In the world of sitcoms, there are some very specific shows that have achieved a status more akin to cult followers than regular old TV viewership. One of those shows is Two and a Half Men.From the first season to the grand finale, these three guys and their bevvy of character-rich friends have given us many things to smile about. There’s nothing that surprises us more than when a sitcom goes through character arcs and plot lines that are more important than just laughing out loud one-liners.Think of Modern Family or The Big Bang Theory. Part of the joy of those shows is the fact that the characters and story lines aren’t as predictable as sitcoms of years past. But what goes on behind the scenes? While some of these sitcoms are pretty tame, it’s to be expected that anything with Charlie Sheen in it has some stories.Updated on February 6, 2023: Two and a Half Men may have wrapped in 2015, but stars Charlie Sheen and Jon Cryer have continued to keep busy. Cryer took a year off acting in 2022 after appearing in four different projects in 2021, but has an upcoming NBC comedy series he's working on that's currently in pre-production. Sheen also took some time out of Hollywood, but returned last year for the TV series Ramble On as well as producing an upcoming production called Swag.
20 Jon Cryer Hid A Specific Bag Of Stuff For Charlie
Co-stars have to look out for each other, but poor Cryer had gone above and beyond for Charlie Sheen for quite some time. Not only did he have to help Sheen on set during filming, but Hollywood Reporter also discussed the fact that Cryer had to help Sheen hide bags of naughty magazines when Sheen’s (now ex) wife came to visit his trailer!
19 Charlie Sheen’s Vegas Moment Surprised His Co-Star
We all would think that Charlie Sheen and Vegas go together like dangerous cookies and milk, right? According to Cryer, their Vegas trip turned out to be a little more tame than anyone thought it would be. Instead of hitting the town, Hollywood Reporter says that Charlie Sheen landed in Vegas and immediately hit the sack for a nap.
18 A Girl Lost Jon Cryer Because She Dated Charlie Sheen
There’s definitely something in the “code” of friends and relationships that talks about not dating your friends’ exes. While sometimes friends and exes can actually be a great fit, this situation certainly comes up.
According to Ranker, Cryer broke up with a woman he was dating because he learned she had previously dated Charlie Sheen!
17 Charlie Sheen Offered A Lot Of Money To A Woman To Stay Silent
Sheen has done a lot of questionable things, but none of them really match up to this tricky relationship situation. At one point during Sheen’s well-documented downwards spiral, he reached out to an ex who was “spreading rumors” (or maybe just telling truths) about him and his actions towards her, and told her he’d give her a lot of money to stop the slander.
16 Chuck Lorre Got Called A Clown
One of the most successful producers, Chuck Lorre’s resume includes works like Modern Family and The Big Bang Theory. Sheen, however, was not impressed, and apparently called Lorre a clown. Sheen supposedly wasn’t on board with some of the creative decisions being made.
15 Charlie Sheen Got A Raise Despite His Issues
When we act up at work, we get fired. When Charlie acts up at work, he gets a raise. Now, we’ll be honest and say that it’s more accurate to report that he got a raise in spite of his issues. And he certainly didn’t get the several millions Hollywood Reporter says that he was asking for, just one or two million.
14 Charlie Sheen And Ashton Kutcher Fought
When we say fought, we don’t mean fist to fist. Sheen decided to take him to task that old classic way of chewing him out over social media. While it wasn’t the worst argument in the history of the world, Kutcher certainly didn’t back down. He defended himself fully and firmly against Sheen’s comments.
13 Charlie Sheen’s Christmas Present Was An Arrest
The beginning of the end, or maybe somewhere near the middle of the end, Sheen had a pretty rough go at it one holiday. While this technically didn’t happen on set, it did affect his set life. Ranker says Sheen was arrested on Christmas day due to a fight with his ex-wife.
12 Relationship Advice Turned Into Financial Planning
According to The Hollywood Reporter, Charlie Sheen and Jon Cryer had a close relationship when it came to discussing relationships and giving advice. In fact, Cryer even asked Sheen for advice when it came to ladies of the night. Unfortunately for Cryer, the one he linked up with got onto the topic of financial planning instead of getting down and dirty.
11 Jon Cryer Had To Talk Charlie Sheen Down A Couple Times
This doesn’t come as a surprise. After all, it was most of what happened on the set of Two and a Half Men. When Charlie Sheen started to get a little wild, Cryer was the stable and strong person near him. We personally really liked the dynamic between them, but we’re sure that Cryer got tired of talking Charlie down from the edge.
10 Charlie Sheen’s Girlfriend's Photos Were Questionable
We’ve all heard this story before, right? It’s exactly what we’d expect from Charlie Sheen’s more volatile personality, but not necessarily from his pre-tailspin persona. According to Cryer (and Ranker), Sheen never used to show off his girlfriend’s photos. Instead, he would share pictures of other parts of them with Cryer and others.
9 Jon Cryer’s Hair Was Pretty Much All Fake
Believe it or not, Cryer’s character's hair was a little too good to be true. While it might have seemed like he was all natural, according to Daily Mail, the hair in the show is actually painted on. It’s kind of like shoe polish, but with something on top to keep it set and safe from unfortunate hand smudges.
8 Charlie Sheen Has Memorization Super Powers
This is a story that we almost couldn’t believe. Apparently, Sheen has the superpower of memorization. While all actors can memorize, Sheen’s skills are incredible. The Hollywood Reporter says, “On take two, Charlie completely nailed it. Every beat. Every line. When he absolutely had to focus, he did.” Now that’s super.
7 Charlie Sheen Refused To Leave The Couch One Day
We’ve talked a little about the beginning of Sheen’s end, and about the tailspin he got into during the end of his marriage. But what about stories on set that epitomize his crash? One story comes to us from Cryer, who said that sometimes Sheen was so far gone that he just held on to the couch instead of completing his blocking.
6 Even The Child Actor Said To Avoid The Show
Despite some of the more interesting choices that this previous child actor made, it seems like Angus T. Jones does have some common sense. First, the fact that his character was really intelligently done. And, second, the fact that he reportedly told people to avoid watching the show. This is partially due to a clash in his personal beliefs, but hey, there were a few dark seasons in there too.
5 Charlie Sheen Once Asked For $3 Million
Remember when we talked about how Sheen asked for more money, despite all of his issues? He never let it go. According to Ranker, Sheen seriously asked for his salary to be raised to $3 million. That’s more than most people make in a year... Heck, that’s more than some of us will make in our lives!
4 Charlie Sheen Also Declined The Finale
Sheen says many things, which is maybe why we were reluctant to believe him when he got grumpy about not getting to do the finale. He declined the finale, mostly because they wouldn’t do it the way he wanted them to. Yes, that’s right: Sheen, the actor, refused to come back because the production team and director had a different opinion from him.
3 Ashton Kutcher Did It For The Paycheck
Most actors will have some jobs in their lives that they do just for the money. There’s no shame in that! After all, many of us regular folks have taken contracts and careers that we’re not passionate about just to pay the bills. Ashton Kutcher is pretty open about the fact that he just took the Two and a Half Men gig for the money, which we can’t fault.
2 The Writer Was A Roseanne Reject
TV Guide gave us the inside scoop on this set secret, which is that the writer on Two and a Half Men was actually a Roseanne writer before landing on this show. While it doesn’t come as a surprise when looking at the writing, it is surprising to hear that the writer was taken off Roseanne; this is a well written show!
1 Charlie Sheen And Jon Cryer Switched Roles
Sure, actors get cast in parts that are totally unlike them all the time. But in this case, the parts ended up getting switched around to suit the actors. Sheen and Cryer were originally set to play the other one’s role, but Cryer so naturally fit the part that we’ve seen him in now. Sheen certainly fit his role, too, but seemed to grow out of it.