Shooting Heroin at Charlie Sheen's House

Year: 1990s

What happened? After watching both of these high-profile celebrities unravel in the public eye, it makes sense that their insanity crossed paths at some point. Love revealed that back in the '90s, her love affair with heroin began one night at Charlie Sheen's mansion.

"A Hollywood-connected beau took me to this star-studded party at Charlie Sheen's house in Malibu," she recalled. "Tom Cruise was there, and Madonna ... [singer Jennifer Linch] convinced me to shoot up. 'Come on, everyone's doing it.' So that's when my whole heroin drama began."