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Two And A Half Men: The 10 Worst Things Alan Has Ever Done, Ranked

Two and a Half Men, the Chuck Lorre sitcom that spanned 12 seasons, ended a few years ago on a less-than-high note. But that doesn't mean it's been forgotten, especially since it often came under controversy for the various themes it portrayed, as well as some behind-the-scenes controversies with the notorious actors. Charlie Sheen is one of the most well-known examples.

Some of those on-screen controversies related to one of the two and a half men themselves, Alan. Alan Harper is arguably a terrible person. For many reasons. In fact, the majority of the people on Two and a Half Men are terrible people. Some may have redeeming qualities, but ultimately, there are few we really feel empathy for. Maybe Herb, or Jake when he's young and innocent. But definitely not most of the (adult) main characters.

We know that Charlie isn't a good person. That's kind of the whole shtick with his character. But many people who watched the show were quick to realize he wasn't the only one with some bad ideas up his sleeve. Here are all of the most terrible things Alan Harper has done, ranked from absolute worst to less terrible (but still not good).

RELATED: Two And A Half Men: 10 Questions About Rose, Answered

10 SCAMMING HIS FAMILY AND FRIENDS

Two and a Half Men Alan Harper ponzi scheme

In season eight, episode 16, "That Darn Priest," Alan runs a Ponzi scheme. Alan initially gets investments from the people in his life to finance an ad campaign for his business. But this soon turns into a Ponzi scheme and he ultimately scams everyone out of a lot of money and keeps it for himself. We're talking thousands of dollars from his family and friends, and the guy is barely feeling guilty about it. Eventually, Rose finds out about his scheme at the same time that Alan finds out about her fake mannequin husband. Rose offers to help by giving him money to pay everyone back in exchange for keeping her secret. But Alan suddenly becomes a good person again by saying he doesn't want to lie to Charlie.

9 USING CHARLIE'S RING TO PROPOSE TO KANDI AFTER THEY BROKE UP BECAUSE OF HIM

Two and a Half Men Alan Harper and Kandi

In season three, Charlie is engaged to Mia and Alan and Kandi are set to be the best man and maid of honor. However, Charlie calls off his wedding to Mia, perhaps one of the only women he ever actually loved, because of Alan.

RELATED: Two And A Half Men: The 10 Worst Things Charlie Has Ever Done

He finds out she wants to kick Alan out and ends up calling it all off for his brother's sake. Of course, Alan doesn't know this, but what he does next is still despicable regardless. Alan decides to use the ring Charlie had given to Mia to propose to Kandi, instead of just buying his own engagement ring.

8 CHEATING ON HIS GIRLFRIENDS BUT CRITICIZING CHARLIE FOR BEING A PLAYER

Two and a Half Men Alan Harper and Lindsey

For a guy who is constantly ripping on Charlie for being a player, Alan isn't that innocent himself. First, he cheats on Melissa, the one girl who may actually genuinely care about him, with her own mother. Eventually, he finally finds a good relationship with Lyndsey, but he cheats on her, too. With Melissa. After moving in with Lyndsey, Alan reunites with Melissa and they begin an affair, with Alan meeting her at Charlie's house without her knowledge that he doesn't live there anymore.

7 SLEPT WITH HIS GIRLFRIEND'S MOM

Two and a Half Men Alan Harper and Melissa's mom

Speaking of Alan's willingness to cheat on his girlfriends, the worst one yet was probably when he slept with Melissa's mom. In season six, episode 14, "David Copperfield Slipped Me a Roofie," Alan is upset with his family and Melissa invites him to move in with her. Melissa also lives with her mom, Shelly, who is a massive hippie pot smoker.

RELATED: The 10 Worst Episodes Of Two And A Half Men (According To IMDB)

Shelly gives Alan some banana bread laced with pot and he ends up sleeping with her. Now, anyone who has ever eaten an edible in their life will know this isn't really an excuse to sleep with your girlfriend's mom.

6 ENTERING A FAKE GAY MARRIAGE WITH WALDEN TO ADOPT A BABY (AND THEN DATING THE SOCIAL WORKER)

Two and a Half Men Alan Harper and Walden marriage

This one is just insulting and terrible. In the final season, Walden decides he wants to have a baby, but seemingly can't adopt one on his own (even though he's a billionaire). So, Alan and Walden decide to enter a scam gay marriage so they can adopt a baby named Louis. However, not only is this whole plotline offensive, it's absurd as well. Ms. McMartin, the social worker assigned to Walden's case, figures it out when she ends up dating both Alan and Walden at one point. They still get the baby after all that.

5 SLEPT WITH JUDITH BEHIND HERB'S BACK AND CONVINCED HIMSELF HE'S THE FATHER OF THEIR BABY

Two and a Half Men Alan Harper and Judith

We just need to make a note here. Herb may be the real hero of the show. The guy puts up with so much from everyone around him and just tries to keep a smile on his face the whole time. Anyway, in season six, Judith becomes pregnant. The timing is iffy because she had recently cheated on Herb with Alan. Yet another relationship Alan doesn't respect and tries to destroy.

RELATED: 10 Jokes From Two And A Half Men That Have Already Aged Poorly

So, Alan becomes convinced it's his baby and tries constantly to get her to drop Herb and take him back to be a family. When little Milly is born, it's never revealed who the real father is. But the way Alan deals with it and tries to break up their marriage when Judith constantly tells him to stop is not a good choice on his part.

4 FREELOADING OFF CHARLIE FOR YEARS

Two and a Half Men Alan Harper and Charlie

Despite the fact that Alan has a good job as a chiropractor, he leeches from Charlie and acts as if he has no other option and couldn't live on his own. However, the reality is that Alan can afford his own place, but it wouldn't be a nice beach house like Charlie's. So, ultimately, he'd rather sponge off his brother to live in a nice Malibu home than be an independent man living on his own and making his own way. That's a pretty terrible personality trait.

3 WHEN CHARLIE DIES, HE FINDS ANOTHER RICH PERSON TO FREELOAD OFF

Two and a Half Men Alan Harper and Walden

It's not bad enough that he still hasn't found his own way once Charlie dies. He then proceeds to find another rich dude to mooch off, Walden. Somehow, he convinces Walden it would be a good idea to let him and Jake continue freeloading and living in the beach house.

RELATED: Two and a Half Men: 10 Storylines That Were Never Resolved

In what world would this actually happen? Basically, this guy just goes from one rich dude to another to make sure he always gets a cushy lifestyle without the price tag.

2 WINS HALF A MILLION DOLLARS AND BLOWS IT ALL IT ON KANDI

Two and a Half Men Alan Harper and Kandi in Vegas

Alan's entire shtick is that he's constantly broke and can't make it on his own. Despite having a chiropractic practice. So, when he finally catches a break and wins $500,000 at the casino, you'd think he would finally use that money to get himself a life. He could pay Charlie back, or buy his own place for them to live. But instead, he spends it all on Kandi, who soon wants a divorce anyway.

1 USING HIS SON TO MAKE HIMSELF LOOK SUPERIOR

Two and a Half Men Alan, Charlie, and Jake

The entire time Alan is freeloading off Charlie, he's also bringing his son there on weekends and then expecting Charlie to go out of his way to change his lifestyle for Jake's sake. When Charlie gets caught doing something inappropriate around Jake, Alan always uses it as a moment to make himself look and feel superior by being the "good guy." In reality, it's probably Alan who is a worse influence on Jake because Jake sees him freeloading for his entire life.

NEXT: Myers-Briggs® Personality Types Of Two And A Half Men

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