Two And A Half Men: 20 Things That Don't Make Sense About Charlie Harper

For 12 seasons, Two and a Half Men was one of the most popular shows on television. It launched the career of Jon Cryer and re-launched the careers of both Charlie Sheen and Ashton Kutcher. Until 2003, Sheen was mostly known for his movie work in the Major League and Hot Shots! movies, although some TV fans knew him from his stint on Spin City. His character on Two and a Half Men was modeled after his own life as a famous actor.

Succeeding Everybody Loves Raymond was not an easy task, but Two and a Half Men quickly found an audience with its cutesy premise and edgy humor. As the show took off, Sheen became the focal point, but not always in a good way. After season seven, he announced that he was taking a break from the show in order to go to rehab; what followed was a seemingly endless on-again, off again, relationship with the show, culminating with the producers deciding to write him out of the show for good and replace him with the less funny Kutcher.

Despite his on-screen (and off-screen) antics, Charlie’s attitude struck a chord with viewers. His character arc didn’t always make sense though, and throughout the series, we came to realize there were things about him that just didn’t track. In this list, we’ll look at some of Charlie’s traits that don’t seem to make sense. Have a look at our picks and let us know in the comments what you noticed about Charlie that isn’t consistent with the rest of the show.

Here are 20 Things That Don't Make Sense About Charlie Harper.

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There are a bunch of things about Charlie’s birth story that just don’t track. First, his mother Evelyn apparently gave birth to him at 7 ½ months - which in itself isn’t unusual as babies are born prematurely all the time – but if that was the case, it wasn’t fully explained in the show. Then, Charlie was supposed to be a girl as his ultrasound didn’t show any, ahem, male parts.

Furthermore, Charlie was supposedly a drama queen growing up, but that part doesn’t seem to match his personality. Yes, he’s high maintenance and relies on a lot of other people to do things for him, but he’s not a diva and generally doesn’t boss people around or get upset when things aren’t done exactly the right way.


As the first born child, he asked his parents for a sibling. They agreed, and thus his brother Alan was born. Things start to veer when you look at how Charlie has treated Alan for most of his life though. He bullied Alan growing up, making fun of him on his first day of school and giving him wedgies whenever he could.

Charlie even told his friends that Alan was his shaved monkey growing up, since he always wanted one, causing Alan to be ridiculed at school. The abuse continued into adulthood to the point where Charlie criticizes Alan and Jake for always being around. This hardly seems like the actions of a guy who really wanted a brother as a kid.


Where do we start with this one? Not only did Charlie lip something into Alan’s pocket as a kid to make him look like he was shoplifting, but he also used Alan as a pawn all the time. Charlie started drinking and chain smoking as a teenager, and ran away several times. This caused him and Alan’s relationship with their mother to be strained, but luckily for Charlie, she didn’t’ mind because she didn’t care much for either of them.

At 16, Charlie tried to drive all the way to Mexico to escape home. Then, he almost married an exotic dancer at 17, but changed his mind at the last minute. Somehow he managed to escape all these escapades unscathed and even thrives as an adult. Not likely!


As mentioned, Charlie’s relationship with Alan is constantly strained. It’s a great source of comedy for the show, but it just doesn’t make sense. Charlie complains about the two guys living with him, but doesn’t do anything about it.

Charlie also had a relationship with his ex-sister-in-law – more on that later – just to spite Alan for marrying Judith. And finally, Charlie called Alan “selfish” for suggesting they skip a movie because Alan suffered a nervous breakdown. The list goes on and on, but it’s pretty clear that the producers wanted us to ignore how truly awful Charlie can be to Alan for the sake of comedy.


Way back in the season 1 episode “I Remember the Coatroom, but I Don't Remember You,” Charlie wanted to get back at Alan for marrying Judith. Charlie thought the best way to get revenge would be to be with Liz, Judith’s sister.

The strife continued when it was revealed that Alan asked Liz out before he was with Judith, and the whole scenario descends into chaos. Charlie isn’t exactly the best at solving conflicts, and his go-to to get back at people seems to be to have a relationship with someone they’re close to.


One night, Charlie had a relationship with an unknown woman and conceived a daughter. We didn’t see her in the beginning, so it seems like the only reason this was thrown into the plot was to make Charlie look like even more of a sleazebag.

Much later in the series – season 11 – we finally meet Charlie’s estranged lesbian daughter, played by Amber Tamblyn. But, considering Charlie is dead when she returns, it seems the only reason for her presence is to show that she turned out exactly like her dad. The whole estranged daughter thing seemed like an asterisk from the beginning and never really went anywhere in the end.


As we just mentioned, Charlie wasn’t much of a father to his daughter Jenny, so it didn’t make a lot of sense that whenever he sat down with Jake, he mostly doled out bad advice and tried to hook him up with older women – even though Jake was a minor for most of the series.

At the same time, he often criticized Jakes and the writers used their relationship as a source of humor. Charlie often talked down to his nephew, calling him a “dwarf” and telling him he was destined to be a fry cook. Considering his track record with women, Charlie was hardly the one who should be giving dating advice to anyone, let alone a kid.


Okay, so we do know that both Charlie and Alan’s relationship with their mother was strained growing up. After their biological father died when they were both very young, their mother dated other men and the boys ended up having three different stepfathers throughout their childhood.

Charlie had an especially hard relationship with her, as he left home a number of times as an adolescent and worried her (although, not too much, as we already mentioned). As an adult, Alan was surprised to find out that Charlie didn’t even have their mother’s number in his phone. Both men do everything they can to avoid her, and even though this is somewhat explained by their rocky childhood, we don’t really know what that’s carried into adulthood.


Jennifer Taylor and Charlie Sheen in Two and a Half Men

One of the things that have never sat well in Two and a Half Men is that Charlie somehow got into Julliard, a prestigious art school. We know that he drank, smoked, and ran away often as a teenager, so how is it possible that he was able to hunker down and study enough to get into art school? Sure, he writes jingles, but Julliard is one of the top schools in the country, so would that really be enough?

In any case, Charlie dropped out of Julliard to start doing his own thing. Obviously, the pressure and rigmarole of taking classes were too much for him at that point in his life. Nothing about Charlie’s personality, work habits, or appearance show us that he has the drive to be successful, but somehow, he is.


Musicians are typically a social bunch. They write, record, and genuinely enjoy performing in front of large audiences. No, you don’t have to be an extrovert to be a musician, but it certainly helps. Charlie, on the other hand, seems fine with being reclusive, often doing his own thing, not paying attention to anyone else’s schedule but his own.

One thing we know about him is that he has stage fright. If that’s the case, how would he have the courage to share his jingles with the world? After all, these are songs featured in commercials seen around the world. Sure, he doesn’t have to perform them in front of people, but playing them in front of groups of executives would be the first step to becoming a successful jingle writer. Something here just doesn’t add up.


Charlie Sheen in Two and a Half Men

After dropping out of school, Charlie moved back to Los Angeles with ambitions of becoming a film score composer, which seems like a tall tale given his lack of commitment to anything. Instead, he supposedly met a producer who was looking for someone to write jingles. Charlie wrote the fictional “Maple Loops” song, which made him a truckload of money.

Problem is, Charlie is rarely seen on the show actually working on anything. He always seems to have a ton of free time on his hands, but he’s never working out songs, writing lyrics, in the recording studio, or anything that has to do with producing music. Then, he apparently started writing children’s music under the alias “Charlie Waffles.” Hardly likely given his status as a nonchalant playboy.

9 HE’S WEALTHY BUT doesn't look like it

Bowling shirts and shorts. That seems to be Charlie’s go-to outfit, as he’s often depicted lounging around the house without anywhere in particular to be. He enjoys sleeping in, getting Berta to cook and clean for him, and generally not doing anything, as money seems to fall into his lap. Charlie rarely wears suits – or any designer clothing, for that matter - which doesn’t seem likely given his wealth and status in the entertainment industry.

Charlie never has to dress up for business meetings, dinners with clients or bosses, or collaborations with other entertainers or producers. He pretty much sticks to the thrift store shirt look no matter what the weather or the events of the day bring.


Two and a Half Men mostly takes place in Charlie’s house, but he’s constantly jumping relationships and therefore moving in and out as needed. In the early years, he dated Lisa and they lived in the house together. Then, there were times only Charlie lived there, or only Lisa lived there, or neither of them lived there.

In season three, Charlie decides to take off and marry Mia in Las Vegas, but breaks it off when she tells him she wants Alan to move out. Before his passing, Charlie runs off to Paris with Rose, where he’s reportedly hit by a train and dies – according to her, his stalker, at least. He’s later locked up in Rose’s dungeon but escapes after four years in season 12. Weird, to say the least.


This one is probably the most mind-boggling and unrealistic entry in this list. Most musicians live on the computer (and therefore, the internet), constantly using them to produce new music, promote releases and gigs, and build social media followings and buzz about their latest projects. As an entertainer, Charlie should be glued to the computer night and day, but the show tells us that he actually doesn’t even know how to use the internet.

Yes, there are artists out there that are old-school and prefer not to use computers for every aspect of their careers, but to suggest Charlie is insanely rich from music but that he doesn’t know how to use one is preposterous. Furthermore, he works from home, so how does that even make sense?


In the episode “I Can’t Afford Hyenas,” it’s revealed that Charlie knows almost nothing about his own finances. He uses an accountant to handle his daily living expenses because he’s incredibly irresponsible with money. When his accountant is arrested for stealing money, Charlie sees just how bad things have become – he’s on the verge of selling out because several of his accounts at the bank are delinquent.

It’s hard to believe that someone as rich as Charlie wouldn’t have the faintest clue where their money is or how it’s being handled. No, he’s not a very responsible person in general, but slackers usually know something about their own cash flow.


Charlie Sheen and Emmanuelle Vaugier in Two and a Half Men

In general, Charlie never has to live with the consequences of his actions. This is especially true when it comes to his relationships with women. For instance, Charlie ditches Mia (Emmanuelle Vaugier) in a recording studio after denying her advances and choosing to date Chelsea instead. He also gave Isabella herpes (as revealed at Charlie’s funeral), but wasn’t held accountable at the time.

Then, Charlie sleeps with Melissa in season six but then becomes annoyed when she starts hanging out around his house too much.There are way more examples to list here, but point is that Charlie rarely has to answer for himself when things go south.


Charlie’s relationships with women are constantly a revolving door. He’s a well-known womanizer who talks down to them, treats them like they’re disposable, and generally doesn’t want to be emotionally invested in them. But there’s one woman who he’s terrified of – his housekeeper Berta. His relationship with her doesn’t even make sense, as she’s always wise-cracking and ribbing him for everything.

As an employee, it’s assumed that Charlie pays Berta but at the same time, he’s scared of her. He makes sure not to piss her off, even though he doesn’t care about that aspect with any other woman. Berta keeps him in his place, which doesn’t really make sense since Charlie could theoretically fire her at any time.


Rose’s original far-fetched story about Charlie dying by getting hit by a train was pretty weak, but the rest of the backstory is just as bad, if not worse. Apparently, Charlie and Rose were in Paris for a few days when Charlie proposed to her. Rose said yes, but says she then caught Charlie in the shower with another woman. The next day, Charlie was supposedly standing on a platform when he fell and was struck by a train.

Of course, Rose’s story ended up being exposed as bogus in the end, but surely the writers could’ve come up with a better cause for Charlie when the real Charlie Sheen suddenly exited the show.


Obviously, this gag was meant to be ironic as Charlie supposedly spent so much time on his piano writing songs, but the idea that he was killed by a falling piano that was being transported through the sky is just plain dumb. Nobody in the real world moves pianos this way, and the “falling piano” trope has been used in comedy for years. It’s a bland and overused joke at this point.

Charlie Sheen’s somewhat sudden departure from the show left the writers scrambling, but for a while, it seemed they couldn’t’ decide on Charlie’s actual cause of death in the show. But the likelihood of actually dying from something falling from the sky is pretty minuscule, making this plot point lame at best.


Kathy Bates Ovarian Cancer

When Alan suffers a minor heart attack and ends up in the hospital, he sees a vision of a woman dressed like Charlie sitting at the foot of his bed. The woman (Kathy Bates) explains that she is actually Charlie, noting that he ended up in Hell after he passed away and his punishment was to live inside the body of a woman, for some reason.

At this point, Charlie Sheen was not welcome on the show, so the female storyline for Charlie seemed like something the writers rushed together. The producers of the show were impressed by Bates’ portrayal of Charlie but she didn’t end up staying on as long as they would’ve wanted.


Is there anything else about Charlie that doesn't make sense on Two and a Half Men? Let us know in the comments!

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