Both men have had a pretty active love life during their time at the top, but Sheen definitely has Kutcher beat in terms of dysfunction. Not only does he have five children with three different women, but he was also revealed to be in Heidi Fleiss’ little black book back back in the ‘90s.
Tumultuous relationships aside, all of Sheen's past hook-ups have been absolutely gorgeous. In addition to the plethora of porn stars that he has dated, Sheen was also married to actresses Denise Richards and Brooke Mueller, even though both later divorced him after citing abuse and assault. And let’s not forget about his brief engagement to Kelly Preston, which ended after Sheen shot her in the arm.
On the other hand, Kutcher had more of a traditional dating life at the beginning of his career. He would often be linked to movie co-stars such as Brittany Murphy and Amy Smart, but his bizarre marriage to Demi Moore is definitely Kutcher's romantic calling card. The former Mrs. Bruce Willis married the much younger actor in 2005, and they have since become the ideal Hollywood couple. Kutcher has even acted like a surrogate father to her kids, which is infinitely disturbing because her oldest child, Rumer, is only 10 years younger than him.
Despite the fact that Moore is 15 years older than Kutcher, he better be careful what parts of her body he's touching because, while she is old enough for him, her bust line may still be under 18-years-old.
The edge goes to: Charlie Sheen