Characters: David Aames and Sofia Serrano
Movie: Vanilla Sky (2001)

Despite a history of questionable decisions—namely, Scientology and Cocktail—Tom Cruise has managed to snag women whose average hotness hovers at approximately 9.89/10. Between his divorce from Nicole Kidman and his marriage to Katie Holmes, Cruise dated the Spanish beauty Penélope Cruz.

The two met while playing star-crossed lovers in Cameron Crowe's fantastical Vanilla Sky, and officially confirmed their relationship in 2001. The details of their break-up were resurrected recently in an article in Vanity Fair, which claimed that the three-year relationship ended because Cruz refused to convert to Scientology. The story also claimed that Scientology bosses secretly tried and failed to find a new woman for Cruise. As we said: bad decisions.