26 year old anna nicole smith at her wedding with 89 year old billionaire howard marshall (1994)
Their marriage lasted 14 months before James died of an infectious disease at the age of 90. Throughout this time, Anna took care of him and stayed by his side until the end. Many believed she was waiting for his death to inherit his wealth. However, the old man left her nothing. Infuriated, Anna filed a lawsuit against her stepson to claim some compensation. Despite several years of legal battles, Anna was unable to secure any inheritance.