3. BROOKE SHIELDS
When: December 1987
After Shields and Cage were photographed attending the premiere to his film Moonstruck together, the rumors of a more serious relationship between the two off the red carpet started flowing.
Smash Probability: At first, it's difficult to believe that a woman once linked to John F. Kennedy Jr. would go for Cage, but then their relationship becomes believable when you remember that she had a reputation for being one of the most controversial young starlets in the 1980s.