15. Demi Moore's Happy, Extended Family - After a two-year courtship, Ashton Kutcher and Demi Moore tied the knot in 2005 surrounded by friends and family, including Demi's ex-husband Bruce Willis, with whom she has three children. We continue to be amazed and impressed by how well the new and old husbands get along. The three stars often vacation together!
16. Angelina Jolie's Brotherly Love - Pre-Brad and Billy Bob, Angie weirded out the world at the 2000 Academy Awards when she announced in her acceptance speech that she was "so in love" with her brother Jamie Haven, whom she later was seen kissing. On the lips. For an uncomfortably long time. In fact, their kiss lasted longer than it took for the inevitable incest rumors to start.
17. Britney, Christina and Madonna Pucker Up - Before Lindsay Lohan turned into a lipstick lesbian, before Katy Perry was kissing girls and liking it, and before Adam Lambert was simulating oral sex onstage, there was Madonna's infamous performance with Britney Spears and Christina Aguilera at the 2003 MTV VMAs. Their lingering girl-on-girl kisses had everyone else's tongues wagging too. When Lesbian Obsessions Backfire On Men
18. Britney and Justin Break Up - Friends since they were kids on The New Mickey Mouse Club, Britney Spears and Justin Timberlake ended their three-year, high-profile teen romance in 2002. Spears claimed she was devastated, but rumors of her infidelity abounded after the public saw Timberlake's video for "Cry Me a River."
19. Bennifer - When Jennifer Lopez left husband Cris Judd in 2002, she immediately began dating Ben Affleck. There wasn't a news program or tabloid that didn't analyze the glitzy relationship, and the intense media scrutiny may have caused their breakup. Just hours before their September 2003 wedding was to take place, Bennifer was no more. Both Jen and Ben went on to have successful marriages—and they'll always have Gigli.