15) Britney Spears and Justin Timberlake

Britney Spears and Justin Timberlake ended their relationship in 2002 after three years of dating. The breakup became infamous due to Timberlake’s hit song Cry Me a River, which many believed hinted at Spears’ alleged infidelity. Spears later revealed that the split was a devastating experience for her, amplified by Timberlake’s public comments and the media frenzy that followed. The breakup left a lasting impression on Spears, marking a painful moment in her highly scrutinized career.
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Edited by Apoorva Jujjavarapu