Tiger Woods

When: 2006-2007
According to Madam Michelle Braun, she had sent numerous escorts for dates with Tiger Woods, hiking his bill up to a total of $60k. Braun told the press that she would sometimes send him two girls at a time because he "liked girl-on-girl" action. Given Woods' total of 19 mistresses who've come forward, including Jamie Junger (a woman who worked for Braun but did not meet Tiger through her), this allegation isn't difficult to believe.