Justin Timberlake and Britney Spears were arguably the most popular couple of the late ’90s and early 2000s. Between their childhood sweethearts love story, matching denim outfits, and genuinely sweet moments together, there really was nothing not to obsess over. While many fans expected to see them together for years to come, their romance ended abruptly in 2002. It didn’t take long for cheating rumors to surface, and Justin definitely didn’t deny or try to hide the fact that Britney broke his heart. In addition to implying in a Saturday Night Live skit that he took her virginity, he also gave a sarcastic answer in an interview when Barbara Walters asked him if Britney had been unfaithful (he replied "sure" with a smile while looking directly at the camera).
Justin poured his heartache into his music, and released the scathing breakup track "Cry Me a River" shortly after their split. While he’s never confirmed if the song is definitely about his ex, the lyrics are pretty clear ("You don’t have to say what you did / I already know, I found out from him") and the Britney look-alike in the music video speaks volumes.
The next year, Britney appeared to respond with her own song "Everytime," which also seems to confirm that she cheated on him. With lyrics like "I may have made it rain / Please forgive me / My weakness caused you pain / And this song’s my sorry," and the music video of her attempting suicide, she was very honest about just how devastated she was by the whole thing. And while they’ve both moved on (he’s been married to Jessica Biel since 2012, she’s currently dating Sam Asghari), there romance is still one that people always love to look back on (and be heartbroken over).