In the '90s, Demi and Bruce were one of Hollywood's hottest power couples. Even so, on June 24, 1998, they called it quits after 11 years of marriage. They didn't file for divorce until Oct. 18, 2000 -- reportedly because it took that long to sort through their $20 million worth of real estate in Hailey, Idaho, and to make sure their daughters were OK -- but once they did, it was finalized the next day.
But that wasn't the only bad news Demi encountered in 1998. In July, her mother, Virginia, died from a brain tumor. Demi and her mother hadn't been on speaking terms for most of the '90s after Virginia walked out on a substance-abuse rehab program that Demi had paid for. Luckily, they reconciled shortly before Virginia's death.