At the very beginning of his career, Tom Cruise had the chance to get to know the pop icon Cher for the first time. Even though Cher is about 16 years older (he was 23 then and she was 39), the two still got into a relationship with one another. Cher even opened up about their romance during an interview once explaining how she considered Cruise to be one of her top 5 Lovers. Unfortunately, their relationship only lasted a few months.