Date: 2005

Perpetual bad press magnet Charlie Sheen found himself in hot water in 2005 when a voicemail he'd left ex-wife Denise Richards in June of 2008 leaked to the press.

On the tape, Sheen is heard saying: "You’re a piece of sh*t f***ing liar and I hope you f***ing rot in hell. So f*ck you. I hope I never f***ing talk to you again you f***ing c*nt. F**k you. You’re a coward and a liar and a f***ing n***er alright, so f**k you."

Sheen later showed remorse in a formal statement: “I deeply apologize by my choice of words to all I have obviously offended; especially to Tony Todd, an African-American, who was my best man at my first two weddings."