#21: Dorothy Hamill
Millions of girls copied her short wedge haircut after Dorothy Hamill won Olympic gold in figure skating in 1976. She became an instant celebrity with endorsement deals and even her own doll. Years later, she and her husband decided to buy a famous ice skating show.

In 1993, they purchased the struggling Ice Capades, hoping to save it. Instead, the show kept losing money, and Hamill filed for bankruptcy in 1996. Her marriage ended too. She kept skating, coaching, and performing, survived breast cancer, and later competed on Dancing with the Stars.
