6. Britney Spears and Justin Timberlake
When Mouseketeers-turned-teen-superstars Brit and JT fell in love, it almost seemed like everything was right in the world for a little while. Between Justin’s frosted tips and Britney’s girl-next-door smile, it was a match made in denim-clad 90s heaven. In fact, we’re fairly certain that if the sad split had never happened, the world would not have had to witness the head-shaving Britney meltdown.