Celebrity / Charlie Sheen Charlie Sheen's 8 Worst Moments That radio rant was hardly the actor's first trainwreck moment By Evann Gastaldo, Newser Staff Posted Feb 27, 2011 4:10 PM CST Copied American actor Charlie Sheen is seen during an interview with the Associated Press at the 59th International film festival in Cannes, southern France, on Sunday, May 21, 2006. (AP Photo/Jeff Christensen) See 1 more photo Dissing the co-creator of his hit TV show may be Charlie Sheen's most costly mistake—but it's most definitely not his first. The Hollywood Reporter runs down eight previous Sheen screw-ups: 1990: While engaged to Kelly Preston, Sheen thought he heard someone in their townhouse, put his gun in his pocket, and went to investigate. Then he forgot about the gun, took off his pants, and left them in the bathroom. When Preston went to move them, the pistol went off and injured her. Is it any surprise she married John Travolta instead? 1994: Infamous madam Heidi Fleiss was indicted, and Sheen was outed as one of her clients. During his testimony at her trial, he admitted to spending more than $50,000 on her services. 1998: Tried injecting cocaine, overdosed. Enough said. 2005: While then-wife Denise Richards was pregnant with their second daughter, she filed for divorce and accused Sheen of, among other things, threatening her with violence, being attracted to underage women, and revealing his private parts on the Internet. Click for the complete list, or check out the latest on Sheen's exploits. (More Charlie Sheen stories.) See 1 more photo Report an error