#14: Angelina Jolie and Her Brother Share a Kiss
When: 72nd Academy Awards, Vanity Fair Oscar Party 2000
Perhaps the most infamous kiss that set tongues wagging for all the wrong reasons was Angelina Jolie locking lips with her brother, James Haven, at the 2000 Vanity Fair Oscar party. Clad in matching goth attire, their overly long embrace raised more than a few eyebrows.

Jolie’s speech upon winning Best Supporting Actress for Girl, Interrupted only fueled speculation. “I’m in shock. And I’m just so in love with my brother right now,” she declared, her words ringing with an unexpected fervor. Twenty-four years have since passed, and we are all still completely shocked by this event…