Tom Cruise and Katie Holmes (16 years)
Tom Cruise has been a megastar for decades with a list of hit movies too long to name here. Tom has also been a notorious ladies’ man, dating some of the most beautiful women in the world. But Tom is a bit different that others here as he likes to be with other accomplished actors such as Kim Bassinger, Mimi Rogers, and Katie Holmes, who was 16 years his junior. While Katie and Tom are no longer a couple, they do share children together and have a very amicable relationship.