Cost: Undisclosed
Date: 1991 

MC Hammer filed for bankruptcy in 1996 but five years prior, he was living it up with a 40 person entourage and a full stable of horses. One of his thoroughbreds even ran in the Kentucky Derby. With 19 thoroughbred horses, Hammer reportedly shelled out $450,000 to buy one horse and $1.2 million to purchase another, all within the same week. Smart business moves.