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Two And A Half Men: The 10 Worst Things Charlie Did To Alan

There’s no chemistry between characters in sitcoms unless there haven’t been times where they drive each other crazy, but Two and a Half Men almost exclusively relied on Charlie Harper’s ill-treatment of his brother Alan for the first eight seasons. 

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Some of the things Charlie did to Alan would make you wonder why Alan ever put up with him, but perhaps we need to accept that Alan really saw staying at beach house worth taking all the abuse Charlie threw at him. For you to understand all the horrible things Charlie did to Alan, here are 10 of the worst from the lot.

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10 Leaving Alan Out Of His Will

Charlie received a visit from his long-time friend in Season 6, who proceeded to die right then and there as a result of his corrupted lifestyle. This made Charlie reflect on his own life decisions, where he imagined an elated Alan at his funeral because he got everything Charlie had owned.

Once Charlie was snapped out of this fantasy, he set about to make amends with everyone in his life - everyone not named Alan Harper that is. By the end of the episode, Charlie is shown making his new will, where it was heavily implied that Alan wouldn’t get even a cent upon Charlie’s death.

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9 Fooling Around With Alan's Assistant

Charlie had a tendency to snag any attractive girl he laid his eyes on, with Alan suffering from the consequences of these actions. It took Alan a long time to find a competent receptionist for his business, but Charlie ruined that by hooking up with her.

This led to a weekend of fun for Charlie, where Alan’s repeated pleas for him to not get involved with the receptionist were totally ignored. When Charlie inevitably dumped her, Melissa took her wrath out on Alan instead. Now, the already broke Alan had to pay her multiple times more the salary she was originally making, along with suffering from Melissa’s seemingly dangerous anger.

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8 Keeping Alan Away From His Friend Group

Even though Alan likes to think he’s got the higher ground on Charlie, the truth is that nobody really likes him. He has no friends or social life of his own, with his own brother trying his best to keep him out of his own group.

However, Charlie was pretty hurtful when he told Alan to get lost while he had his big shot buddies over (one of them being Sean Penn of all people), and even Charlie’s celebrity pals felt bad enough for Alan that they wanted him to join them. After he begrudgingly let Alan in, Charlie tried his best to keep putting him down in front of the rest of the group.

7 Chastising Alan For Living With Him

This was a trait of Charlie that never went away through his whole time on Two and a Half Men. He only let Alan live with him out of the moral obligation that came with being his brother, not because he actually wanted his brother there. 

And it’s not like Alan didn’t pay in some way to live with Charlie, as the latter’s incessant jabs at Alan for staying at his house could be considered a form of payment. After all, Charlie would bring this fact up everyday and made a joke out of it to annoy and belittle Alan.

6 Ruining Alan's Wedding

Since Alan never had any friends of his own, he had Charlie as the Best Man at his wedding to Judith. This didn’t work out to anyone’s benefit as Charlie couldn’t care less about the event. 

Charlie’s entire contribution toward his brother’s big day was to be totally out of line as he got together with Judith’s little sister while the wedding reception was still going. He would then take the microphone while being intoxicated and sing “Super Freak” right into Judith’s face; it’s no wonder Judith hated him, and just like that Alan’s wedding was ruined.

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5 Go Around Telling Everybody Alan's A "Sponge"

Charlie claims he’s too embarrassed to tell anyone about Alan, but the truth is he does just that; too bad that none of what he says is any good. We’ve seen this on many occasions where Charlie’s friends and acquaintances visit and are already aware of Alan and his “sponge” reputation of mooching off Charlie. 

In one episode, all Charlie’s friend had to do was take one look at Alan and then ask Charlie if Alan was the sponge in question; Alan had no chance of coming across as someone better because Charlie would set him up like a sponge in the minds of others before they met Alan.

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4 Making Fun Of Alan In School

Two and a Half Men did show a lot of moments where Charlie and Alan behaved like true brothers, but all of these were restricted to when they were older, because all of Alan’s childhood memories comprised of him being antagonized by his brother.

Charlie admitted Alan was right when he claimed his entire school life went away with Charlie ganging up on him with the rest of his school friends and making fun of him. This led to Alan being friendless around this time, a sad fact that is wholly Charlie’s fault.

3 Being Responsible For Alan Having No Money

You’re fighting a losing battle if you’re trying to keep Charlie from hooking up with an attractive woman, because no force on Earth has been shown to be capable of preventing that from happening.

Alan got the worst out of this, though, when Charlie had an affair with his lawyer, breaking up with whom resulted in Alan’s life becoming hellish. When Charlie broke up with the lawyer, she went on ahead to get revenge by forcing a deal in Alan’s divorce with Judith, where the latter ended up getting over $4,000 in monthly alimony along with child support and everything valuable there was in their household. After that, Alan was permanently left without money.

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2 Bullying Him In General

There didn’t ever seem to be a real relationship between these two brothers, and it appears their dynamic entirely comprised of Charlie bullying Alan while the latter took it. It didn’t matter that the men were no middle-aged because Charlie was still seen giving Alan wedgies.

Whenever Charlie was feeling down, his go-to idea would be to let his frustrations out on Alan and take away certain privileges that came with staying at the house. Even at Alan’s birthday party, all Charlie did was demean Alan in front of the others because then the party seemed like fun to him.

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1 Trying To Kill Him

Charlie did some horrible things to Alan, but the most perplexing one remains his constant death threats to his brother in the series finale. It made no sense either as to why Charlie would want to kill Alan, seeing as Alan had kept the beach house with him even when he’d thought Charlie had died.

Charlie ended up paying everybody huge sums of money when he was freed from Rose’s captivity, but Alan was his target for some misplaced vengeance we have no clue how he justified in his head. Whatever he thought Alan did, wanting to kill his own brother was easily the worst thing Charlie ever wanted to do.

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