His 2018 memoir, “Hindsight,” revealed that Timberlake wrote the song in two hours to express his complicated feelings following heartbreak. The pop star claimed he wasn’t trying to bring anyone down with his music but simply to create something that people could relate to.

In August of the following year, Spears shared her thoughts on the video with Elle. “It was hard for me that he was so exploitative,” she admitted. “Every interview that he did, he was just talking about us in such an open way and I just felt, ‘Is nothing sacred anymore?’ It was weird. It was … disappointing,” (via CBS News). When Spears spoke to Diane Sawyer for ABC’s “Primetime,” the host pressed her for answers about what really went down in their relationship. 

Initially, the “Toxic” singer dodged the question by acknowledging how devastated she felt after their romance ended, confirming it would always hold a special place in her heart. Spears also gave a rather vague response in relation to whether Timberlake’s cheating accusations were true: “I think everyone has a side of their story to make them feel a certain way,” she said. “I’m not technically saying he’s wrong, but I’m not technically saying he’s right either.”