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Harper Family

    Charles Francis "Charlie" Harper 
https://static.tvtropes.org/pmwiki/pub/images/charlie_harper_6.jpg
Played by: Charlie Sheen

  • The Ace: At least compared to Alan. Women and money just fall into his hands!
  • Adam Westing: Charlie Harper is basically Charlie Sheen without the "Sheen". It started to feel more uncomfortably similar to the real Charlie Sheen's decreasing sanity until his firing.
  • The Alcoholic: 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.
  • Always Someone Better: To Alan.
  • And There Was Much Rejoicing: Next to no one had a single nice thing to say about him during his funeral (Alan tried).
  • Anything That Moves:
    (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?
  • Ashes to Crashes: 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. In the series finale it turned out that Charlie was actually still alive and the ashes belong to a goat called Billy.
  • Asshole Victim: The women who attend his funeral certainly think so. Whether or not he was is up for interpretation, though there is much to validate that he certainly was.
  • At Least I Admit It: Whatever flaws Charlie has, he doesn't deny who he is. Not that it makes him a more endearing person, since he has admitted on more than one occasion that if there is a Hell he's going there when he dies for all he's done.
  • Back for the Dead: In the series finale.
  • Bastard Boyfriend: To Chelsea. When she was suffering back pain due to large breasts he tried to prevent her from having breast reduction surgery so that she'll stay attractive to him.
  • Benevolent Boss: Most of the time to Berta, he paid her well and at the wake after his funeral, Berta says he was the best boss she ever had.
  • Big Bad: In the series finale.
  • Big Brother Bully: To Alan, in their childhood.
  • Broken Ace: 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.
  • Bunny-Ears Lawyer: 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.
  • The Bus Came Back: The character, not the actor, returned in the series finale for all of about 10 seconds.
  • Bus Crash: Charlie technically 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. Then it became subverted in the series finale, where it was revealed he was in fact still alive... then subverted again when he was killed by a falling piano in its last ten or so seconds.
  • The Casanova: Sleeps with a woman every other episode, if not more.
  • Casual Kink: According to one of the women at Charlie's funeral, he liked being spanked while wearing her panties.
  • Character Development: 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. Unfortunately it was thrown out the window in later seasons.
  • Chick Magnet
    Alan: They just drop out of the sky for him!
  • Cool Uncle: To Jake, at least originally. Maybe subverted in the series finale, where he sends Jake a check for $25,000.
  • Deadpan Snarker: One of the biggest, if not the biggest, on the show.
  • Death by Sex: Rose catches him showering with another woman during their vacation to Paris and pushes him in front of a train. However, this was subverted in the finale: Rose actually kept him locked up in her basement for four years.
  • Depraved Kids' Show Host: "Is There A Mrs. Waffles?"
  • Disappeared Dad: He decided that he didn't want to be in his daughter Jenny's life anymore and just sent child support.
  • Dreadful Musician: 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.
  • Dropped a Bridge on Him: A train, more specifically. In the finale, a piano... sort of.
  • Dude, Where's My Respect?: 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.
  • Everyone Has Standards:
    • 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 attractive underage granddaughter's advances (though it's mostly because he doesn't want to go to prison for it).
  • Foolish Sibling, Responsible Sibling: The Foolish to Alan's Responsible.
  • Five-Temperament Ensemble: Choleric.
  • Flanderization: As the seasons progress, Charlie becomes an even heavier drinker and an even bigger Jerkass. He was also stated to have been hard drug user after his death, though this may have been part of a large Take That! aimed at Charlie Sheen.
  • The Ghost: He becomes this after his "death", where he is constantly mentioned by the other characters, especially Alan, despite not appearing in person.
  • Girl of the Week: One has to wonder at times how Charlie Harper is the less-exaggerated version of the actual Charlie Sheen.
  • Handsome Lech: 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.
  • Hilariously Abusive Childhood: 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!"
  • Instant Seduction: Mia was the only one this didn't work on.
  • It Amused Me: His reason for picking on Alan so much.
  • It's All About Me: He's so self-obsessed that when Alan was suicidally depressed all he was thinking about was how Alan's outburst embarrassed him.
  • Jerk with a Heart of Gold: A selfish, egotistical, and narcissistic womanizer, but he does have a good side to him, such as when he gives up his engagement and happy future just to make sure his family has a place to stay.
  • Jerk with a Heart of Jerk: 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.
  • Just Friends: With Lyndsey, despite what Alan thought.
  • Karma Houdini Warranty: Charlie's jerkassery never seemed to catch up to him until he was McLeaned at the beginning of Season 9.
  • Kid-anova: Was a Casanova in his youth as well.
  • Killed Off for Real: Between Seasons 8 and 9, (presumably) by Rose. Subverted in the series finale where it's revealed he was alive this whole time, before he legitimately gets killed off by a Piano Drop.
  • Lack of Empathy: Whenever people around him suffer he will often 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 take advantage of people's emotional and social problems for his own benefit.
  • Ladykiller in Love: With Mia, Chelsea, and Rose. They were the only women he ever proposed to, but never married any of them.
  • Laser-Guided Karma: The girls who attend the funeral seem to view his "death" as this.
  • Lovable Sex Maniac: Subverted. It caused a lot of resentment from Alan and Evelyn. Jake was cool with it though.
  • Manchild: According to Alan - "You are a child! A high maintenance child!" He's also been called a "professional boy-toy" and a perpetual adolescent living a dissolute lifestyle to the point his own therapist says he suffers from Peter Pan syndrome.
  • Mommy Issues: Even more so than Alan.
  • Narcissist: Charlie is always thinking of himself and has a massive ego. When others around him suffer he finds it amusing but then expects them to sympathize with him whenever he suffers.
  • The Nicknamer: Mostly to Alan, Jake and Evelyn. Alan was "The Sponge", Jake was "Numbnuts", "Tater head" and "Pumpkin head" and Evelyn was "Satan".
  • Noodle Incident: Most of Charlie's sexual escapades, especially the ones before Alan and Jake move in.
  • Not So Different: 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 Oedipus Complex.
  • Not Staying for Breakfast: Charlie's specialty. A lot of the time, he doesn't even know the girl's name.
  • Odd Couple: With Alan, of a familial variety. Alan's a neurotic, luckless, Straw Loser, whereas Charlie's a filthy rich casanova who coasts through life without a care in the world. Having Alan living with him seriously cramps Charlie's lifestyle, but also gives him some much-needed grounding where he'd otherwise probably drink or screw himself to death.
  • One-Hour Work Week: 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.
  • Parental Neglect: Scorns Evelyn for this particular reason.
  • Platonic Life-Partners: With Berta. Word of God is that they're best friends, but neither would admit it.
  • The Pornomancer: His talent of instantaneously bedding women borders on the supernatural.
  • Put on a Bus to Hell: 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). Until the series finale retconned this by revealing he wasn't actually dead. As to how Alan and Jake managed to see him it can be chalked up to Alan being on medication at the time and Jake having just smoked weed in the hospital bathroom.
  • Really Gets Around: For most of the show, he has a new girl in his bed almost Once per Episode.
  • Red Oni, Blue Oni: The Red to Alan's Blue.
  • Rogue Protagonist: After being one of the three central characters for the first 8 seasons, he returns in the Grand Finale out to kill his brother Alan and his replacement Walden for continuing on without him as if he never existed.
  • Sensitive Guy and Manly Man: The Manly Man to Alan's Sensitive Guy.
  • Sex God: He's portrayed as being a great lover, probably thanks to all the practice.
  • Smug Snake: Mostly towards Alan, whenever he's bragging about his latest conquest.
  • Stylistic Suck: His jingles.
  • Took a Level in Jerkass: Goes from caring about Alan and Jake in his own way to screwing with them just for the hell of it.
  • Unproblematic Prostitution: Has an entire contact list full of hookers on his phone.
  • Unsympathetic Comedy Protagonist: Most of the time.
  • Unwitting Instigator of Doom: He himself says he's like "a malevolent force of nature," in that he causes a lot of problems for people, but not intentionally.
    • Both Jake and Alan have said that whenever Charlie sleeps with someone even remotely connected to their lives, they pay the price.
      • Alan lost everything in his divorce after Charlie seduced his attorney and then dumped her moments before Alan needed her.
      • Jake's teacher Miss Pasternak snapped after Charlie dumped her.
      • Speaking of which, she returned in a later episode and revealed that Charlie's dumping of her did not end well for her; She had a nervous breakdown and was fired and blackballed from teaching. Then she lost her house and was disowned by her parents. Now she lives in a cheap motel and works as a stripper
  • Vitriolic Best Buds: When he wasn't fighting with Alan or Evelyn, they were this.
  • What Did I Do Last Night?: This is a weekly ritual for him.
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    Alan Jerome Harper 
https://static.tvtropes.org/pmwiki/pub/images/alan_harper.JPG
Played by: Jon Cryer

  • Abhorrent Admirer: He attracts old women, like Judy's or Melissa's mother.
  • Abusive Parents: To Jake, starting with Season 6. He was (or at least tried to be) a decent parent in the earlier seasons, but between Charlie's hedonistic lifestyle, Judith's abuse and Jake himself becoming an ever more irresponsible idiot, Alan became increasingly jaded and just gave up (there is a sad degree of Truth in Television to this).
  • Adorkable: Specially in earlier seasons. While still "mourning" over his divorce, he often gets excited if something interesting happens.
  • Aesop Amnesia:
    • After Walden's leading a double life to meet a woman blew up in his face, 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.
  • Because You Were Nice to Me: He falls in love with Charlie's older, motherly girlfriend for this reason.
  • Bitch in Sheep's Clothing: 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, 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 Nice Guy.
  • Born Unlucky: Despite all his faults, one cannot deny that Alan was born with some kind of curse hanging over his head.
  • Butt-Monkey: Alan is an effeminate, hapless and dorky loser who's constantly neurotic, awkward and insecure and most people don't respect him for it. 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.
  • Camp Straight: Charlie once described him as his girlfriend's "gay friend."
  • The Cassandra: He repeatedly warns Walden about Rose, and is eventually proven right.
  • Childhood Friend Romance: With Judith. Ends terribly.
  • Cosmic Plaything: Just about everything is out to get him, and is merciless in execution.
  • Covert Pervert: Although he tries to act more controlled than Charlie when it comes to women, Alan is perhaps even more of a pervert. Completely loses the "covert" part in later seasons, openly masturbating in the living room and announcing he is going to watch porn when he finds Louis is out of the house.
  • The Dandy: Primps about his clothing fairly often.
  • A Date with Rosie Palms: 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). Up to Eleven in later seasons.
  • Deadpan Snarker: He generally has a quippy retort ready for whenever Charlie's antics annoy him or get out of hand, or when he's talking to Judith when Jake isn't around.
  • Extreme Doormat: Has consistent bad judgement, and had to pay alimony to Judith until she got remarried.
  • Failure Is the Only Option: 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...
  • Flanderization: Formerly just broke, unlucky and geekish yet still trying to retain his dignity and moral compass (and raise his son right), Alan gradually becomes a spineless and shameless freeloader who will do anything for money/free stuff and has no intention of moving out of his brother's (later Walden's) house. His poverty and cheapness are constant joke fodder. His general clumsiness, bad luck, social ineptitude, poor judgment, and Camp Straight tendencies are also gradually dialed up. He does get less neurotically uptight and more adventurous in later seasons, as the implied result of giving in to his inner Jerkass - whereupon he also becomes, or reveals he's always been, almost as much of a shallow horndog as Charlie.
  • Foil: To Charlie (and later Walden).
  • Foolish Sibling, Responsible Sibling: The Responsible to Charlie's Foolish. While not siblings, he and Walden adopt this dynamic starting Season 10, with Alan being the foolish to Walden's responsible (following Walden's Character Development and Alan's Flanderization).
  • Five-Temperament Ensemble: Melancholic.
  • The Friend Nobody Likes: Due to Alan being a penny pinching hypocritical cheapskate who mooches off his brother and occasionally mother, no one really likes or respects him, they just tolerate him. Jake especially is disgusted and has little respect for Alan.
  • Henpecked Husband: You could not find a better example (although it's more like Henpecked Ex-Husband).
  • Hilariously Abusive Childhood: 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. Also having to deal with Charlie being a shitty brother who bullied him relentlessly growing up.
  • Holier Than Thou: He looks down on everything Charlie does that isn't an age appropriate relationship. Inverted by Season 10, when Alan goes through both Aesop Amnesia and even more Flanderization, and Walden actually has to tell him, "You're better than this."
  • Hollywood Dateless: He's a very, very, very strange case. Alan has had his own fair share of hooking up with some very attractive women (though nowhere near Charlie's level), but he has bad luck with maintaining a relationship which stems from his crippling insecurity and neediness, Mommy Issues, and his tendency to gravitate towards emotionally damaged women.
  • Humiliation Conga: He cannot catch a break. In any episode where something bad happens to him (which is fairly often), more humiliation is sure to follow.
  • In-Series Nickname: "Zippy", from Berta, "The Sponge" from Charlie.
  • Jerk with a Heart of Gold: Despite being a penny pinching hypocritical cheapskate who mooches off his more successful family members and Walden, he really does care for his family and tries to be a supportive brother to Charlie and a responsible father to Jake. In Season 12, he is dedicated to helping Walden adopt a child and once the child arrives, he quickly forms a bond with him.
  • Kavorka Man: He's managed to hook up with a legion of attractive women, despite being broke, a Cosmic Plaything and not particularly good-looking, including mothers Judith and Lyndsey, Brainless Beauty Kandi, Melissa, and countless others. Nearly all of these have ended in disaster, however.
  • Lovable Sex Maniac: Although he's more reserved about it than Charlie. Averted in the later seasons.
  • Mama's Baby, Papa's Maybe: 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...
  • MD Envy: He is a chiropractor that is constantly made fun of for not being a "real doctor" by pretty much everyone.
  • Mistaken for Gay: 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.
  • No Pregger Sex: Inverted. 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.
  • No Respect Guy: If Alan is given any amount of praise whatsoever from his family, it's usually undone by the end of the episode.
  • Not So Different: 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, has cheated on women several times and done some other morally questionable stuff throughout the series.
  • Odd Couple: With Charlie and later with Walden.
  • Only Sane Man: In the early seasons; by the end he's hands down the most bizarre and dysfunctional character on the show.
  • Papa Wolf: He tells off Evelyn for crushing Jake's self-esteem when he aces a test and calls out Charlie a couple times for treating Jake poorly.
  • Parental Neglect: In later seasons, both he and Judith exhibit this towards Jake. In turn, Alan was a victim of this from his own mother. Truth in Television sadly.
  • Red Oni, Blue Oni: The Blue to Charlie's Red. He is, however, the Red to Walden's Blue.
  • The Scrooge: 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.
  • Sensitive Guy and Manly Man: The Sensitive Guy to Charlie's Manly Man.
  • Smug Snake: In Season 11, he flaunts the fact that he is FWB with Lyndsey and best friends with her boyfriend to Walden nonstop.
  • Stopped Caring: As time goes on he sheds his Holier Than Thou attitude and embraces his freeloading ways, openly and proudly declaring himself to be scum.
  • The Thing That Would Not Leave: You could practically name this trope The Alan Harper. It's Up to Eleven in Season 9 and onwards.
    • It's worth noting that in the pilot, Alan insists he's only moving in for "a couple of days", but by Season 10, he happily tells Walden to his face that he's gonna die in the beach house.
  • Took a Level in Dumbass: Goes from being a responsible but socially awkward adult and the voice of reason to an immature, socially stunted goofball who is totally incapable of taking care of himself.
  • Took a Level in Jerkass: Goes from a flawed but generally Nice Guy to a Bitch in Sheep's Clothing to a full on Jerkass with only the occasional Pet the Dog moment.
  • True Companions: With Walden. They bond over having had their lives turned upside down by their divorce and finding a new place to live.
  • The Unfavorite: He's gotten flanderized into this over time. When Charlie was around, Evelyn always insisted that Alan was the "good son", but after Charlie's "death", she insists he was the one she was most proud of and is openly repulsed by the very mention of Alan.
  • Ungrateful Bastard: He shows brief glimmers of this throughout the entire series, but it's more obvious in later seasons.
  • Unsympathetic Comedy Protagonist: Eventually becomes no better than Charlie himself.
  • Vitriolic Best Buds: Played straight with Walden. He and Charlie were this when they weren't fighting about something.
  • Yank the Dog's Chain: 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 
https://static.tvtropes.org/pmwiki/pub/images/jake_harper.jpg
Played by: Angus T Jones

  • Abusive Parents: 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.
  • Adorably Precocious Child: Originally.
  • Back for the Finale: He makes a brief appearance in the finale, where he reveals that he left the army and got married.
  • Big Eater: His defining characteristic, aside from his stupidity.
  • Bratty Half-Pint: In seasons 2-4. After that he became too old to be considered a "half-pint."
  • Broken Pedestal: As the series goes on, he becomes more aware of Charlie and Alan's flaws and he distances himself from them a few times when they cost him several relationships or embarasss him in front of girls.
  • Catchphrase: "... Oh yeah!" whenever he's been reminded of something.
  • The Chosen One: Called this by Charlie and Alan. He was the only person who ever broke Evelyn.
  • Clueless Chick Magnet: Throughout the series, Jake has had alot of attention from girls even before he started really dating. Eventually he drops the Clueless part in the later seasons.
  • Deadpan Snarker: He has his moments before Flanderization kicked in, mostly at Charlie and Alan's expense.
  • Demoted to Extra: 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.
  • The Ditz: He becomes more and more dumb every season.
  • Dumbass Teenage Son: Alan and Judith both realized pretty early on that his life was going nowhere.
  • Five-Temperament Ensemble: Phlegmatic.
  • From the Mouths of Babes: Especially in later seasons, when Charlie's influence is starting to get to him. Alan is understandably not happy that his pre-teen son occasionally talks like an aged bachelor.
  • Gasshole: According to Charlie, Jake is flatulent like a whoopee cushion.
  • Generation Xerox: Jake had quite a bit of success with women just like Charlie did. Jake had sex with a plethora of women once he got older, including a threeway with two girls, his tutor Megan (who briefly became his girlfriend), Jennifer - Zoey's slutty neighbor (and a grown woman at that), Missy (who had a boyfriend), his older girlfriend Tammy, and then Tammy's daughter. Charlie would have been proud.
  • Genius Ditz: 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.
  • Gonk: In the later seasons.
  • Has Two Mommies: If you can consider Charlie and Alan as a gender-inversion.
  • Hidden Depths: He's a fantastic chef, and after Charlie died he mentions to Alan that he was well aware how lonely and miserable Charlie really was deep down.
  • Innocently Insensitive: He alternates between being this and being a deliberate Jerkass.
  • Insane Troll Logic: His default thought process, especially when he gets older.
  • In-Series Nickname: "Buddy" from Alan and "Taterhead" from Charlie.
  • Jerk with a Heart of Gold: He becomes more jerky starting Season 3 and got worse as time went on. Despite that, it's clear he still loves his father and is overall still a well-meaning kid, even if he is a bit of a dumbass.
  • Kavorka Man: In the later seasons. He's ugly, stupid and obnoxious, yet he manages to pull a threeway with two cute girls while in high school.
  • Kids Raiding the Wine Cabinet: After he entered his "stupid teenager" phase would do this periodically with his Uncle Charlie. Charlie tended to be more angered at the missing liquor than the drunken antics that followed.
  • Lazy Bum: Anything that doesn't involve eating or messing around is too much effort for him. His poor performance in school is at least at much to blame on his dirt-poor work ethic as it is his stupidity.
  • Likes Older Women: In season 9, he was 17 but had sex with a 24 year-old woman, after lying about his age. In season 10, he went out with a 36 year-old who had three kids, one of which was older than him. By that point, he was of age.
  • Literal-Minded: 80% of jokes involving Jake will revolve around him taking something way too literally, much to the irritation of everyone else.
  • Morality Pet: To Evelyn, who does have some measure of care towards him, and in Season 6 even offers to pay for his college and a car.
  • Odd Friendship: With Rose, up until season 9 when she made it clearly obvious that she killed his Uncle Charlie. He too became afraid of her but to a lesser extent than Alan.
  • Only Child Syndrome: Until Milly came along. He's alright with having a little sister though.
  • Out of Focus: From Season 10 onwards, he was Demoted to Extra, before leaving the show altogether in Season 11.
  • Parental Neglect: From both Alan and Judith in later seasons.
  • The Pigpen: Combine this with being stupid and an eating machine, and that's Jake in a nutshell.
  • Pet the Dog: He was genuinely sad for Charlie that he and Chelsea broke up.
  • Put on a Bus: Starting Season 11, he left the show for good (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. He did however return for a cameo in the finale.
  • The Slacker: Lazy and underachieving.
  • Something We Forgot: In several episodes, Alan temporarily moves out of the house and accidentally leaves Jake behind. Although he doesn't seem to care.
  • The Stoner: Becomes a habitual pot smoker in Season 9, thanks to Eldridge's influence.
  • Supreme Chef: Is revealed to be very good at cooking.
  • Those Two Guys: With Eldridge, his partner in stupidity.
  • Too Dumb to Live: 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 Up to Eleven.
  • Took a Level in Dumbass: Jake went from a fairly witty but sloppy kid to a braindead pothead.
  • Took a Level in Jerkass: He also becomes more ungrateful and obnoxious towards Charlie and Alan.
  • Took a Level in Kindness: In Season 10, his attitude toward his father improves exponentially.

    Evelyn Harper 
https://static.tvtropes.org/pmwiki/pub/images/evelyn_harper.jpg
Played by: Holland Taylor

  • Abusive Parents: Was this to her sons, being a selfish and negligent excuse of a mom who screwed them up in many different ways.
  • Deadpan Snarker: Mostly towards Charlie and Alan.
  • Demoted to Extra: She only appeared in one episode in season 10, and four in season 11.
  • Dirty Old Woman: She's slept with men and women both young and old and has no problem engaging in random sex with anyone she finds remotely attractive. According to Alan, she's an "uber-cougar".
  • Evil Matriarch: Following a tremendously Hilariously Abusive Childhood, Charlie and Alan think so, and from the pieces of it we hear about, they may be right.
  • Fiery Redhead: When she wants to be.
  • Four-Temperament Ensemble: Melancholic.
  • The Friend Nobody Likes: No one genuinely likes Evelyn or wants to associate with her, not even her sons or grandchildren. Charlie even mentions that if she hadn't sold him the house, she wouldn't know where he lives.
  • Going Commando: On the night that was supposed to be the first date of her and Russell, after the latter ruins the moment by bringing a lady friend, she mentions going upstairs to put on panties.
  • Grande Dame: What she's going for, what with the high-class mannerisms and the pretensions of culture, but she's ultimately a little too sleazy to pull it off.
  • In-Series Nickname: "Satan" from Charlie. Also called "Death" and "The Black Widow" by Alan once or twice.
  • It's All About Me: She's literally incapable of thinking of anyone but herself. Even when it seems like she's being uncharacteristically generous, it's because she has an ulterior motive.
  • Jerkass: Charlie and Alan see her this way, but -
  • Jerk with a Heart of Gold: She displays glimmers of being one of these as well. Usually turns out to be related to her narcissism though.
  • Karma Houdini: Except for the occasional scolding, she gets no comeuppance whatsoever for her actions.
  • Lady Drunk: She's usually seen with a drink in her hand. True to trope, it's often from a martini glass.
  • Mrs. Robinson: On occasion.
  • My Beloved Smother: Played with. She was outright neglectful when Alan and Charlie were growing up and remains emotionally unavailable as they grow up. She still tries to insist herself into their lives as much as possible, mainly to satisfy her own misconception of herself a concerned, unappreciated mother. And even she does that, she's only concerned with her own desires.
  • Narcissist: She is always thinking of herself.
  • Parental Favoritism: 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.
  • Pet the Dog: She comforted Charlie after Chelsea left him and has sometimes displayed genuine affection for Jake.
  • Really Gets Around: 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 
https://static.tvtropes.org/pmwiki/pub/images/jenny_harper.jpg
Played by: Amber Tamblyn

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Other Main Characters

     Berta 
https://static.tvtropes.org/pmwiki/pub/images/berta.jpg
Played by: Conchata Ferrell

  • The Alcoholic: Implied to be this on multiple occasions, although not to the extent of Charlie.
  • Ascended Extra: The character of Berta was so popular with test audiences that she became a member of the main cast.
  • Deadpan Snarker: Biggest one on the show.
  • Fiery Redhead: Usually pretty laid-back but get her riled-up enough and she'll slip into this.
  • Five-Temperament Ensemble: Choleric.
  • Jerk with a Heart of Gold: She may be snarky and rule the house through fear, but has shown that she cares about her employers in her own way Even Alan. And was the first person to accept Alan and Walden's adopted son Louis because she was a foster child herself.
  • Odd Friendship: With Alan, during the rare instances where she's nice to him.
  • Only Sane Woman: She thinks of herself this way and just might be in comparison to everybody else on the show.
  • Only One Name: Even lampshaded 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."
  • Platonic Life-Partners: With Charlie. Word of God is that they're best friends, but neither would admit it.
  • Promotion to Opening Titles: In Season 2.
  • Really Gets Around: Berta implied she's had her share of affairs in life, even mentioning she once had sex with a guy for a tank of gas.
  • Servile Snarker: Up there with the best of them. She even mentions that Charlie would have to pay her to not be one.
  • The Stoner: Mentions smoking pot rather frequently in later seasons.
  • Troll: She loves to mess with Charlie and Alan for the fun of it.
  • Wisdom from the Gutter: Berta is often the one taking care of problems and pointing out personal issues in the Harper Household, despite being implied to live in a heavily lower class household with a considerably dysfunctional and morally loose family.

     Judith Harper-Melnick 
https://static.tvtropes.org/pmwiki/pub/images/judith_harper_melnick.JPG
Played by: Marin Hinkle

  • Abusive Parents: Her lack of regard for Jake crosses into emotional abuse on more than one occasion. Which is more or less an extension of how she treats everyone else.
  • Back for the Finale: 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 Karma Houdini status before she hangs up on Alan for good.
  • The Bus Came Back: In a single episode, where Walden and Alan tried to convince her to take back Herb.
  • Childhood Friend Romance: With Alan.
  • Demoted to Extra: Started to become this in Season 9, although now she has officially been Put on a Bus.
  • Evil Matriarch: She's not a great mother, being exasperated with Jake and having even less faith in him than Alan.
  • Five-Temperament Ensemble: Choleric.
  • Hate Sink: Arguably the most obnoxious of the main cast, and lacks the Hidden Heart of Gold that makes the others tolerable.
  • 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.
  • Invincible Villain: She's determined to be the biggest bane in Alan's life, and she does it too, with almost zero backlash.
  • It Amused Me: Went from merely bullying Alan for her own needs to just thriving on any moment that will make him squirm.
  • It's All About Me: To call her self-absorbed would almost be too kind.
  • Jerkass: The biggest in the show. Even though she had already kicked Alan out of their house and gotten the right to an extremely high alimony, which had given Alan no choice but to live with his brother Charlie, she loved to destroy his life even further and extort even more money from him. She also seemed to have no love for her son Jake, and still had the nerve to complain at Alan's parenting skills. And it became obvious that she treated her new husband, Herb, just as badly as she had treated Alan. And except for one episode, where she actually allowed Alan to live with her and Herb after he had a fight with Charlie (which was very out of character for her), she had no redeeming qualities whatsoever. She actually started out as a reasonably realistic person in the face of a divorce and and confusion about her own sexuality, but gradually became more narcissistic and selfish as the show went on.
  • Karma Houdini: 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 Put On The Bus.
  • Mama's Baby, Papa's Maybe: 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. The question itself is never actually answered, but it really does look like Alan is the biological father.
  • Put on a Bus: As of Season 10.
  • Suddenly Sexuality: Although she just used this as an excuse to divorce Alan. It was intended to be genuine at first, but after finding out Friends used a similar plot, they rewrote it as a lie, helping establish her manipulative Jerkass persona.
  • Taking the Kids: Used this as a threat from time to time on Alan. She actually followed through by taking Milly away when she divorced Herb.
  • Took a Level in Jerkass: She was always a Jerkass, but mostly just in a self-centered manner. As time passed she became actively vindictive, mooching off Alan and 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 
https://static.tvtropes.org/pmwiki/pub/images/rose.JPG
Played by: Melanie Lynskey

  • Ax-Crazy: God help anyone that tries to stand in her way. Charlie ended up in this situation, too. Turns out she really didn't kill him, but actually intended to, and would have if a goat hadn't intervened.
  • Big, Screwed-Up Family: Her father is just as crazy as her and starts stalking Evelyn after dating briefly. According to her grandmother, this happens when one marries a first cousin.
  • Bitch in Sheep's Clothing: More prevalent in later seasons, where she flat-out admits being an obsessive and creepy stalker and doing crazy things to the Harpers just for the hell of it.
  • The Bus Came Back: She makes a few guest appearances in the post-Charlie seasons.
  • The Chessmaster: 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 no one would stage a wedding to a 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: She definitely dwells on her own planet. Don't mistake strangeness for stupidity, though.
  • Demoted to Extra: Starting Season 9, her appearances become extremely sporadic, though it makes sense as she's no longer a part of the main cast and her love interest, Charlie, is "dead".
  • Faux Affably Evil: After Flanderization.
  • Flanderization: She originally gave off a sweet and innocent vibe to conceal her true nature, but in later seasons, becomes a full-on Ax-Crazy bitch who takes delight in doing nasty things to get her way, and has no problem letting anyone know.
  • Flower Motifs: Her clothes embroidered with flower patterns, topped with her name.
  • Five-Temperament Ensemble: Sanguine.
  • Jerkass: In her own Faux Affably Evil way.
  • Karma Houdini: She stalked Charlie for years, attempted to kill him, and then kidnapped and locked him in her basement for several years without remorse. In the series finale, she walks away with zero repercussions for her actions.
  • Kissing Cousins: Her grandparents are first cousins.
  • Love Makes You Crazy: Become insanely obsessed with Charlie after a one-night-stand with him.
  • Ms. Fanservice: She's an attractive woman who has been in some form-fitting outfits.
  • Odd Friendship: With Jake.
  • Put on a Bus: After Charlie's "death".
  • Stalker with a Crush: Towards Charlie and later Walden.
  • Sugary Malice: She speaks sweetly, but the contents she says is often disturbing.
  • Throw the Dog a Bone: Establishing that she and Charlie did get married before his death probably was the closest the show could go to giving Rose a happy ending. Of course, her faking his death and locking him in her basement does put a damper on this in hindsight.
  • Took a Level in Jerkass: Killing Charlie definitely cemented this status. In the series finale it's revealed she didn't actually kill him, but the intention was still there, and she did keep him prisoner in a basement for four years.
  • Yandere: During Charlie's funeral, is plain everyone believes she killed him, she instead kept him locked in her basement for years.
  • Your Cheating Heart: Her interest in Walden becomes this once it's revealed she faked Charlie's death and kept him prisoner in her basement. The finale even makes clear she continued her "wifely" duties with Charlie during this period. Ironically, Charlie's wandering eye is what drove her to this in the first place.

     Kandi 
https://static.tvtropes.org/pmwiki/pub/images/kandi.jpg
Played by: April Bowlby

  • Back for the Finale: 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.
  • Brainless Beauty: She's very dimwitted and is loved mostly by her looks.
  • The Ditz: Show best when Alan hires her as his assistant. She can't even use the phone properly.
  • Five-Temperament Ensemble: Sanguine.
  • Hidden Depths:
    • She does occasionally show some intelligent moments, and seems to be a decent piano player.
    • She's a decent enough actress and can accurately say forensic stuff without mispronouncing it.
  • Innocently Insensitive: Extremely blunt and inappropriate at times, simply because she's too much of a ditz to know what's appropriate and when.
  • Literal-Minded: She can actually get what someone's saying most of the time, but you have to spell it out exactly the way you mean it. Figurative language is completely lost on her;
  • The Missus and the Ex: Bonds with both of Alan's main Love Interests, Judith and Lyndsey.
  • Ms. Fanservice: Wears many Sexy Whatever Outfits when not being a Walking Swimsuit Scene.
  • Took a Level in Jerkass: Before she left Alan, she was much nicer to him than everyone else.
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     Chelsea Melini 
https://static.tvtropes.org/pmwiki/pub/images/chelsea_melini.jpg
Played by: Jennifer Taylor

  • Amazingly Embarrassing Parents: Her mother is a racist, homophobe white supremacist and Her dad Tom, who is a Navy veteran, seemed to be the same but it is later revealed in Season 7 that he has been in love with his old Navy buddy for many years.
  • Anorgasmia: In "Captain Terry's Spray-On Hair", Charlie's horrified when he finds out that he's been unable to bring her to orgasm for a while and she confesses that she was irrationally distraught over her ex-husband marrying another woman, meaning he's "over her", and it began affecting her sex life. After she works it out with Charlie, she's having The Immodest Orgasm the next time they get to bed.
  • Back for the Finale: Made a cameo in the series finale, where she got a generous check from Charlie, as well as an apology for breaking her heart.
  • 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 Gail again despite storming out on him.
  • I Can Change My Beloved: Tried her best to turn Charlie into a better person.
  • The Immodest Orgasm: Charlie says she yells out "Gaaaa" when the sex is really satisfying. She's trying to say "God" but it comes out as "Gaaaa".
  • Kindhearted Cat Lover: She's very kind and has a cat as a pet named "Sir Lancelot".
  • Morality Pet: She was one for Charlie and brought out his heart of gold and encouraged his good qualities.
  • Ms. Fanservice: She was often seen in a nightgown that showed off her cleavage.
  • Nice Girl: Before taking a level in Jerkass, she treated Alan (and to an extent, Charlie) the nicest out of everybody on the show.
  • Relationship Revolving Door: Was to the point of leaving Charlie many times during their relationship, but they always patched up at the end. Until he slept with her Best Friend.
  • Took a Level in Jerkass: 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.

     Walden Schmidt 
https://static.tvtropes.org/pmwiki/pub/images/walden_schimdt.jpg
Played by: Ashton Kutcher

  • Always Someone Better: To Alan.
  • Bigger Is Better in Bed: Alan mentions he's "Hung like an elephant" when Walden strips naked in front of him. Berta, Judith and Jenny are all very impressed upon seeing him naked.
  • Bungled Suicide: 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.
  • Butt-Monkey: He's still much better off than Alan, but has started to verge into this territory recently.
  • Characterization Marches On: 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.
  • Chick Magnet: Seriously. Every girl on the show who has met him expressed attraction towards him in some way.
  • Deadpan Snarker: You'd have to be to put up with Alan.
  • Ditzy Genius: Started off in this zone, got better but still has the occasional moment.
  • Even the Guys Want Him: 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.
  • Five-Temperament Ensemble: Sanguine.
  • I Banged Your Mom: He had sex with Evelyn, despite Alan's warnings that she was a cougar.
  • Manchild: Originally, but his personality greatly matured during his time on the show.
  • Mistaken for Gay: It used to be a running gag, but was later upped to Once per Episode.
  • Mr. Fanservice: Unlike Charlie who's almost a Kavorka Man, Walden is much more attractive and gets plenty of Fanservice scenes of his own.
  • Nice Guy: Started off as an innocent, childlike decent guy. This started to disappear after he got his haircut and his personality began to change, though he's still nicer than most of the rest of the cast.
  • One-Hour Work Week: He is the head of a billion dollar company, yet seems to have tons of free time to hang out with the Harpers and is hardly ever shown working. Of course, this could be entirely because he's the head a billion dollar company, meaning he's free to leave the day-to-day work to his employees, which is very much Truth in Television.
  • Only Sane Man: He is starting to become something like this in the beach house, in comparison to Alan, Jenny, and Berta.
  • Parenting the Husband: This situation is what led Bridget away.
  • Red Oni, Blue Oni: The Blue to Alan's Red.
  • Shameless Fanservice Guy: In his introduction episode, shows no shame when he gives a Naked First Impression to Berta and Judith. Neither of them mind.
  • Suicide by Sea: Attempted at the start of season 9, only to turn into a Bungled Suicide.
  • Suspiciously Similar Substitute: He is Charlie's official replacement, being the filthy-rich Chick Magnet who Alan lives with for free.
  • The Stoner: Even has a drawer containing pot hidden inside his nightstand.
  • Took a Level in Jerkass: Walden went from a childlike Nice Guy to this after he had his haircut. Once that happens, he appeared to show less respect for Alan.
  • True Companions: With Alan.
  • Vitriolic Best Buds: In Season 9, he was sympathetic and generous to Alan, but by Season 10, he has discovered most of Alan's gnomish qualities and threatens to kick him out of the house multiple times. Regardless, he never does as he and Alan know that whatever happens, they can count on each other.

Recurring Characters

    Herb Melnick 
Played by: Ryan Stiles

  • Chuck Cunningham Syndrome: Despite being a popular character, Herb doesn’t make an appearance in the series finale. Nor is there any mention of him. It’s unfortunate seeing how it managed to cram every single main character over the course of twelve seasons into the episode, surely the writers could’ve found a way to include him.
  • Deadpan Snarker: You'd have to be after living with Judith.
  • Gentle Giant: He's 6'6", and is easily nicer than the rest of the cast.
  • Henpecked Husband: Like Alan before him. The poor guy gets treated like crap by his wife.
  • Love Martyr: Seriously. Herb has the patience to rival Buddha for being able to put with Judith.
  • Mama's Baby, Papa's Maybe: Look above with Judith.
  • Nice Guy: The nicest and most normal guy on the show.
  • Odd Friendship: With Alan, though it's more due to the situation (Herb is the husband of Alan's ex-wife). Personality-wise, they're actually pretty similar. Maybe Judith Has a Type...
  • Stalker with a Crush: Towards Lyndsey. He finally gets to sleep with her in the last season.
  • Your Cheating Heart: Cheated on a receptionist at his work, driving Judith to divorce him.

     Courtney Leopold/Sylvia Fishman 
Played by: Jenny McCarthy

  • Gold Digger: 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.
  • Jerkass Has a Point: 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.
  • Karma Houdini: She got away with scamming Charlie and Walden for money without remorse.
  • Manipulative Bitch: She's very good at it, given how successful she is at being a Gold Digger. She successfully manipulated Charlie into bed and blackmailed him into buying a Ferrari or have their sexual liaison exposed to Evelyn and Teddy.

     Dr. Linda Freeman 
Played by: Jane Lynch

  • Deadpan Snarker: In between giving helpful advice that Charlie rarely ever listened to and once assured Charlie the sarcasm is a flat rate.
  • Everyone Has Standards:
    • She was horrified when she heard Charlie's plan to have a therapist so he could cop an insanity plea just in case 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.
  • Only Sane Man: 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 
Played by: JD Walsh

  • Butt-Monkey: 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."
  • Chuck Cunningham Syndrome: Disappeared after Season 8.

     Russell 
Played by: 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.
  • The Stoner: Misuses all of the pharmaceuticals in his midst to outrageous extremes.

     Lyndsey MacElroy 

  • The Alcoholic: Naturally, like Charlie, her drinking habits have been toned up over time. In season 12, she goes to rehab and quits drinking entirely.
  • Compressed Vice: Portrayed as an out-of-control alcoholic in "Not in My Mouth!", with no previous indications of a drinking problem. Her alcohol issues appeared inconsistently in the following episodes. Eventually, she was flanderized into a raging alcoholic, before going sober in season 12.
  • Dark Secret: Her past job as a one-time porn actress was treated like this by Alan.
  • Derailing Love Interests: 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.
  • Gold Digger: While not nearly as bad as all the other women in the series, in the series finale she went to a pawm shop to see how much her engagement ring from Alan was worth! Though it is probably unlikely she actually pawned it.
  • I Was Young and Needed the Money: Her explanation for appearing in a porn movie.
  • Jerk with a Heart of Gold: She had her bitch moments, but for the most part is usually sweet and understanding towards those she cares about.
  • Just Friends: With Charlie, despite what Alan thought.
  • Ms. Fanservice: In Universe, Herb finds her merely being his neighbor very distracting.
  • Relationship Revolving Door: 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.
  • Single Woman Seeks Good Man: To Alan.
  • Took a Level in Jerkass: At first she was perfectly nice to Alan and seemed to genuinely love him. Then he accidentally burnt her house down and her behavior just became worse and worse. Granted, he burned her house down.
  • Your Cheating Heart: In Season 11 she's involved in a committed relationship to a Nice Guy... and cheats on him with Alan because he's really terrible at sex.

     Eldridge MacElroy 

     Larry 
Played by: DB Sweeney

  • Beware the Nice Ones: 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...
  • Crazy Jealous Guy: 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.
  • The Ditz: He's not bright.
  • Easily Forgiven: Returns in Season 12 as a close friend of both Alan and Walden, so he apparently did forgive Alan.
  • Flanderization: He starts off as being 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.
  • Good People Have Good Sex: Subverted. He's incredibly bad at it, which is why Lyndsey is sleeping with Alan.
  • My Sister Is Off-Limits!: Inverted: He's delighted to find out that Alan has been sleeping with his sister.
  • Nice Guy: Treated Alan the nicest out of everybody on the show, despite only being around for a few episodes.
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