Hollywood superstar Charlie Sheen has been the center of tabloid rumors for decades due to his infamous party lifestyle. The Two and a Half Men actor's highly publicized personal life has been chock full of heavy drug use, volatile relationships, and bizarre interviews that have been the subject of entertainment news for years.
While there are a bevy of utterly strange incidents to choose from, a handful of Charlie Sheen moments stick out as some of the wildest moments in recent pop culture history.
Check out Charlie Sheen's wildest moments here.
What do you think was Charlie Sheen's craziest moment?
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Back in 1990, Charlie Sheen made headlines after he "accidentally" shot his girlfriend at the time Kelly Preston. The incident was a huge scandal that was never truly cleared up until 21 years later when Sheen gave his full recount of the story.
Here's Sheen's recollection of the time he "accidentally" shot his girlfriend:
"I was downstairs early in the morning making coffee and I thought she was still asleep upstairs. And I heard a f--king gunshot go off. I thought, 'She did it, she finally f--king did it. She killed herself and they're going to f--king blame me.'"
"So I abandoned the coffee, because a gunshot in the morning will wake you up better than a nice cup of coffee."
"I come around the corner and there's naked Kelly Preston at the top of the stairs, holding her wrist, staring at me, covered in blood…and I thought, that's pretty f--king hot," he said jokingly. "I didn't. I didn't."
"She explained to me when she lifted my pants off the scale in the bathroom…the tiny revolver I used to carry…it fell out of the back jeans pocket and hit the floor and shot a bullet right between her legs. So she got hit with shrapnel from the toilet bowl."
"The oddest moment…when I picked up the phone, I looked at the phone, completely perplexed, and I didn't know whether to call 911 or 411. But for years people thought, there was always this conversation, this discussion about the time I tried to kill Kelly Preston."
No charges were ever filed.
[H/T E! News]
Sheen sat down in March of 2011 with 20/20's Andrea Canning. The interview took the Internet and media by storm as the actor displayed his increasingly bizarre behavior.
The 51-year-old discussed his past and ongoing drug use, but maintained that he had everything under control. Canning pressed him on a slew of issues, and Sheen's answers seemed to become more and more odd throughout the interview.
Check out the video below:
Charlie Sheen sat down with Alex Jones of Today show, and the interview was completely strange.
This was the infamous segment when Charlie Sheen stated that he has "tiger's blood." He also explained that Alcoholics Anonymous is for people who are weak, and that he was able to cure himself of addiction.
In January of 2014, Sheen sent the tabloids into a frenzy after he claimed to marry his porn star girlfriend Brett Rossi. After only three months of dating, Sheen made an announcement on Twitter that he got hitched to Rossi during their vacation to Iceland.
He reportedly was only "kidding," and wanted to send a message to one of his ex-wives, Denise Richards. Even though the stunt wasn't a real marriage, the media still went nuts after Sheen posted the tweet.
If the marriage was real, it would have been the Anger Management star's fourth time to tie the knot at the time.
"I wanted to give Denise a stroke," Sheen said to TMZ at the time.
[H/T Daily Mail]
In 2014, Charlie Sheen allegedly attacked his dentist with a knife after having a "bad reaction" to the gas that he was given.
The dentist told TMZ that Sheen pulled a knife on him, but he was uninjured in the incident. The Los Angeles Police Department reportedly got involved to investigate the incident.
Despite what the dentist said, Sheen and his reps maintain that no such attack ever happened. Charlie's spokesperson at the time, Jeff Ballard, said: "Charlie went to the dentist and had a bad reaction to the nitrous oxide which the dentist administered to him."
While Sheen may have done some truly bizarre things in his past, the actor has shown that he is extremely generous. In 2012, he sent his Scary Movie 5 co-star Lindsay Lohan a check for $100,000 in order to help her with her $230,000 debt to the IRS.
"Charlie has a long history of helping out his friends in many ways and this is just another example of that," Sheen's spokesperson said.