Play Justin Timberlake’s “Cry Me a River” through Alexa. Play Britney Spears’ song “Every time” after that.
Fans are still interested in Timberlake and Spears’ tumultuous relationship even though they broke up twenty years ago, especially following the February 2021 airing of The New York Times PresentsFraming Britney Spears.
The pop princess and ex-boyband member connected while filming The Mickey Mouse Club in the early 1990s. As their careers took off in 1999, Timberlake and Spears revealed their relationship.
I still feel the same way about him as I did two years ago. But compared to when I was younger, my love is stronger now. Spears raved in 2001 to The Observer. Like, we’ve been friends since we were 12 years old, and we’ve been through a lot together. Every inch of each other is known.
The singer of Oops! I Did It Again confirmed Timberlake was the one who pursued her in that same year.
Without a doubt, he asked me out. He knocks on the door and asks, “Can I see Britney?” This was before Baby One More Time came out, and we were recording a radio show. She thought back to Rich & Famous. And Felicia [Culotta], my assistant, said that she was unaware of his identity. So who are you? And I said, “No!” Hello, Justin!
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The pair’s relationship ended in early 2002, despite the fact that they frequently gushed over one another and made headlines for wearing matching denim ensembles at the 2001 American Music Awards. After Timberlake published his song Cry Me a River and disclosed their relationship to Barbara Walters, their breakup soon descended into chaos.
Yes, Timberlake jokingly said in the 20/20 interview when asked if Spears, who had previously stated that she intended to wait until marriage to have sex, still had morals.
When asked if he f ked Spears in a radio interview that same year, Timberlake responded, “OK, I did it.”
Spears appeared to respond to the accusations that she had cheated on Timberlake in her 2003 ballad, every time, when she sang, “I may have made it rain/Please forgive me/My weakness caused you pain/And this song is my apology.”
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Framing for 2021 Britney Spears showed archival clips of Timberlake and Britney’s post-split interviews and media coverage and focused on the pop star’s conservatorship battle with her father Jamie Spears and the #FreeBritney movement. Following that, fans rushed the SexyBack singer’s social media accounts, pleading with him to retract using her to start his solo career.
For a timeline of the highs and lows of Spears and Timberlake, scroll down: