Johnny Depp and Kate Moss
They started dating when she was 20 and he was 31. Depp was already a very successful actor and Moss was a young successful model that had everyone at her feet. They had a relationship marked by scandal, mischief, and excess that resulted in a broken hotel room worth thousands of dollars in damage. In 1997, after almost 3 years in a relationship, they decided to part ways. However, in 1998, they were seen together again during the Cannes Film Festival.