Why would you pay for sex when you can go home to Elizabeth Hurley? Beats us. Grant was arrested for misdemeanor lewd conduct in June 1995 when he was caught with hooker Divine Brown in his car on Hollywood's Sunset Boulevard. He pleaded no contest, paid a fine and was ordered to complete an AIDS education program. Hurley, whom he started dating in 1987, stood by him for another five years before they split. Even better for Grant? His subsequent charming but contrite Tonight Show interview (during which Jay Leno famously asked, "What the hell were you thinking?") became a career-defining insta-classic.
Photo Credits: Jason Merritt/Getty Images; Sonja Flemming, CBS; Kevin Mazur, Getty Images for TNT; Michael Gladis; HBO; Gabe Ginsberg, WireImage; Frazer Harrison/Getty Images; Jenny Anderson/WireImage; Paul Archuleta, FilmMagic; Dan MacMedan, Getty Images