Charlie Sheen's Former 'Goddesses'

Before he fell for Rachel Oberlin and Natalie Kenly, meet the women – Kelly Preston! Stephanie Seymour! Denise Richards! – who held the key to Sheen's heart


Dated from: 1991 – 1993
When Hollywood's madam to the stars was brought down for tax evasion in 1995, Sheen served as the star witness in her trial, admitting he had spent $53,000 on 11 of Fleiss's prostitutes. For her part, Fleiss praised Sheen to Vanity Fair, saying, "Charlie was a gentleman. [At his parties,] he'd pay for all his friends."