4. Charlie Sheen

At one point is his life, it seemed Charlie Sheen had it all, or most of it at least- a successful Hollywood career, loads of money, his health and his fairly good looks.

Unfortunately, all that has changed over the past 5 years or so, when Sheen’s downward spiral brought down all the good things he had going for him.

As far as the ladies go, he has been married three times, to model Donna Peele, actress Denise Richards, and actress and socialite Brooke Mueller.

He has been linked to the madam Heidi Fleiss scandal, claiming he spent $50,000 on prostitutes.

Most of his girlfriends were adult film actresses, nude models and actresses, but the reason why Sheen is on our list is because his destructive habits of drinking and doing drugs, coupled with his age, have made him very ugly.