1. Madonna Kisses Britney and Christina

At the 2003 MTV Video Music Awards, Madonna stunned the world by planting a kiss on both Britney Spears and Christina Aguilera during a live performance. The surprise moment blurred the lines between shock and art, instantly becoming a cultural landmark.
It wasn’t just a kiss; it was a powerful statement about pop icons and boundary-pushing theatrics. Fans and critics alike couldn’t stop talking about it for weeks. This bold move cemented Madonna’s reputation as the queen of reinvention and controversy.