Billy Corgan and Jessica Simpson. (Photo: Archive)
Cameron Diaz and Benji Madden. (Photo: Archive)
Tom Cruise and Cher. (Photo: Archive)
Simon Cowell and Carmen Electra. (Photo: Archive)
Rihanna and Shia LaBeouf. (Photo: Archive)
Evan Rachel Wood and Marilyn Manson. (Photo: Archive)
Britney Spears and Colin Farrell. (Photo: Archive)
Michael Jackson and Lisa Marie Presley. (Photo: Archive)
Richie Sambora and Cher (again). (Photo: Archive)
Mariah Carey and Nick Cannon. (Photo: Archive)
Natalie Portman and Moby. (Photo: Archive)
Richie Sambora (again) and Heather Locklear. (Photo: Archive)
Michael Jackson (again) and Brooke Shields. (Photo: Archive)
Marc Anthony and Chloe Green. (Photo: Archive)
Madonna and Dennis Rodman. (Photo: Archive)
Lena Dunham and Jack Antonoff. (Photo: Archive)
Sean Lennon and Leelee Sobieski. (Photo: Archive)
Laura Dern and Ben Harper. (Photo: Archive)
Lady Gaga and Taylor Kinney. (Photo: Archive)
Chad Kroeger and Avril Lavigne. (Photo: Archive)
Justin Timberlake and Fergie. (Photo: Archive)
Josh Groban and January Jones. (Photo: Archive)
Shia Labeouf and Hilary Duff. (Photo: Archive)
Heidi Klum and Seal. (Photo: Archive)
Courtney Love and Edward Norton. (Photo: Archive)
Colin Farrell and Elizabeth Taylor. (Photo: Archive)
Billy Corgan (again) and Tila Tequila. (Photo: Archive)
Avril Lavigne and Brody Jenner. (Photo: Archive)
Ashley Judd and Michael Bolton. (Photo: Archive)
Andre Agassi and Barbra Streisand. (Photo: Archive)
Ryan Reynolds and Alanis Morissette. (Photo: Archive)
Adam Duritz and Jennifer Aniston. (Photo: Archive)
Katy Perry (again) and Josh Groban (again). (Photo: Archive)
Adam Duritz and Courteney Cox. (Photo: Archive)
When the stars in this list started dating, we all raised an eyebrow in unison. Some because one was way older than the other, others because they just looked weird together. Some were downright mind-blowing, because Billy Corgan dating Jessica Simpson is just…
