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

Charlie's Sheen character on Two and A Half Men isn't exactly likeable. Here are just 10 of the worst actions he has taken on the long-running sitcom.

Not all sitcoms age well, especially not Two and a Half Men. Even in its heyday, the raunchy comedy that chronicled the shenanigans that Charlie (Charlie Sheen) – later replaced by Walden (Ashton Kutcher) – his brother Alan (Jon Cryer) and nephew Jake (Angus T. Jones) got into was criticized for being juvenile, insensitive, and even downright misogynist. The more scandalous moments only got worse over time, with some saying that it’s impossible to watch the sitcom today without cringing.

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Charlie, the focal ladies man in the show’s first half, could be found at the center of most if not all of the show’s controversy, both on and off camera. As a playboy, his questionable chauvinist shtick only got worse with the benefit of hindsight and retrospective analyses. In honor of Charlie’s sleazy legacy, here are his 10 worst moments from Two and a Half Men.

10 Charlie Belittles His Past Girlfriends (Season 7, Episode 21)

To deal with his insomnia, Charlie smokes some medical marijuana to help him sleep. During one of his trips, he’s visited by all of his ex-girlfriends who each verbally tear him a new one.

Rather than listen, he dismisses their complaints and condescends on some of them, angry that they’re angry at him. While this gets a slight past since Charlie was under the influence of drugs, his flippant attitude towards his exes was still undeniably rude. It’s quite likely that he would’ve said the same things or worse were he not smoking weed.

9 Charlie Insults Chelsea Out Of Breast Reduction Surgery (Season 7, Episode 6)

Following Alan’s suggestion, Chelsea decides to undergo breast reduction surgery to alleviate her back pains. Fearing that he would lose what turns him on, Charlie flies into a rage, temporarily kicks Alan out of the house, and berates Chelsea for even thinking about the medical procedure.

Charlie convinces her to forego the surgery by saying that a reduced bust size would make her butt more noticeable. Nearing tears, Chelsea complies with Charlie’s demands. All of this is framed as a major win for Charlie and nobody else.

8 Charlie Thinks About Rape (Season 6, Episode 16)

During the earlier seasons, Charlie’s feelings for Chelsea develop and the two eventually decide to take things seriously. But despite his newfound commitment, he still has to be convinced by Alan not to have sex with the unconscious, half-naked woman on his bed.

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It takes him the entire episode to realize that he may be in fact a “sleazeball” for even considering the idea of taking advantage of a sleeping stranger – a supposedly humorous dilemma that would be mercilessly savaged today. Also, all of this happens while Chelsea is attending her mother-in-law’s funeral.

7 Charlie’s Terrible Breakup Gambit (Season 5, Episode 10)

While trying to console Jake after his first breakup, Alan discovers that his high school girlfriend Charity cheated on him with Charlie. Enraged, Alan decides to avenge his wounded pride by stealing Charlie’s current girlfriend Gabrielle.

In truth, Charlie was planning to split from Gabrielle but never had the guts to tell her, so he let Alan woo her. He even compares sleeping with a now depressed Gabrielle to necrophilia before revealing to Alan that he’s dating Charity again. What makes everything worse is the way the episode gives Charlie the high ground despite him never regretting his actions.

6 Charlie Teaches The Virtues Of Cheating (Season 7, Episode 11)

When Jake’s girlfriend Celeste goes home for the holidays, Charlie figures it’s the perfect time to teach his nephew about the manly ways of cheating. He even teaches him how to keep the third party a secret, believing that Jake’s too young to think about getting tied down or committing to his significant other.

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This backfires spectacularly when Celeste returns, hoping to surprise Jake with an early Christmas gift. The ensuing break-up leads to everyone getting pissed at Charlie but as per series tradition, it’s treated as a punchline rather than an indictment.

5 Charlie Gives STDs To Many Women (Season 9, Episode 1)

Even in death, Charlie found a way to piss off everyone around him. During his closed casket funeral services following his apparent death via train to the face, a group of women he slept with in the past charge in and make his many wrongdoings known.

Chief among these is the long list of Sexually Transmitted Diseases (STDs) he gave them. It’s made clear that he never told them about his STDs, which justifiably enraged them. Because of this, no one – not even Alan – had anything nice to say about him during his wake.

4 Charlies Cheats On Rose During Their Honeymoon (Season 12, Episode 15/16)

After years of being stalked by Rose, Charlie settles down and ties the knot with her. Not only is the marriage’s foundations questionable at best, but what happens afterwards is beyond problematic.

Rose reveals that she caught Charlie cheating on her with an escort, a mime, and a goat in the shower. Charlie was always a playboy, but immediately cheating on his wife – plus engaging in bestiality – during their honeymoon was low even for him. This makes his captivity in Rose’s basement somewhat deserved, though it’s hard to forget that Rose is a dangerous psychopath.

3 Charlie Returns To Kill His Brother (Season 12, Episode 15/16)

After escaping Rose’s basement, the first thing Charlie decides to do upon finding out that Alan moved on with his life was to kill him. This despite the fact that Alan was under the impression that his brother really died four years ago.

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He also threatens Walden for essentially replacing him, sending him death threats and delivering sinister packages to his former housemates and friends as a warning. Even ignoring the behind-the-scenes issues that created this problem, Charlie’s sudden switch from oblivious jock to obsessive and murderous stalker wasn’t just uncalled for but downright deranged.

2 Charlie’s Off-Screen Meltdown

It’s impossible to separate Charlie Sheen from his televised persona and this showed up in the worst ways possible. As the seasons progressed, Charlie got progressively drunker and forgot his lines, slurring his way to a take’s end.

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All of these stem from Charlie’s actual personal life falling apart, which led to numerous problems like alcoholism, drug relapse, unjustified demands for a raise, and intense on-set fights with showrunner Chuck Lorre.  Things got so bad that the studio fired Charlie and killed off his character – both of which somehow made Charlie’s already public meltdown even worse.

1 Charlie’s Death (Season 12, Episode 15/16)

The only thing worse than the circumstances behind Charlie’s exit was his onscreen death. After a long absence, Charlie returns (via body double) in the series finale to be crushed by a piano. The camera pulls back to reveal Lorre, who mocks Charlie’s “Winning!” catchphrase before being crushed by another piano.

Granted, both the fictional and real Charlie aren’t the best people to have around but the finale doesn’t just show open contempt for him but for its audience as well. After teasing Charlie’s comeback, all long-time fans got was a smug comeback to a years old controversy.

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