Ashton Kutcher & Demi Moore
Demi Moore makes her second appearance on this list, unfortunately for her. After spending 13 years married to a man whose professional image revolves around his lack of hair, she went for a man who is known in part for his abundance of hair.
Ashton and Demi made news for their relationship, which included a 15-year age difference. As fun as the marriage looked form the outside, things fell apart and by 2013 their divorce was finalized.