A list of characters and associated tropes in the long-running sitcom ''Series/TwoAndAHalfMen'':

[[foldercontrol]]

[[folder:The Harper Family]]

!!! Charles Francis "Charlie" Harper (Creator/CharlieSheen)
* TheAce: At least compared to Alan. Women and money just fall into his hands!
** BrokenAce: There are some moments where Charlie's vices catch up with him (at least until he was killed).
*** In fact, the entire original premise of the show is that Charlie is one of these because Alan and Jake came back into his life.
* AdamWesting / MetaCasting / WriteWhoYouKnow: Charlie Harper is basically Charlie Sheen without the "Sheen".
* TheAlcoholic: Gradually over time, mostly in the later seasons, where if he's home, he's either pouring himself a drink or has one in his hand.
* AlwaysSomeoneBetter: To Alan.
* AndThereWasMuchRejoicing: Next to no one had a single nice thing to say about him during his funeral (Alan ''tried'').
* AnythingThatMoves:
--> (after Charlie's weekend with Melissa does not end well)
--> '''Alan:''' You sure you don't want to come down to my office and hump my ''fax machine''?
--> '''Charlie:''' [[ComicallyMissingThePoint You still have a fax machine?]]
* AshesToCrashes: Ultimately, his smoldered ashes end up on the floor of the house when Alan drops them after being startled by Walden. And again when Jenny shows up.
* AssholeVictim: The women who attend his funeral certainly think so. Whether or not he was is up for interpretation.
* AtLeastIAdmitIt: Whatever flaws Charlie has, he doesn't deny who he is.
* BackFromTheDead: [[spoiler:If what happened in the finale makes any sense.]]
* BastardBoyfriend: To Chelsea. When she was suffering back pain due to large breasts he tried to [[ItsAllAboutMe prevent her from having breast reduction surgery so that she'll stay attractive to him.]]
* BenevolentBoss: Most of the time to Berta, he paid her well and at the wake after his funeral, Berta says she was the best boss he ever had.
* BigBrotherBully: To Alan, in their childhood.
* BunnyEarsLawyer: Gets paid millions just for writing jingles and doesn't have to do any other actual work or support anyone else. This is one of the main reasons why Alan despises him so much.
* TheCasanova: Sleeps with a woman every other episode (if not more).
** And it's one of the traits passed down from father to daughter.
** KidAnova: Was one of these in his youth as well.
* CasualKink: According to one of the women at Charlie's funeral, he liked being spanked while wearing her panties.
* TheCharmer: For all his flaws, Charlie actually does treat the women he sleeps with rather well. And then after the sex...
* TheChewToy: He does have his moments as a result of getting hit with the IdiotBall, such as the time when he thought his ex-girlfriend's son was his own. HilarityEnsues.
* CharacterDevelopment: Charlie may have been an immature narcissist and so forth, but he did learn how to be a better uncle and more willing to be in a monogamous relationship. [[{{Flanderization}} Unfortunately it was thrown out the window in later seasons.]]
* ChickMagnet: Alan put it best, ''"They just drop out of the sky for him!"''
* ComedicSociopathy: To disturbing levels.
* CoolUncle: To Jake, at least originally. Maybe subverted in the series finale, where he sends Jake a check for $25,000.
* DeadpanSnarker: One of the biggest, if not ''the'' biggest, on the show.
* DeathBySex: Rose catches him showering with another woman during their vacation to Paris and pushes him in front of a train. [[spoiler: However, this was subverted in the finale: Rose actually kept him locked up in her basement for four years.]]
* DepravedKidsShowHost: "Is There A Mrs. Waffles?"
* DisappearedDad: He decided that he didn't want to be in his daughter Jenny's life anymore and just sent child support.
* DreadfulMusician: He can definitely play the piano well, and turns out to have a surprising proficiency for writing childrens' songs, but most of his actual jingles are so bad that it makes you wonder how he was ever able to make a living (to say nothing of a living in ''Malibu'') off of it.
* [[spoiler:DroppedABridgeOnHim: A train, more specifically. In the finale, a piano... [[GainaxEnding sort of.]]]]
* DudeWheresMyRespect: His family does nothing but insult him, his career and his lifestyle despite him being incredibly successful as a musician (The quality may be questionable, but he's still really successful.) and having every right to live his life as he sees fit.
* EvenTheGuysWantHim
* EveryoneHasStandards: Charlie found there were lines even he wouldn't cross, such as in the Christmas episode where he refused to sleep with a woman that was possibly his sister. As Rose quipped, "It's a Christmas miracle!"
** He also refuses to sleep with teenage girls, as shown with his refusal of Berta's granddaughter's (played by Creator/MeganFox no less) advances.
* FoolishSiblingResponsibleSibling: The Foolish to Alan's Responsible.
* [[FourTemperamentEnsemble Five Temperament Ensemble]]: Choleric.
* {{Flanderization}}: Charlie became an even heavier drinker and an even bigger {{Jerkass}}. Was flanderized into a hard drug user after his death, though this may have been part of a large TakeThat aimed at Charlie Sheen.
* GenreSavvy: Only when it comes to Alan though. As Charlie says, he can read Alan like a stop sign.
* GirlOfTheWeek: One has to wonder at times how Charlie Harper is the less-exaggerated version of the actual Charlie Sheen.
* HandsomeLech: Charlie's the kind of guy who would be in the dictionary under "man-whore" if the word was in there. It's made all the weirder by the fact that he writes children's songs for a living.
* HilariouslyAbusiveChildhood: As he tells to Evelyn, when she asks why doesn't he like her:
-->I'm not saying I hate you, but if I did, it might have something to do with the fact that you're a narcissistic bloodsucker who drove my father into an early grave, after which you married a succession of men who couldn't care less about Alan and me, which was just fine with you 'cause you... looked at us like a couple of dancing monkeys you could just haul out whenever it suited you! And when it didn't, you sent us off to boarding school or camp or that kibbutz in Israel, where we got beat up 'cause we weren't even Jewish! And now... now you show up here every chance you get to lay a guilt trip on me for not appreciating my cold, lonely, loveless childhood!
* InstantSeduction: Mia was the only one this didn't work on.
* ItAmusedMe: His reason for picking on Alan so much.
* ItsAllAboutMe: He's so self-obsessed that when Alan was suicidally depressed all he was thinking about was how Alan's outburst embarrassed him.
* {{Jerkass}}: A selfish, egotistical, and narcissistic womanizer.
** JerkassFacade: And although he would never admit it, he enjoyed Alan and Jake's company.
** JerkWithAHeartOfGold: In particular, his relationship with Chelsea brought it out. He also really did care about Alan, Jake, and even Evelyn.
** JerkWithAHeartOfJerk: Following Charlie Sheen's dismissal from the show, the writers throw the above under a bus as well. The finale especially tries to drive the point home that Charlie really was a drug-addled, uber-violent asshole, with Alan and Evelyn frightened by the thought that he might actually try and kill them.
* JustFriends: With Lyndsey, despite what Alan thought.
* KarmaHoudini: Charlie's jerkassery never seemed to catch up to him until he was McLeaned at the beginning of Season 9.
** LaserGuidedKarma: The girls who attend the funeral seem to view his death as this.
* KavorkaMan: He's a millionaire with a beachhouse; it's just his personality that makes women leave him.
* KilledOffForReal: Between Seasons 8 and 9, (presumably) by Rose. Subverted in the series finale.
* LackOfEmpathy: Whenever people around him suffer he will often [[EvilHasABadSenseOfHumour laugh in their face about it]]. At one point, his girlfriend was having back pain due to large breasts and he tried to prevent her from having breast reduction surgery to deal with that problem. He's even been known to [[ManipulativeBastard take advantage of people's emotional and social problems]] for his own benefit.
* LadykillerInLove: With Mia, Chelsea, and Rose. They were the only women he ever proposed to, but never married either of them (and, in the latter's case, never ''lived'' to marry).
* LovableSexManiac: Subverted. It caused a lot of resentment from [[HollywoodDateless Alan]] and [[EvilMatriarch Evelyn]]. Jake was cool with it though.
* ManChild: "You are a ''child''! A high maintenance ''child''!"
* MommyIssues: Even more so than Alan.
* {{Narcissist}}: Charlie is ''always'' thinking of himself and has a massive ego. When others around him suffer he [[EvilHasABadSenseOfHumour finds it amusing]] but then expects them to sympathize with him whenever he suffers.
* NoodleIncident: Most of Charlie's sexual escapades, especially the ones before Alan and Jake move in.
* NotSoDifferent: Has shades of this when it comes to Evelyn. They're both narcissists, drink a lot and are promiscuous. Alan has linked some of this to a possible OedipusComplex.
* NotStayingForBreakfast: Charlie's specialty. His night usually goes like this: he meets a girl, sweet-talks her, takes her home, suggests they go upstairs, has sex with her, and is gone before she wakes up. A lot of the time, he doesn't even know the girl's ''name''.
* OddCouple: With Alan.
* OneOfTheKids: According to Alan - ''"You're a child! A high-maintenance child!"''
* OneHourWorkWeek: Seriously, how often do you ever see him actually working or going somewhere related to his job? Not very often.
** Somewhat justified, since the show tends to take place on the weekend and Charlie chose his line of work since he can do very little work for a lot of money.
* ParentalNeglect: Scorns Evelyn for this particular reason.
* PlatonicLifePartners: With Berta. WordOfGod is that they're best friends, but neither would admit it.
* ThePornomancer: His talent of instantaneously bedding women borders on the supernatural, to say the least.
* PutOnABusToHell: Literally. "Why We Gave Up Women" in Season 9 reveals that Charlie has been consigned to Hell to spend eternity in a woman's body (and a pair of testicles hanging from his lady parts).
** BusCrash: Charlie never left the show, but after it continued with Season 9 (following the hiatus that ended Season 8), Charlie was dead in the opening episode.
** TheBusCameBack: And returned in the series finale, for all of about 10 seconds.
* ReallyGetsAround
* RealLifeWritesThePlot: After his falling out with Chuck Lorre, Sheen's Character is killed off in a very unglamorous way and manages to undo his potental CharacterDevelopment in the Trip he took with Rose at the end of Season 8.
* SmugSnake: Mostly towards Alan, whenever he's bragging about his latest conquest.
* StylisticSuck: His jingles.
* TheNicknamer: Mostly to Alan, Jake and Evelyn. Alan was "The Sponge", Jake was "Numbnuts", "Tater head" and "Pumpkin head" and Evelyn was "Satan".
* TookALevelInJerkass: Goes from caring about Alan and Jake in his own way to screwing with them just for the hell of it.
* UnproblematicProstitution: Has an entire contact list full of hookers on his phone.
* UnsympatheticComedyProtagonist: Most of the time.
* VitriolicBestBuds: When he wasn't fighting with Alan or Evelyn, they were this.
* WhatDidIDoLastNight: This is a weekly ritual for him.

!!! Alan Jerome Harper (Jon Cryer)
* AbhorrentAdmirer: He attracts old women, like Judy's or Melissa's mother.
* [[AbusiveParents Abusive Parent]]: To Jake, starting with Season 6.
* {{Adorkable}}: Specially in earlier seasons. While still "mourning" over his divorce, he often gets pretty much excited if something interesting happens.
* AesopAmnesia:
** After Walden's ploy to find a woman by pretending to be someone he's not completely blew up in Walden's face, despite Alan's warnings, Alan seems to have completely forgotten these events ever happened in Season 11 and pursues Lyndsey and her fiancée's sister, Gretchen, using the false identity of "Jeff Strongman."
** Charlie's "death" clearly did not make Alan realize that your bad deeds will catch up with you, as he (Alan) becomes completely irresponsible and immoral during the later seasons, essentially becoming the kind of person he scorned Charlie for being earlier on.
* BecauseYouWereNiceToMe: He falls in love with Charlie's older, motherly girlfriend in one episode for this reason.
* BitchInSheepsClothing: Alan is the kind of guy who has spent his whole life living by an arbitrary morality, and is now mad that he hasn't reaped the rewards he thinks he deserves for it. Yes, [[ButtMonkey life hasn't treated him all that well]], but a lot of that is because Alan is a spineless doormat; he is incredibly resentful against his brother, who lived in hedonistic revelry that Alan secretly wanted himself, but never allowed himself to go for because he thought that the universe would automatically reward him for his passive aggressive nice guy act. In the last few seasons of the show, however, he seems to have realized this, and consequently has relinquished all pretenses of being a NiceGuy.
** NotSoDifferent: Alan likes to act like he's better then Charlie because he got married and had a kid instead of having endless casual sex in various ways, but while he doesn't have as much sex as Charlie(or with as many women), Alan has quite a bit of casual sex and has cheated on women several times and done some other morally questionable stuff throughout the series.
* BornUnlucky: Despite all his faults, one cannot deny that Alan was born with some kind of curse hanging over his head.
* ButtMonkey: Try and name one episode where something bad doesn't happen to Alan in some way. Go ahead, try it.
** Though things have turned around for him in the later seasons, even if he doesn't fully appreciate it. And it's implied that Alan gets to stay in the beach house forever, since Walden is in fear of spending his senior years alone.
* TheCassandra: He repeatedly warns Walden about Rose, and is eventually proven right.
* CampStraight
* ChildhoodFriendRomance: With Judith. Ends terribly.
* CosmicPlaything: Just about ''everything'' is out to get him, and is merciless in execution.
* CovertPervert: Although he tries to act more controlled than Charlie when it comes to women, Alan is perhaps even more of a pervert.
* TheDandy: Primps about his clothing fairly often.
* ADateWithRosiePalms: Very often. Charlie's even caught him having sex with a vacuum, he admits to masturbating before dates to get the right enthusiasm out of women, and once masturbated seven times in several different locations just to use up pills before they expired (eventually getting arrested when he was caught in a movie theater).
* DeadpanSnarker: Towards Charlie.
* {{Deuteragonist}}: From Seasons 1-8.
* ExtremeDoormat: Has consistent bad judgement, and had to pay alimony to Judith until she got remarried.
* FailureIsTheOnlyOption: No matter what happens, Alan will always end up living in the beach house again, broke and without a girlfriend.
* {{Fetish}}: Due to having the best sex with Judith when she was pregnant with Jake, Alan has a bit of a ''thing'' for pregnant women...
* FoolishSiblingResponsibleSibling: The Responsible to Charlie's Foolish.
* [[FourTemperamentEnsemble Five Temperament Ensemble]]: Melancholic.
* {{Flanderization}}: His cheapness, occasional irresponsibility, and being a leech become his new characterization around Season 9.
* {{Foil}}: To Charlie (and later Walden).
** FoolishSiblingResponsibleSibling: The Responsible to Charlie's Foolish. While not siblings, he and Walden adapt this dynamic starting Season 10, with Alan being the foolish to Walden's responsible (following the latter's CharacterDevelopment and Alan's {{Flanderization}}).
** RedOniBlueOni: The Blue to Charlie's Red.
** SensitiveGuyAndManlyMan: The Sensitive Guy to Charlie's Manly Man.
** SiblingYinYang
* TheFriendNobodyLikes: No one likes him and the show gives plenty of good reasons why they don't.
* HeCleansUpNicely
* HenpeckedHusband: You could not find a better example (although it's more like Henpecked Ex-Husband).
* HilariouslyAbusiveChildhood: Where to begin? He and Charlie had to adapt to living with four different fathers, were dumped at a kibbutz in Israel, and left at summer camp until Thanksgiving, among other things.
* HolierThanThou: He looks down on pretty much everything Charlie does that isn't an age appropriate relationship. Inverted by Season 10, when Alan goes through both AesopAmnesia and even more {{Flanderization}}, and Walden actually has to tell him, "You're better than this."
* HollywoodDateless: He's a very, very, ''very'' strange case. Alan finds himself having sex with a woman every two episodes or so, but his bad luck with maintaining a relationship stems from his crippling insecurity and neediness, MommyIssues, and his tendency to gravitate towards emotionally damaged women.
* HumiliationConga: He cannot catch a break. In any episode where something bad happens to him (which is fairly often), more humiliation is sure to follow.
* InSeriesNickname: "Zippy", from Berta, "The Sponge" from Charlie.
* {{Jerkass}}: Starts to become this in the later seasons, with an overall holier-than-thou attitude, blistering cheapness, and refusal to leave the beach house. He even manages to eclipse Charlie morality-wise in some episodes.
** JerkWithAHeartOfGold: He really does care for his family, despite having to mooch off them, and in Season 12, is dedicated to helping Walden adopt a child.
* KarmaHoudini: Manages to stay in the beach house for 12 years and, judging by the series finale, isn't going anywhere for a long while.
* KavorkaMan: He's managed to hook up with a legion of attractive women, despite being broke, a CosmicPlaything and not particularly good-looking, including mothers Judith and Lyndsey, BrainlessBeauty Kandi, Melissa, and countless others. Nearly all of these have ended in disaster, however.
* LovableSexManiac: Although he's more reserved about it than Charlie.
* MDEnvy: He is a chiropractor that is constantly made fun of for not being a "real doctor."
* MistakenForGay: Sometimes with Charlie, but it turns into a running joke with Walden from Season 9-on. Every woman that learns they live together seems to think they are a couple.
* MamasBabyPapasMaybe: Played with. It's implied that Jake might not even be Alan's son; Charlie can't help but notice how much the exterminator, water deliveryman, and mailman all resemble Jake...
* NoPreggerSex: He claims the best sex he ever had with Judith was during the time she was pregnant with Jake, which explains his offbeat pregnancy fetish.
* NoRespectGuy: If Alan is given any amount of praise whatsoever from his family, it's gone or forgotten by the next episode.
* OddCouple: With Charlie and later with Walden.
* OnlySaneMan: In the early seasons; now he's probably the goofiest character on the show.
* ParentalNeglect: In later seasons, both he and Judith exhibit this towards Jake. In turn, Alan was a victim of this from his own mother.
* TheScrooge: His sponging off of Charlie (and later Walden) was eventually Flanderized into this. He was once ''driven to tears'' from having to pay for a meal.
** Ultimately, his poverty also leads to the demise of his chiropractic business.
* SmugSnake: In Season 11, he flaunts the fact that he is FWB with Lyndsey and best friends with her boyfriend to Walden nonstop.
* TheThingThatWouldNotLeave: You could practically name this trope ''The Alan Harper.'' It's UpToEleven in Season 9 and onwards, plus the series finale implies that he'll get to stay in the beach house for a while.
* TookALevelInDumbass: Goes from being a responsible, competent adult to an immature moron (during the Walden years).
* TookALevelInJerkass: Starting around Season 7, he starts to become increasingly immoral.
* TrueCompanions: With Walden. They bond over having had their lives turned upside down by their divorce and finding a new place to live.
* TheUnfavorite: He's gotten {{flanderized}} into this over time, with recent episodes having Evelyn being repulsed by the very thought of Alan.
* UngratefulBastard: He shows brief glimmers of this throughout the entire series, but it's more obvious in later seasons.
* UnsympatheticComedyProtagonist: Gets [[{{Flanderization}} flanderized]] into this around Season 7-8, although how bad he acts [[DependingOnTheWriter depends on the writer.]] It goes from such despicable acts as cheating on Lyndsey (who actually loves him) with Melissa for meaningless sex and then getting away with it scot-free, to feeling remorse for stealing Judith's diamond earrings to purchase Lyndsey a birthday present. Really, Alan zig-zags between this status in Seasons 7, 8, and 9, but by 10, he's definitely become a {{Jerkass}}.
* VitriolicBestBuds: Played completely straight with Walden.
** He and Charlie were this when the latter was alive and they weren't fighting about something.
* YankTheDogsChain: On numerous unfair occasions, most notably when he found happiness with Kandi and moving into a condo, only for Kandi to leave him a few months later, keep the condo, and have the alimony checks for Alan continue, this time for two ex-wives.

!!! Jacob David "Jake" Harper (Angus T. Jones)
* AbusiveParents: Alan and Judith are this to him.
** Both seemed to at least try to provide a good life for Jake in the early seasons, but after realizing that his life would most likely go nowhere, they stopped caring.
* AdorablyPrecociousChild: Originally.
* BackForTheFinale: He makes a brief appearance in the finale, where he reveals that he left the army and got married.
* BigEater: His defining characteristic, aside from his stupidity.
* BrattyHalfPint: In seasons 2-4. After that he became too old to be considered a "half-pint."
* CatchPhrase: "... Oh yeah!" whenever he's been reminded of something.
* TheChosenOne: Called this by Charlie and Alan. He was the only person who ever [[BreakTheHaughty broke Evelyn]].
* CluelessChickMagnet
* DeadpanSnarker: He has his moments.
* DemotedToExtra: Starting with Season 10, when Jake left to join the military and only appeared sporadically. Even before that, his role slowly started to diminish. By Season 11 he's left the show entirely.
* TheDitz: He becomes more and more dumb every season.
** GeniusDitz: He's an idiot, a {{jerkass}} and is socially inept, but he is a fantastic cook and everyone likes his cooking. He even became a chef when he joined the Army.
* DumbassTeenageSon: Alan and Judith both realized pretty early on that his life was going nowhere.
* FatSlob
* [[FourTemperamentEnsemble Five Temperament Ensemble]]: Phlegmatic.
* FromTheMouthsOfBabes
* {{Gasshole}}: According to Charlie, Jake is flatulent like a whoopee cushion.
* {{Gonk}}: In the later seasons.
* [[HasTwoMommies Has Two Daddies]]: If you can consider Charlie and Alan as this.
* HeCleansUpNicely
* InnocentlyInsensitive: He alternates between being this and being a deliberate JerkAss.
* InsaneTrollLogic: Pretty much his default thought process, especially when he gets older.
* InSeriesNickname: "Buddy" from Alan and "Taterhead" from Charlie.
* {{Jerkass}}: Started in Season 3, got worse as time went on.
* KavorkaMan: In the later seasons. He's [[{{Gonk}} ugly]], [[TheDitz stupid]] and [[JerkAss obnoxious]], yet he manages to pull a threeway with two cute girls ''while in high school'' (and at the age of 16, to be exact).
* LazyBum
* [[LikeFatherLikeSon Like Uncle Like Nephew]]: Jake had quite a bit of success with women just like Charlie did. In high school Jake had a threeway with two girls that he likely lost his virginity to, and slept with his tutor, Zoey's slutty neighbor, Missy (who had a boyfriend), his older girlfriend Tammy, and then Tammy's daughter. Charlie would have been proud.
** If some of Jake's throwaway comments to Alan mean anything, the list might be even longer.
* LiteralMinded: It really annoys people too.
* OddFriendship: With Rose.
* OnlyChildSyndrome: Until Milly came along. He's alright with having a little sister though.
* ParentalNeglect: From both Alan and Judith in later seasons.
* ThePigpen: Combine this with being stupid and an eating machine, and that's Jake in a nutshell.
* PetTheDog: He was genuinely sad for Charlie that he and Chelsea broke up.
* PutOnABus: Starting Season 11. He likely isn't coming back (barring the role being recasted), due to Angus T. Jones having decided to largely give up acting in the wake of becoming a Born-Again Christian, and limiting himself to stage work and occasional independently-produced Christian films.
* TheSlacker
* SomethingWeForgot: In several episodes, Alan temporarily moves out of the house and accidentally leaves Jake behind. Although he doesn't seem to care.
* TheStoner: Becomes a habitual pot smoker in Season 9 (thanks to Eldridge).
* ThoseTwoGuys: With Eldridge.
* TooDumbToLive: How Jake hasn't killed himself in some crazy stunt, we'll never know. The episode where he and Eldridge film ''Jackass''-type antics takes this UpToEleven.
* TookALevelInDumbass / TookALevelInJerkAss: Jake went from a fairly likable and witty but sloppy kid to an ungrateful, obnoxious, braindead pothead.
* UngratefulBastard: What grown-up Jake has become. In his few appearances in Season 10, he seems to be getting better with his attitude towards his father (no doubt a result of enlisting in the Army).

!!! Evelyn Harper (Holland Taylor)
* [[AbusiveParents Abusive Parent]]
* BiTheWay: With Lyndsey's mom, as well as allusions to some experimentation in her younger days.
* DeadpanSnarker: Mostly towards Charlie and Alan.
* DemotedToExtra: She only appeared in one episode in season 10, and four in season 11.
* DirtyOldWoman: She's had sex with women and men both old and young and has no problem engaging in random sex with anyone she finds remotely attractive. According to Alan Harper, she's an "uber-cougar".
* EvilMatriarch: Following a tremendously HilariouslyAbusiveChildhood, Charlie and Alan think so, and from the pieces of it we hear about, they may be right.
* FieryRedhead: When she wants to be.
* [[FourTemperamentEnsemble Five Temperament Ensemble]]: Melancholic.
* GrandeDame
* InSeriesNickname: "Satan" from Charlie. Also called "Death" and "The Black Widow" by Alan once or twice.
* ItsAllAboutMe: AND HOW!
* {{Jerkass}}: Charlie and Alan see her this way, but -
** JerkWithAHeartOfGold: She displays glimmers of being one of these as well. Usually turns out to be related to her narcissism though.
* KarmaHoudini: Except for the occasional scolding, she gets no comeuppance whatsoever for her actions.
* LadyDrunk: She's usually seen with a drink in her hand. True to trope, it's often from a martini glass.
* MoralityPet: She does care about her grandson Jake.
** Although in Season 11, she seems to have forgotten about him in favor of Jenny.
* MrsRobinson: While she is usually seen with guys in her age range, she's been known to do this just as much.
* MyBelovedSmother
* {{Narcissist}}: She is always thinking of herself.
* ParentalFavoritism: While she is by no means a loving mom, and it's barely much, she does seem to prefer Alan for being the more responsible son who settled down and had a kid.
* PetTheDog: She comforted Charlie after Chelsea left him.
* ReallyGetsAround: She's bedded Rose's father, Lyndsey's mother, Walden, Walden's mother, Michael Bolton, Charlie's ex-girlfriend "Bill", Gloria's mother and biological father, and many, ''many'' others.

!!! Jenny Harper (Creator/AmberTamblyn)
* TheAce: When it comes to women.
* TheAlcoholic: To the point where she tries to cure a hangover with vodka.
* ChickMagnet: Seriously. She picks up a girl in a bar that isn't a lesbian without revealing that she herself is a lesbian.
** And already has managed to sleep with non-lesbians, such as Walden's mom Robin, Lyndsey (as part of a threesome with Lyndsey's boyfriend) and Lynda ''freakin''' Carter. Walden even calls it the "lesbian zombie" virus.
* CousinOliver: Introduced in Season 11 to take Jake's place.
* DeadpanSnarker: Inherited Charlie's sarcasm.
* DemotedToExtra: In season 11, she appeared in all episodes except one. In season 12, she only appeared in 3.
* [[FourTemperamentEnsemble Five Temperament Ensemble]]: Leukine.
* GenerationXerox: She is exactly like her father Charlie, to the point of being an {{Expy}}. Berta even says "Charlie's back" when seeing her in action.
* GirlOfTheWeek: Just like dad.
* HardDrinkingPartyGirl: When first introduced, downplayed in later episodes.
* IBangedYourMom: She banged Walden's mom [[UpToEleven in a threesome with Lynda Carter!]]
* InstantSeduction: See ChickMagnet.
* InTheBlood: As much of a womanizer as Charlie was.
* TheLadette: Loves drinking, partying and sex (with women).
* LipstickLesbian: Though her behavior is stereotypically masculine, her appearance is feminine.
* LovableSexManiac: She's a lot nicer than her father was.
* PutOnABus: Moves in with Evelyn in the third episode of Season 12, so that her room can be used for Walden's adopted child.
** TheBusCameBack / BackForTheFinale: Makes an appearance in the last episode, where it turns out she lives in an apartment of her own and has been given a generous $25,000 from Charlie.
* ReallyGetsAround: Are you starting to see the pattern here?
* TheStoner

[[/folder]]

[[folder:Other Main Characters]]

!!! Berta (Conchata Ferrell)
* TheAlcoholic: Implied to be this on multiple occasions, although not to the extent of Charlie.
* AlmightyMom
* AscendedExtra: The character of Berta was so popular with test audiences that she became a member of the main cast.
* BiTheWay: She prefers men, but she's expressed attraction to women over the series and said she's slept with women in the past.
* DeadpanSnarker: Biggest one on the show.
* FieryRedhead
* [[FourTemperamentEnsemble Five Temperament Ensemble]]: Choleric.
* JerkWithAHeartOfGold: She may be snarky and rule the house through fear, but has shown that she cares about her employers in her own way [[MyFriendsAndZoidberg Even]] [[TheFriendNobodyLikes Alan.]]
** And was the first person to accept Alan and Walden's adopted son Louis because [[HiddenDepths she was a foster child herself.]]
* NoLastNameGiven: Even {{lampshaded|Trope}} by Alan in one episode when Walden asks how old he thinks Berta is, and Alan responds with the fact that he "doesn't even know her last name."
* OddFriendship: With Alan, during the rare instances where she's nice to him.
* OnlySaneWoman: She thinks of herself this way and just might be in comparison to everybody else on the show.
* PlatonicLifePartners: With Charlie. WordOfGod is that they're best friends, but neither would admit it.
* PromotionToOpeningTitles: In Season 2.
* ServileSnarker: Up there with the best of them.
* TheStoner: Mentions smoking pot rather frequently in later seasons.
* {{Troll}}: She loves to mess with Charlie and Alan for the fun of it.

!!! Judith Harper-Melnick (Marin Hinkle)
* [[AbusiveParents Abusive Parent]]
* AlphaBitch
* ChildhoodFriendRomance: With Alan.
* DemotedToExtra: Started to become this in Season 9, although now she has officially been PutOnABus.
* EvilMatriarch
* [[FourTemperamentEnsemble Five Temperament Ensemble]]: Choleric.
* {{Hypocrite}}: She scolds Charlie and Alan for numerous things she herself has been known to do.
** And then she left Herb because he cheated on her with his receptionist, even though she has cheated on Herb with men that he considers his friends.
* InvincibleVillain: She's determined to be the biggest bane in Alan's life, and she does it too, [[KarmaHoudini with almost zero backlash]].
* ItAmusedMe: Went from merely bullying Alan for her own needs to just thriving on any moment that will make him squirm.
* ItsAllAboutMe
* {{Jerkass}}: Biggest one on the show.
* KarmaHoudini: Outside getting her ego stung slightly by the odd dry one liner, she has gotten away with taking Alan for everything (though that was also Charlie's fault), as well as constantly hurling abuse at him, trying to control his life and being a full on {{Jerkass}} to him for almost a decade as well as treating Herb and Jake like crap and indirectly interfering with Charlie's life as a result. It only seems to be set in stone now she has been PutOnTheBus.
* MamasBabyPapasMaybe: The paternity of her daughter Milly is called into question before the girl was even born (as Milly was conceived around the time Judith and Herb were separated whereupon she and Alan had a brief affair). Moreover, ''everyone'' (except Herb) can see that Milly resembles Alan a great deal, causing Judith a great amount of aggravation. [[TheUnreveal The question itself is never actually answered]], but it really does look like Alan is the biological father.
* PutOnABus: As of Season 10.
** TheBusCameBack: In a single episode, where Walden and Alan tried to convince her to take back Herb.
** BackForTheFinale: Made a cameo in the series finale, where she reveals to Alan that Jake gave her a fair amount of his winnings from Vegas. Alan himself wound up being the only character to get nothing (from neither Jake nor a recently-revealed-to-be-alive Charlie), which essentially closes the deal on Judith's KarmaHoudini status before she hangs up on Alan for good.
* SuddenlySexuality: Although she just used this as an excuse to divorce Alan.
** WhatCouldHaveBeen: It was intended to be genuine at first, but after finding out ''{{Friends}}'' [[ItsBeenDone used a similar plot]], they rewrote it as a lie, helping establish her manipulative Jerkass persona.
* TakingTheKids: Used this as a threat from time to time on Alan. [[spoiler: She actually followed through by taking Milly away when she divorced Herb.]]
* TookALevelInJerkass: She was always a {{Jerkass}}, but mostly just in [[ItsAllAboutMe a self centered manner]]. As time passed she became actively vindictive, mooching off Alan and [[ItAmusedMe making his life a living hell at every opportunity]]. Her callousness became indiscriminate too, neglecting and abusing Jake, and treating Herb as badly as she had Alan.

!!! Rose (Melanie Lynskey)
* AxCrazy: God help anyone that tries to stand in her way.
** Charlie ended up in this situation, too. [[spoiler:Turns out she really didn't kill him, but actually intended to, and would have if a goat hadn't intervened.]]
* BigScrewedUpFamily: Her father is just as crazy as her and starts stalking Evelyn after dating briefly. According to her grandmother, this happens when one marries [[KissingCousins a first cousin]].
* BitchInSheepsClothing: More prevalent in later seasons, where she flat-out admits being a stalker and doing crazy things to the Harpers just for the hell of it.
* [[HandsomeLech Beautiful Lech]]
* TheChessmaster: When Charlie starts thinking that Rose was making him sick on purpose, Alan points out that he obviously caught the flu from an unrelated incident...Yep, turns out that it was Rose who arranged for him to meet this woman who gave him the flu. Similarly, if you start thinking that [[WhoWouldBeStupidEnough no one]] would stage a wedding to a [[InventedIndividual nonexistent groom]] in order to make someone jealous, or any other idea that underestimates her in such a way, the plot will prove you wrong.
* {{Cloudcuckoolander}}
* ComedicSociopathy: She has yet to be prosecuted for stalking and murdering Charlie, despite basically confessing the latter to the assembled crowd at his funeral.
* DemotedToExtra: With Charlie dead, it's very unlikely that Rose will ever play a major role in the series again, although it has been shown that she is now stalking Walden.
* {{Flanderization}} / TookALevelInJerkass: She originally gave off a sweet and innocent vibe to conceal her true nature, but in later seasons, becomes a full-on AxCrazy bitch who takes delight in doing nasty things to get her way, and has no problem letting anyone know.
** Killing Charlie definitely cemented this status.
* FlowerMotifs: Her clothes embroidered with flower patterns, topped with her name.
* [[FourTemperamentEnsemble Five Temperament Ensemble]]: Sanguine.
* IncestIsRelative: Her grandparents are first cousins.
* {{Jerkass}}: In her own way, although she may not seem like it at first glance. And she did murder Charlie [[spoiler: She actually faked his death and held him captive in her basement]]. But, to be fair, he did cheat on her and as Berta states, "Never cross a crazy woman." She also stalked Walden and had her ferrets attack Walden when he dumped her.
* KarmaHoudini: All of the stalking Charlie over the years and then killing Charlie. [[spoiler: Then it turns out she faked his death and then kidnapped him and locked him in her basement for several years without remorse.]] And she got away with everything.
* LoveMakesYouCrazy
* MsFanservice
* OddFriendship: With Jake.
* OfficialCouple: With Charlie, at first.
* PutOnABus
** TheBusCameBack: In the introductory episode of Season 9 and three episodes of Season 10 (this time stalking Walden).
* StalkerWithACrush: A self-proclaimed "Stalker with a Crush", too, towards Charlie (and later Walden).
* SugaryMalice
* {{Yandere}}

!!! Kandi (April Bowlby)
* BackForTheFinale: Makes a cameo in the series finale, when Alan (thinking he is going to be murdered by a brainwashed Charlie) tells that although they were only together for a short while, he still loves her.
* BiTheWay: Charlie points out that Kandi has probably slept with more women than Alan. Alan finds this a [[GirlOnGirlIsHot very fun thought indeed]].
** And then there was that little encounter with Lyndsey that both agreed never to tell Alan about.
* TheBrainlessBeauty
* TheDitz
* [[FourTemperamentEnsemble Five Temperament Ensemble]]: Sanguine.
* HiddenDepths: She does occasionally show some intelligent moments, and seems to be a decent piano player.
** She's a decent enough actor and can accurately say forensic stuff without mispronouncing it.
* InnocentlyInsensitive
* LiteralMinded
* MsFanservice
* TookALevelInJerkass: Before she left Alan, she was much nicer to him than everyone else.
* YouLookFamiliar: Bowlby played a minor character two episodes before being introduced as Kandi. Though referred to - jokingly - as "Bubbles" by Alan, she is credited as "Kimber", this could be counted as an EarlyBirdCameo.

!!! Chelsea (Jennifer Bini Taylor)
* BackForTheFinale: Made a cameo in the series finale, where she got a generous check from Charlie, as well as an apology for breaking her heart.
* [[FourTemperamentEnsemble Five Temperament Ensemble]]: Phlegmatic.
* {{Hypocrite}}: She storms out on Charlie because he slept with her best friend Gail when she was in Mexico with Brad, the guy she left Charlie for to begin with. She then ends their relationship for good because he slept with her again despite storming out on him.
* MoralityPet: She was one for Charlie and brought out his heart of gold and encouraged his good qualities.
* MsFanservice: She was often seen in a nightgown that showed off her cleavage.
* NiceGirl: Before [[TookALevelInJerkass taking a level in Jerkass]], she treated Alan (and to an extent, Charlie) the nicest out of everybody on the show.
* TookALevelInJerkass: She dumped Charlie for Alan's lawyer Brad. She then left him all over again once he sleeps with her friend Gail while they were separated and Chelsea turns into a complete bitch who happily dances (metaphorically) on Charlie's grave despite the good times they had.
* YouLookFamiliar: Taylor had already guest starred in previous episodes, including the pilot.

!!! Walden Schmidt (Creator/AshtonKutcher)
* AlwaysSomeoneBetter: To Alan.
* BungledSuicide: He tried to drown himself in the ocean outside of the beach house after his wife left him, but apparently didn't realize the water would be so cold.
* ButtMonkey: He's still much better off than Alan, but has started to verge into this territory recently.
* CharacterizationMarchesOn: Around the time when Walden's beard was gone, so was his childlike personality. Alan originally had the upper hand as his "guidance" following his divorce, but by Season 10, Walden is clearly the more mature one in the house, often acting as Alan's conscience to show how far his personality has gone.
* ChickMagnet: Seriously. Every girl on the show who has met him expressed attraction towards him in some way.
* DeadpanSnarker: Especially to Alan.
* DitzyGenius: Started off in this zone, got better but still has the occasional moment.
* EvenTheGuysWantHim: Alan didn't mind kissing him, the therapist questioned her orientation after his hug.
* {{Flanderization}}: In Season 11, he starts to develop some shades of neediness, unable to sleep with a woman without declaring his love for her.
* [[FourTemperamentEnsemble Five Temperament Ensemble]]: Sanguine.
* IBangedYourMom: He had sex with Evelyn, despite Alan's warnings that she was a cougar.
* ManChild / OneOfTheKids: Originally, but his personality has greatly matured over the past two seasons, and at this point it's clear who is the more mature one in the beach house.
* MistakenForGay: It used to be a running gag, but now it's been upped to OncePerEpisode.
* MrFanservice
* NiceGuy: A decent guy, save for being a little sharp-tongued to Alan (though it's not entirely unwarranted).
* NoNudityTaboo: In his introduction episode.
* OneHourWorkWeek: He is the head of a billion dollar company, yet seems to have tons of free time to hang out with Alan, and is hardly ever shown working.
* OnlySaneMan / ReasonableAuthorityFigure: He is starting to become something like this in the beach house, in comparison to Alan, Jenny, and Berta.
* ParentingTheHusband: This situation is what led Bridget away.
* TheStoner: Even has a drawer containing pot hidden inside his nightstand.
* TrueCompanions: With Alan.
* VitriolicBestBuds: In Season 9, he was fairly sympathetic and generous to Alan, but in Season 10, he seems to have discovered most of Alan's gnomish qualities and threatens to kick him out of the house multiple times. Regardless, he and Alan know that whatever happens, they can count on each other.

[[/folder]]

[[folder:Recurring Characters]]
!!!Herb Melnick (Ryan Stiles)
* DeadpanSnarker: You'd have to be after living with Judith.
* GentleGiant: He's 6'4", and is easily nicer than the rest of the cast.
* HenpeckedHusband: Like Alan before him. The poor guy gets treated like crap by his wife.
* LoveMartyr: Seriously. Herb has the patience to rival Buddha for being able to put with Judith.
* MamasBabyPapasMaybe: Look above with Judith.
* NiceGuy: The nicest guy on the show.
* OddFriendship: With Alan.
* [[spoiler: YourCheatingHeart: Cheated on a receptionist at his work, driving Judith to divorce him.]]

!!! Courtney Leopold[=/=]Sylvia Fishman (Jenny [=McCarthy=])
* GoldDigger: She uses rich men for money and sex without remorse.
* {{Jerkass}}: She's a con artist and scammed Charlie into buying a Ferrari and then scammed him personally out of fifty thousand dollars before getting arrested and then showed up at his house to use him for sex and money and then starts using Walden for sex and money until Walden's ex-wife bribes her to leave him alone.
** JerkassHasAPoint[=/=]NotSoDifferent: She comments to Alan that he has no place calling her out on being a gold digger using Walden when he's using Walden for his money too and she's kind of right. The only difference is that Courtney's having sex with him and Alan isn't.
* KarmaHoudini: She got away with scamming Charlie and Walden for money without remorse.
* ManipulativeBitch: She's very good at it, given how successful she is at being a GoldDigger. She successfully manipulated Charlie into bed and blackmailed him into buying a Ferrari or have their sexual liason exposed to Evelyn and Teddy.

!!! Dr. Linda Freeman (Jane Lynch)
* DeadpanSnarker: Inbetween giving helpful advice that Charlie rarely ever listened to and once assured Charlie the sarcasm is a flat rate.
* EveryoneHasStandards: She was horrified when she heard Charlie's plan to have a therapist so he could cop an insanity plea just incase he snapped and killed Alan.
** She was incredibly shocked and kind of disgusted when she heard Charlie's idea of being truly intimate with a woman is not using a condom.
* OnlySaneMan: Despite the sarcasm, she's a smart and competent therapist who gives really helpful advice that would benefit Charlie's life if he actually listened to her.

!!! Gordon (J.D. Walsh)
* ButtMonkey: Offscreen, his life may be just as bad as Alan's: He was only a substitute for Charlie when he was dating Rose, and mentioned in an episode that he got a decent job as well as a wife within a 2-year radius, only for all of that to leave him. He's also envious of Charlie's lifestyle and easygoing demeanor, calling him a "genius."
* ChuckCunninghamSyndrome: Disappeared after Season 8.

!!! Russell (Martin Mull)
* {{Catchphrase}}: "What are you, a cop?" whenever someone questions something he's doing morality wise.
* CloudCuckooLander: He can go off on some really bizarre tangents; justified since he's a hard drug user.
* TheStoner: Misuses all of the pharmaceuticals in his midst to outrageous extremes.

!!! Lyndsey [=MacElroy=] (Courtney Thorne-Smith)
* TheAlcoholic: Naturally, like Charlie, her drinking habits have been toned up over time. In season 12, she goes to rehab and quits drinking entirely.
* CompressedVice: Portrayed as an out-of-control alcoholic in ""Not in My Mouth!", with no previous indications of a drinking problem. Her alcohol issues appeared inconsequentially in the following episodes. Eventually, she was flanderized into a raging alcoholic, before going sober in season 12.
* DerailingLoveInterests: In season 11, when Alan starts dating Larry's sister, Gretchen who is just like him, Lyndsey is turned into a pathetic drunk who's obsessed with Alan, though earlier she was just barely tolerating him. In season 12, after Gretchen leaves Alan, Lyndsey reverts to her former self.
* {{Flanderization}}: Goes from being a genuinely kindred spirit into a bitchy alcoholic.
* {{Gasshole}}: One reason that she likes Alan is because she can fart with him around, and he won't leave her, because he won't be able to find anyone better.
* IWasYoungAndNeededTheMoney: Her explanation for appearing in a porn movie.
* JustFriends: With Charlie, despite what Alan thought.
* MsFanservice
* RelationshipRevolvingDoor: Dated Alan consistently in season 8 until she left him for her ex-husband, then they got together again briefly and broke up due to Alan's paranoia that she was sleeping with Charlie. They got back together in Season 9 because she can fart like crazy and he won't leave her. They were engaged in Season 10 and then they broke up, seemingly for good. However, in the second episode of Season 11 she began sleeping with Alan again, but they are not in a relationship, as she has a boyfriend, Larry. Alan eventually wanted to restart their relationship and planned on proposing to her, but Larry did it before he could. After that, Lyndsey stopped sleeping with Alan. Later, she tried to restart the affair, but by then, Alan was dating Larry's sister, so he rejected Lyndsey. In season 12, when Alan is single again, they make yet another attempt to renew their relationship, which results in Alan proposing to her, and Lyndsey enthusiastically saying yes after seeing the ring. The series finale shows her attempting to find out its value (and presumably) pawn it, leaving the question open-ended as to whether she and Alan stayed together or not.
* SingleWomanSeeksGoodMan: To Alan.
* TookALevelInJerkass: At first she was perfectly nice to Alan and seemed to genuinely love him. Then he accidentally burnt her house down.
* YourCheatingHeart: In Season 11 she's involved in a committed relationship to a NiceGuy... and cheats on him with Alan because he's really terrible at sex.

!!! Eldridge [=MacElroy=] (Graham Patrick Martin)
* ChuckCunninghamSyndrome: Never seen or mentioned after the Season 9 finale.
* TheDitz / DumbBlonde: He's [[UpToEleven even dumber then Jake is]].
* DumbassTeenageSon: For Lyndsey.
* {{Jerkass}}: Is incredibly disrespectful to his mother and Alan.
* LiteralMinded: Perhaps even more so than Jake.
* PutOnABus: He joined to the military along with Jake at the season 9 finale, and hasn't been seen since.
* SatelliteCharacter: His only defining character traits are being Lyndsey's son and Jake's friend.
* ThoseTwoGuys: With Jake.
* TheStoner: Combine this with being an idiot and that's his character in a nutshell.
* ToxicFriendInfluence: He's definitely rubbed off on Jake.

!!! Larry (D.B. Sweeney)
* BerserkButton: He was content with Alan having dated Lyndsey, but when Walden accidentally brought up that Alan was sleeping with Lyndsey while she was dating him...
* CrazyJealousGuy: To the point where he hires a private investigator (who turns out to be Rose) to get the scoop on the guy Lyndsey's been cheating on him with (unaware that it's his new best friend, "Jeff"). He thinks it's Walden, though.
* TheDitz: He was completely oblivious to many of the slip-ups Alan made about sleeping with Lyndsey.
* EasilyForgiven: Returns in Season 12 as a close friend of both Alan and Walden, so apparently he did eventually forgive Alan.
* {{Flanderization}}: And in less than ten episodes, too. He started off as being simply too naïve to pick up on the fact that Alan and Lyndsey were cheating behind his back; then, he's suddenly a full-fledged Ditz who isn't bright in the least.
* GoodPeopleHaveGoodSex: Subverted. He's incredibly bad at it, which is why Lyndsey is sleeping with Alan.
* MySisterIsOffLimits: Inverted: He's delighted to find out that Alan has been sleeping with his sister.
* NiceGuy: Treated Alan the nicest out of everybody on the show, despite only being around for a few episodes.

[[/folder]]