The 9 Most Outrageous Things Charlie Sheen Has Done Since His Infamous Meltdown

  • Oops!
    Something went wrong.
    Please try again later.
  • Oops!
    Something went wrong.
    Please try again later.
·Editor, Yahoo Entertainment
In this article:
  • Oops!
    Something went wrong.
    Please try again later.
  • Oops!
    Something went wrong.
    Please try again later.
(Illustration by Paul A. Rosales, Photo by Munawar Hosain/Getty Images)
(Illustration by Paul A. Rosales, Photo by Munawar Hosain/Getty Images)

The word "outrageous" is thrown around a lot, but it's never more appropriate than when describing actor Charlie Sheen. He often evokes the first definition that the Merriam-Webster Dictionary provides for the word: "exceeding the limits of what is usual."

He was the best example of the word (at least publicly) in his 2011 meltdown, when he was "winning" and calling everyone "trolls" in a bizarre series of events that ended with him being fired from the hit CBS show Two and a Half Men.

Of course, he bounced back from that and by 2012 had come to laugh about it. "I'm not crazy any more," he said during a press conference to promote his new project for FX, the appropriately titled Anger Management. "That was an episode."

But Sheen's behavior continues to be far from the norm. As the star turns 50 on Sept. 3, we look back at a few of the post-meltdown things he's done that raised eyebrows.

1. Volunteering to serve as vice president under President Donald Trump. Actor Owen Wilson compared volatile Republican presidential candidate Donald Trump to Sheen in an August interview, sending Sheen straight to Twitter. While the Major League star had bashed Trump before, calling him "a shame pile of idiocy" and more, he had obviously changed his mind. "If Trump will hv me I'd be his VP in a heartbeat! #TrumpSheen16," he wrote. You're hired? 

(CBS)
(CBS)

2. Greeting a fan at a Taco Bell drive-thru while "hammered." We get it, sometimes you just need to make a late-night run to the border. But what was more unorthodox about Sheen's fast-food meal was that he got out of his car to talk to a fan. While Sheen admitted in the recorded encounter with his fellow taco lover that he wasn't in the best mental condition, he took the time to politely show off his chest tattoo of Charlie Brown. 

3. Adopting a flamingo with his former porn star girlfriend... wait, fiancée. Where to begin with this one? Sheen and Brett Rossi, who's more than 20 years younger, stepped out in public together for the first time in November 2013. By February 2014, they had announced their plans to marry. The two were so in sync that he revealed in March 2014 that the couple had sponsored a flamingo at the zoo in Santa Barbara, California, named Klay-vinn, a phrase he often uses in his tweets.

Sheen and Rossi embrace their adopted pet. (Twitter)
Sheen and Rossi embrace their adopted pet. (Twitter)

Related: Charlie Sheen's Ex-Fiancée Brett Rossi Goes on Twitter Tirade About Him, Hookers, and Drugs

Rossi — who began using the name Scottine Sheen — would have been the fourth Mrs. Charlie Sheen, but the wedding never happened. "Scotty and I had a great year together as we traveled the world and crossed a lot of things off our bucket list," he explained in a statement issued a month before the wedding was scheduled to take place. "She's a terrific gal — but we've mutually decided to go our separate ways and not spend the rest of our lives together. I've decided that my children deserve my focus more than a relationship does right now. I still have a tremendous fondness for Scotty and I wish her all the best." 

About those kids... 

4. Asking his Twitter followers to attack children. After his then 9-year-old daughter Sam (with ex-wife Denise Richard) was bullied at school, Sheen issued what he termed a "legitimate call to arms" via Twitter. "My daughter Sam was bullied out of Viewpoint school and then called a liar," he ranted to his 9.1 million followers. "It's on! if you have a rotted egg a roll of toilet paper or some dog sh**; I urge u to deliver it with "extreme prejudice" to their KamPuss run by trolls and charlatans. make me proud." The school responded with a statement noting that officials were "concerned." Um, can you blame them? 

Sheen huddles with Denise Richards and daughters Lola, left, and Sam. (Instagram)
Sheen huddles with Denise Richards and daughters Lola, left, and Sam. (Instagram)

5. Flipping out at Denise Richards. Sheen and Richards, who was his wife from 2002 to 2006, have had a rocky relationship for years. One day they're on vacation together, the next he's calling her a "washed up piglet shame pile" on social media, like he did this year on Father's Day. Sheen also referred to his daughter's mom as the "worst mother alive" and a lot more not worth repeating in an "open letter to the media" on his website. Good times! Despite the public jab, Sheen must feel somewhat grateful for the mother of Sam, now 11, and 10-year-old Lola. Although Richards had a restraining order against him after they first split, she's now bringing up his girls and, at times, has even taken in his twin sons with another ex-wife, Brooke Mueller, while Mueller was dealing with substance abuse.

Related: Denise Richards and Charlie Sheen Come Together for Daughter's Birthday

6. Looking for the Loch Ness Monster. In July 2013, TMZ reported that Sheen took two friends on a private jet to Scotland, where they took only a bottle of scotch out on a rented boat in search of the creature. Lavinia Turner, general manager of the Aldourie Castle Estate where Sheen and co. stayed, confirmed the adventure. "All I can say is that Mr. Sheen and his party were perfect guests and thoroughly enjoyed their trip to Scotland and Loch Ness," she told the U.K.'s The Mirror. "They had a wonderful and relaxing time but unfortunately didn't see any sign of Nessie, although I'm sure they'll be back in the future to try again."

7. Giving Lindsay Lohan $100,000. Not many people would give Lindsay Lohan the benefit of the doubt in 2013. She was still in legal trouble and had worked little since Machete. But Sheen, who worked with Lohan on Scary Movie 5 and when she was a guest star on Anger Management, did. The actor explained that he sent the actress a check to cover taxes she owed, because he was offered $250,000 to her $100,000 to do the horror spoof. "Paying it forward," he noted to The Daily Beast

Sheen worked with Lohan twice in 2013. (WireImage)
Sheen worked with Lohan twice in 2013. (WireImage)

8. Turning a visit to the dentist into a lawsuit. Dental work is typically an unpleasant experience, but how often does it go so badly that a person gets sued? Sheen managed to rack up a lawsuit charging him with assault and battery after sitting in the chair during a September 2014 appointment. Dental technician Margarita Palestino filed for unspecified damages after she said Sheen grabbed her bra, punched her in the chest, lunged at her, and threatened her life. Sheen's rep said his client had a bad reaction to the nitrous oxide used at the office along with the pain medication he was taking for an injured shoulder. While the rep admitted Sheen had knocked over dental instruments, he said much of the suit was false.

9. Ranting over Twitter at Rihanna, Kim Kardashian, and many more. When Sheen and his former fiancée Rossi noticed RiRi eating at the same L.A. restaurant as them in May 2014, the actor was hoping for an impromptu meet and greet since Rossi's a huge fan and, well, he is Charlie Sheen. Unfortunately, Rihanna declined. The nerve!  One of Sheen's Twitter tirades ensued.

(Two and a Half Men/CBS)
(Two and a Half Men/CBS)

Then, eight months later, Kim Kardashian became his target, quite possibly because of her backside. "You are lucky that ANYONE cares about your gross and giggly [sic] bag of funk you dare call an ass," he wrote in the tirade. Sheen later apologized, but Kardashian didn't publicly accept.

Here's to a year of Sheen saving his most dramatic moments for the screen.