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  • Adorkable: Alan, especially in earlier seasons. While still "mourning" over his divorce, he often gets excited if something interesting happens.
  • Alternative Character Interpretation:
    • Is Alan's Butt-Monkey treatment uncalled for? Or is it Laser-Guided Karma for some unnamed act—or acts—of wrongdoing on his part before the show started?
    • Is Charlie just a bastard with a disregard with everything that isn't connected to himself and abusive to Alan for no reason? Or is he jealous of Alan because he was their mother's favorite when they were kids and acting out his unresolved frustrations?
    • Is Judith just a complete bitch for no reason, or is she lashing out after having actually been treated like crap by Alan and Charlie during her marriage to the former?
    • Did Evelyn merely insult and emotionally abuse Charlie and Alan growing up, or did she sexually abuse them as well? Is this the reason why they both hate women and treat every woman like a substitute Evelyn with whom they still wish to resolve their conflict?
    • Due to the actress, Jennifer Taylor, popping up several brief times in earlier episodes before she landed the Chelsea role, some like to play around with the idea that Chelsea's been stalking Charlie since season one.
  • Base-Breaking Character: Each of the lead male characters.
  • Big-Lipped Alligator Moment: The Sudden Musical Ending of "Grab A Feather And Get In Line."
  • Broken Base:
    • The show's quality after Charlie Sheen was fired. Most fans seem to agree that Season 9 (the first with Ashton Kutcher) is the show's worst season, as the writers were trying to find their feet again. Some regard the following seasons as an improvement, thanks to a major Retool in the cast and humor, while others regard them as being only slightly better than Season 9, and still way worse than the first eight seasons.
    • The series finale, hoo boy. Either you thought it was a great meta episode with some nice fourth wall jokes, or you hated it because of the constant Charlie Sheen bashing, and you feel Chuck Lorre needs to learn to just let things go. Or, you could be somewhere in the middle.
  • Character Shilling: Walden can't be in an episode without someone commenting on how damn pretty he is.
  • Creator's Pet:
    • Rose. Since her first appearance, she's had little depth than being Charlie's obsessive stalker and has never grown past that, but for some reason the writers continue to bring Rose back year after year and had the other characters claiming she was perfect for Charlie. Hell, by the end of season 8, she'd successfully manipulated Charlie over time into thinking she was the perfect woman for him, even though he had more reasons to think the opposite. Then she passed the Moral Event Horizon by killing Charlie, and not only does Rose get away with the murder, but a year later turns out to have started stalking Walden. And unlike Charlie, where she started stalking him because she couldn't let go of a one night stand, was doing so for no reason whatsoever.
    • Apparently, she never killed him. She only said she did so no one would search her house, since she's a good candidate for causing Charlie to go missing for a long time and had been revealed to have been keeping him in a deep hole in her basement, Hannibal Lector-style after he cheated on her while they were in Paris.
    • Walden. The writers loved bringing up how pretty he was every episode.
  • Designated Hero: Charlie and Alan can flip-flop to this because there's so much douchebaggery between them.
  • Designated Villain: Charlie sometimes gets hit with this whenever he and Alan are fighting. The best example is "All Our Leather Gear is in the Guest Room", Charlie may have been petty about it, but he has every right to not want bowls in his living room that he doesn't like. Instead, the show makes it seem like Charlie's in the wrong and he's forced to take back Alan.
  • Ensemble Dark Horse:
    • Berta is the one character on the show who almost everybody likes.
    • Russell the pharmacist.
    • Missi, due to being played by Miley Cyrus. Both of her episodes have been the season high for season 10.
    • Jenny, who was promoted to regular after one episode.
  • Fair for Its Day: Early episode "An Old Flame with a New Wick" has one of Charlie's exes coming out as a transgender man, and contains all the insensitive jokes one would expect of an early 2000s show dealing with transgender people. However, despite the initial shock, Charlie is rather quick to accept Bill for who he is and helps him adjust to his new life, which was quite progressive for its time. Similarly, the typically caustic Evelyn is in no way put off by Bill being transgendernote (though she was creeped out that he dated Charlie before transitioning), and continues dating him after he tells her the truth (albeit for typically superficial reasons).
  • Fanon Discontinuity: The post-Charlie seasons are disregarded by a lot of viewers. And even many who do like (or at least tolerate) the Walden seasons will ignore the series finale due to it turning Charlie Harper the character into a psychotic Jerk with a Heart of Jerk and the many fourth wall-breaking potshots at Charlie Sheen the actor.
  • Harsher in Hindsight:
    • Some of Charlie's antics have creepily become real, as in 2009, Charlie Sheen had to go to rehab for personal problems and his marriage took a turn for the worse and later ended in divorce.
    • Jon Cryer's ex-wife was reported to have hired a hitman on him. When Charlie asks Judith if he wanted Alan dead, this gives an odd dose of realism to the joke.
    • Also, Charlie once mentioned that he'd rather close his eyes permanently than give up alcohol. It was funny at first, until Charlie Sheen got kicked off the show due in part to his drunken antics and his character got Killed Off for Real in the series finale.
    • In an early episode, Charlie wakes up hungover and remarks that he's either extremely hungover or has been hit by a train. Subverted when it is revealed that Charlie didn't die from getting hit by a train.
    • In "A Pot-Smoking Monkey", Jake and Charlie discuss whether or not anyone will come to Charlie's funeral. When Charlie dies, his funeral is largely made up of angry ex-girlfriends who are there to either make sure he's dead or spit on his memory.
    • In "Working for Caligula", Alan jokingly remarks that Charlie will be the first of them to die.
    • All the jokes about Charlie's promiscuity and all those women who catch sexually transmitted diseases from him take a crazy dark turn when it's revealed that Charlie Sheen is HIV positive in real-life.
    • Seeing Jake score with an older woman in the Season 9 episode, “Not In My Mouth!” might seem cool in the context of the show. However, when you think about the fact that Jake lied about his age - she’d face dire consequences for having sex with a minor.
  • Hilarious in Hindsight:
    • Judith's bitchy antics post-divorce become this when her actress Marin Hinkle plays a traditional housewife horrified by her daughter's divorce and separation in The Marvelous Mrs. Maisel.
    • "Trust me, darling. I promise to stick around long enough to identify your bloated, gin-soaked, syphilitic remains."
    • A throwaway exchange from "A Pot-Smoking Monkey" takes on a whole new level of hilarity with the season 9 premiere:
      Jake: If you died, would any of those women be at your funeral?
      Charlie: As a matter of fact, a lot of them would. Granted, a few of them would just be there to make sure I'm actually dead.
    • The entire episode, "The Devil's Lube", where Charlie imagines what his own funeral would look like, and thinking he'll die unhappy, decides to marry Rose, of all people. Well...
    • In one episode, Charlie mentions to Alan that the only people Jake hangs out with besides them are military recruiters. Guess what happens to Jake at the end of Season 9?
    • When Angus T. Jones became a born again Christian and apologized for calling the show "Filth" the episode that aired shortly after the incident "I Scream When I Pee" had Jake proudly announce that he has the clap.. (And keep in mind Jake knew very well that he now has an STD but is proud that he has something "sexually transmitted".)
    • In Season 10, Walden pretends to be a poor man named Sam Wilson, and Alan scorns him for living a double life. In Season 11, Alan ends up doing the same thing by pretending to be Jeff Strongman.
    • For many seasons, it's believed Rose murdered Charlie. Melanie Lynskey, the actress who played Rose, got a new level of acclaim and recognition by playing a character on Yellowjackets who actually did murder her lover.
  • Ho Yay:
    • Parodied in one episode when Charlie and Alan pretend to be gay. Alan gets rather too into it, whilst Charlie repeatedly denies anything in that direction, naturally squicked due to the fact that they're brothers.
    • Alan and Walden keep ending up together, with one of them naked. And Alan had a "problem" in the morning.
  • Informed Wrongness: In one episode, Alan wants Charlie to let his girlfriend move in with them. Although Charlie is portrayed as unfair for refusing, he does have very good reasons for saying no: chiefly being that it isn't Alan's house - it's Charlie's, Alan contributes little if any financially, and Charlie is already letting Alan and his son Jake stay rent free. Of course, Alan still lets his girlfriend move in without telling Charlie, then holds a party without asking.
  • Les Yay: Kandi and Lindsey end up in bed together at the end of "I Scream When I Pee" when Kandi tried to convince Lindsey that Alan rejected her.
  • Memetic Mutation: Season 2 Episode 9's "Can You Eat Human Flesh with Wooden Teeth?" scene where Alan and Charlie left Jake behind is this with the series, being used as a meme template.
  • Moral Event Horizon: For Rose, it's killing Charlie, no matter how much of a jerk he was and how crazy she is.
    • "Of Course He's Dead" (the Grand Finale) revealed that Charlie did not die (although Rose did try to kill him) but was kept in a dungeon Buffalo Bill-style, which may still count.
  • Nightmare Fuel: The season 3 episode "Hi, Mr. Horned One" is really disturbing to watch as Charlie dates Isabella, a wild, sexually uninhibited, spooky, Satan worshipper.
  • No Yay: While a small (but vocal) minority of fans did legitimately ship Charlie and Rose, most viewers were deeply unsettled by their relationship and the eighth season's repeated rationalization of Rose's prolonged stalking and often violent and malicious behavior as "sticking by Charlie all these years". This, coupled with the fact that when they actually got their Relationship Upgrade, it was directly the result of Rose's machinations and they never spent even a moment of screentime as a mutual couple was the target of heavy criticism and actually could've conspired to end the show had the Retool not been necessitated.
  • Overshadowed by Controversy: For its first eight seasons it was seen as a fairly standard-issue sitcom — albeit one with an unusually high proportion of jerkasses among its characters — but nowadays it's virtually impossible to discuss the show without talking about Charlie Sheen's (and, to a lesser extent, Angus T. Jones') Creator Breakdown and subsequent exit.
  • Replacement Scrappy: Walden is seen by many as a poor replacement for Charlie, mainly because he wasn't Charlie, but also because Ashton Kutcher's comedy style just doesn't seem to fit in with the show, and his interaction with the other characters feels rather forced and unnatural.
  • Seasonal Rot: While many argue that it happened earlier in Seasons 7 and 8, due to the jokes becoming more juvenile and asinine and the three titular characters becoming more Flanderized, it is near-universally agreed that it was Season 9 that saw the show permanently go downhill. The ninth season, produced following the public meltdown and departure of Charlie Sheen, is largely considered this due to much worse writing and extreme Flanderization: Alan becoming more immature and an even bigger mooch, Jake smoking pot and becoming even more stupid, Rose becoming more a bitch, Lindsay becoming crazier, and Berta being the only character who stayed consistent. The tone is completely different, there's a much greater emphasis on Toilet Humour, and Charlie's replacement Walden is little more than a rich and more immature version of Alan and his interactions with the other characters feel very forced and unnatural. The remaining seasons improved somewhat by retooling the humor in a way that clearly took inspiration from The Big Bang Theory (which at least was more appropriate than the toilet humor, given that Walden was meant to be a technology mogul), but it never again reached the levels of popularity it had in Seasons 1-8, and eventually ended with a widely-reviled finale that mostly just took pot-shots at Sheen. To emphasize this point, every episode from the first eight seasons on IMDB is rated between 7.2 and 8.7, with every season having at least a couple highly rated episodes. Seasons 9-12 pre-finale, however, has every episode rated between 5.3 and 7.2. And of course, the finale episode crashes through the floor, rated 3.8.
  • Strawman Has a Point:
    • We are supposed to side with Rose, whom Charlie has thrown off like a fake dollar eight years ago, and her ruining Charlie's dates and stalking his ex-girlfriends ought to be Laser-Guided Karma punishment for his Casanova attitude. But Charlie is right; Rose has been ending her relationships. Jerkass as he is, he does tell the truth.
    • When Walden starts dating Rose in Season 10, Alan is treated as completely unreasonable for repeatedly telling Walden not to do so.
  • They Changed It, Now It Sucks!: Ashton Kutcher replacing Charlie Sheen, some fans are claiming that while he is a talented actor, he just doesn't fit into the show very well and comes across as a Poor Man's Substitute. Some people also feel this way about the new decor of the set.
  • They Wasted a Perfectly Good Character: Judith's sister, Liz, only appears for one episode, which can be seen as a huge waste of Teri Hatcher. There's a plot hook where it turns out that Liz was Alan's first choice before he got in a relationship with Judith, but it goes nowhere beyond that. It's especially odd that she doesn't even appear for the episodes surrounding Judith and Herb's wedding.
  • They Wasted a Perfectly Good Plot:
    • Charlie and Rose moving to Paris. It could have been left as resolution for their arcs while still removing Charlie from the show. Instead, Rose finds Charlie in bed with another woman and throws him in front of a train, then practically gloats about it, becomes The Artifact without Charlie and starts stalking Walden.
    • Mia's return was hyped up as a Cliffhanger to close out the Season 6 finale, but gets completely thrown out the window in the first episode of season 7.
    • For some, introducing Ashton Kutcher as a new character instead of The Other Darrin. It would have been a far better Take That! to Charlie Sheen than anything they actually ended up doing, and would have kept the show's original tone.
    • It's never conclusively answered as to whether Judith's daughter Milly is actually Alan or Herb's daughter. Most of the signs seem to point to Alan.
  • Too Bleak, Stopped Caring: To put it curtly, the casting crew is just a plain mess. The two main characters, Alan and Charlie, are hardly much different from the other selfish Jerkass characters on the show, which makes it confusing for the audience on who exactly they're supposed to be rooting for.
  • Wangst:
    • Alan. He often complains about how Charlie has casual sex and has a better life than him.
    • Charlie's reactions to Chelsea wanting a breast reduction surgery to deal with back pain are beyond absurd. He acts like it's the worst thing that could ever happen, and even cries over it!
  • The Woobie:
    • Alan. Pretty much the last few seasons consist of him getting repeatedly screwed over in some way, he was almost Driven to Suicide in "It's Like Working For Caligula", his son is quite possibly the most disrespectful and unappreciative teenager ever portrayed on an American TV show, his brother tends to be an asshole who mostly coasts by in life, his mother is an unrepentantly horrid Evil Matriarch that can't see any flaws in herself, his ex-wife is a bitch that said she'd rather die alone than be with him, the list just goes on and on. It's sad that Chuck Lorre really makes him a live action Meg Griffin.
      • Of course, some people see him as a Jerkass Woobie due to his sponging off Charlie while constantly criticizing every aspect of his life and biting the hand that feeds him, as well as his becoming a horrible father to Jake.
    • Charlie himself is a Jerkass Woobie. After all, he too grew up under the thumb of the same narcissist who drove his father into an early grave and constantly abused and neglected him and Alan their whole lives. Even as an adult, she still treats him like crap and has made him unable to ever have a meaningful relationship, which has often come back to bite him. Not to mention that his brother constantly mooches off of him and does nothing but criticize him. This is all Played for Laughs.
    • Jake is another Jerkass Woobie to some extent. Although he becomes an increasingly selfish Literal-Minded ungrateful dumbass over the course of the show, it's hard to blame his bitter attitude considering his mother thinks he's a burden and she and Alan both openly give up on him, stop caring and can barely tolerate him. While this is Played for Laughs, his life could have easily gone a different direction if his family gave a shit.
    • Walden Schmidt should count. His High School sweetheart told him she wants a divorce, which prompts him to throw himself into the ocean and try to drown himself, only to pull himself out because the water was cold. That's enough there.
    • And Herb. He's probably the nicest and most decent guy in the whole show, and suffers all kinds of abuse from Judith, not to mention his daughter Milly might not even actually be his. Ramped up to eleven after Judith divorces him.
    • Whenever we're reminded of Louis' life as a foster kid. Especially on Christmas!

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