Years Active: 1972-Present

Ric has had a ridiculous amount of problems. From defaulting on home loans to owing the government nearly $1 million in back taxes. He got in trouble for allegedly sexually harassing flight attendants by twirling his dick around while wearing nothing but a cape. He's had abuse allegations from three of four wives, had to pay outrageous alimony's, and had to deal with wife No. 3 breaking into his house. Last September, it was announced that Ric would be going through his fourth divorce (he should've known things would be bad when she punched him three months after their honeymoon.) He's (allegedly) gotten into a fist fight with his son at a wedding and his daughter's boyfriend at a later date. When the cops came his daughter kicked one of them.

He advertised a company called Ric Flair Financial (at both NASCAR and WWE events) that turned out to be "completely illegal" and was immediately terminated. He gave each of his kids a $1,600 a month allowance while buying his cop-kicking little girl a Porsche (this is after all his financial defaults).