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Season 1

  • Charlie telling Jake that if he wanted to lie about writing a song, it'd be Stairway to Heaven, not a jingle for Maple Loops cereal.
  • How Charlie disciplines Jake for letting seagulls in his house. He buys him an XBOX and a bunch of different games and then doesn't let him play it for a month.
  • At the very end of the episode with Megan Fox:
    Judith: So how was your weekend?
    Jake: Uncle Charlie says I don't have to tell you.
  • In episode 3, when Alan mentions visiting Disneyland:
    Charlie: Alan, I'm not thrilled about having one small rodent in my house. (Jake's guinea pig) Why would I drive fifty miles to see their kingdom?
  • In the episode "My Doctor Has A Cow Puppet", Charlie imitating Judith to role Alan up during his therapy session.
    Charlie (as Judith): Is this gonna take much longer? 'Cause I have to get to a massage and a tennis lesson that he's paying for.
    Alan: Tennis? Since when do you play tennis?
    Charlie: I told you, but you never listen. (to Dr. Friedman) He never listens, thank God is brother took him in.
    Alan: Okay, I am warning you...
    Charlie: You're warning me?
    • And in the same therapy session, Jake's child psychiatrist Dr. Linda Freeman decides to give Charlie a piece of her mind after seeing him immaturely mock Alan for being "whipped".
    Charlie Meow! Fitchoo!
    Alan Okay, I am really getting tired of that!
    Dr. Linda Freeman Okay you know what, Charlie? I don't really care for that much either. If you like, we can schedule you another session to deal with your fear of vaginas.
    • And at the end of the episode, when Charlie and Alan leave the child psychiatrist office and a little girl sitting in the waiting area with her mother sees them.
    Little Girl (to her mother) How long am I going to have to keep coming here?

Season 2

  • Episode 4, Alan teaching Jake how to use the electric car was very amusing.
    Alan: Now, you know, this is the brake and this is the gas.
    Jake: I thought it was electric.
    Charlie: He's got you there, Alan.
    Alan: Okay... this is the brake and this the... electric.
    • It gets even funnier when Jake actually starts driving the thing.
      Alan: Now, just give it a little tap.
      Jake: Is it on?
      Alan: No.
      (Jake presses on the pedal and the car suddenly speeds up)
      All: WHOOOOOOOAAAA!!
      Charlie & Alan: BRAKE! BRAKE! BRAKE!
  • Episode 7, Judith accuses Alan of speaking derogatory things to Jake about her.
    Judith: Alan, have you been badmouthing me?
    Alan: B-B-Badmouthing you? To whom?
    Judith: To Jake.
    Alan: Oh, to Jake. No, why?
    Judith: His attitude towards me lately is so disrespectful. I have to wonder where he's getting it from.
    Alan: Well I can assure you that I always make it a point to speak highly of you in front of our son.
    Judith: What about your brother?
    Alan: Oh, with Charlie I'm completely honest.
    Judith: That's not what I meant.
    Alan: I know. Smug grin
    Charlie walks into the scene, holding a bottle of beer.
    Charlie: Hey Judith.
    Judith: Charlie, have you said derogatory things about me to Jake?
    Charlie: No why, did you want me to?
    Judith: I don't why he's acting this way, avoiding me, ignoring me, acting like I'm the enemy.
    Charlie: But you get why I'm doing it, right?
  • Episode 10: The episode begins with Charlie writing the opening theme for an animated adaptation of Oshikuru Demon Samurai and Jake listening to the "rough version" - said version is a bouncy and upbeat song which Jake dislikes because the source material is dark in nature and the song doesn't capture that, as a result of Charlie spending minimal effort learning about said material (i.e. he did not learn it at all). Later on he works with Jake to produce a much better version and, finally, the show comes up on TV. The theme song that plays is... the first version. The reason? The network preferred it over the newer versions.
    Jake: That's not what we wrote! That's your original sucky version!
    Charlie: What can I tell you? The network liked that one better.
    Jake: What are they, brain damaged?
    Charlie: Welcome to show-business, kid.
  • Episode 13: Judith stays at Charlie's due to an earthquake in LA that hit her house hard. Alan ends up staying there briefly due to jealousy and then Charlie and Alan make a plan to get her out by making Judith jealous. When Judith meets Alan's date, Charlie plays certain notes on the piano in response to what's said. When Judith leaves, he plays Na Na Hey Hey Kiss Him Goodbye's chorus.
  • SQUAB!
    • Made even better when the voices that usually chorus "mennnn" during the scene changes say "squab" instead.
  • Episode 14: Alan pretends to not be home when Judith arrives, followed by Charlie's answering Judith's questions with commentary from the Animal Planet. When Judith leaves after bitching about Evelyn, Charlie says "I'll tell Alan you stopped by." just to piss her off a bit more.
    • Alan is trying to get Jake to study for his history test, Charlie walks in drunk and ends up unintentionally helping Jake study for it by making it a pop quiz.
      • Not to mention Charlie asking Alan to drive him to the local 7 Eleven so he can get some snowballs and an eskimo pie.
  • In Episode 16, Alan and Charlie sit down at their kitchen table to relax and share a cold one.
    Alan: Oh, that's good. I just keep having this nagging feeling that I've forgotten something.
    Charlie: Hey, if you forgot it then it probably wasn't all that important.
    Alan: Yeah, I guess.
    Hard cut to Jake standing outside a soccer field in the rain, looking wet, miserable and very, very pissed off.
    • This gag about Parental Neglect is given an even more savage callback later, when Charlie chides Alan for missing Jake's school play, only to realize he never actually brought Jake home with him.
      Alan: I should tell him I'm sorry I wasn't there.
      Charlie: Yeah, you should.
      Alan: Is he in his room?
      Charlie: (his expression slowly shifts in horror) ....Uh, oh.
      Hard cut to Jake standing in the rain again outside of his school, using his kite prop for his Ben Franklin costume to try to stay dry, until lightning crashes in the sky and he decides that he's better off ditching the kite.
  • Season 2 finale, after Judith's done her typical threat of legal consequences because of Jake's behavior for giving her a $25 chip from Caesar's Palace that he won from Charlie, Charlie and Alan mock Judith in high pitched tones that just sells the scene.

Season 3

  • Episode 2, Alan needs Charlie to be his receptionist for the day so he can stop Jake getting expelled from school. Charlie with a lot of caffeine in his system when they're in the car tapping a song and making suggestions for how to make money in traffic jams is hilarious.
  • Episode 5, Alan calls Charlie a misogynist, you think he'd respond with some witty response, instead he grabs a dictionary.
  • One of Alan's finest would be him naming off movies in a movie trivia game but adding "Blow it out your ass!" during a meltdown of his in "That Special Tug".
    • And later Alan says they should go see Jake, who's at a sleepover, because Alan has a feeling Jake needs him:
      Charlie: Is that like some sort of telepathy thing?
      Alan: Exactly.
      Charlie: I see.
      Beat. Charlie slaps Alan upside the head.
      Alan: Ow!
      Charlie: Did you know I was gonna do that?
      Alan: No!
      Charlie: Then I wouldn't trust your psychic powers.
    • Really, the entire episode. Did you forget "There's not enough bowel movements left!"?
  • Charlie's showing Alan how their mother can make any good thing bad and is later proven right.
    Alan: Hey, mom, here's some good news: it seems, with medical breakthroughs, the average life span will soon be 100 years.
    Evelyn: Wonderful, more time to be ignored by your children.
  • Alan states that "I need to communicate after lovemaking. I need to share!" after a chat with his girlfriend Kandi proves to be rather...silly.
    Charlie: Well maybe you should've thought of that before you started boinking a girl with the IQ of Tickle Me Elmo.
  • After Jake mentions about going to his first boy-girl party, Alan and Charlie get into discussion about who should give him advice, where Charlie delivers this quote to his hopeless romantic brother:
    Charlie: Face it, Alan. What can you bring to the table other than a lifetime of abject failure with women?
    Alan: It's not a lifetime yet!

Season 4

  • The entire opening scene in "Don't Worry, Speed Racer," but especially:
    Alan: Look, Jake, it, it, it— it's not that you have to be particularly smart to have sex.
    Berta and Charlie: Yeah, look at your dad!
    • And then there's this:
      Charlie: You wanna know what kind of pie your Uncle Charlie likes? (Alan interrupts him) Oh, come on. (Alan interrupts him again)
      Berta: I'm guessing cherry- (Alan interrupts her with an annoyed expression)
    • Not to mention...
      Charlie: Okay, honestly, how much more damage could we have caused?
  • Charlie offers to take Alan out for dinner and Alan protests about not getting a choice in where they go like Charlie's dates and Charlie decides to troll him by acting like Alan's his date and making lots of innuendo to make Alan shut up.
  • Alan at least tries to pretend to be happy for Judith when he learns that she is getting remarried. As soon as Judith leaves, though...
    Charlie: Five, six, seven, eight...
    Alan: (Conga-ing) No more a-li-mo-ny! No more a-li-mo-ny! No more a-li-mo-ny!
  • Episode 15, Rose is helping Jake study, he needs to learn three contributions to society that the Romans made, Berta asks Charlie the same question.
    Charlie: Orgies, wine and bulimia. Go ahead, ask me about the Greeks.
  • In an episode when Alan and Charlie go out clubbing and Alan is whining about the noise:
    Charlie: Will you listen to yourself?!
    Alan: I CAN'T listen to myself. All I hear is aaaaaaaaaaaaaaaaaaaaaaaaaa!! (walks to the piano) C-Sharp! C-Sharp is the sound of approaching deafness!! aaaaaaaaaaaaaaaaaaaaaaaaaaaaaa!!
  • Charlie's passed out at the table and Jake sees him there, when Berta walks in, she makes the following comment.
    Berta: You really shouldn't see him like this, Jake. (whips out a towel and places it over Charlie's face) There! Now you can enjoy your breakfast.
    • And moments later, when he wakes up with the towel still in place...
      Charlie: Oh my God, I'm blind! (Alan removes the towel) It's a miracle!
  • Why Charlie wants to go to Evelyn's funeral.
    Alan: You'll be going to Mom's funeral, won't you?
    Charlie: Of course! As the eldest son it's my obligation to pound in the stake.
    Alan: Typical. Nothing for Alan to do.
    Charlie: OK, you can cut off her head and hold it up for the villagers.
  • From the episode "I Merely Slept With A Commie", Charlie's Brutal Honesty and Alan's completely deadpan reaction to how they're supposed to convince Evelyn to change her ways so people will actually want to come to her funeral.
    Charlie: What are we gonna say, Alan? "Hey Mom, you're a crazy she-bat and the only way people will mourn at your funeral is if your delighted sons turn it into a three day beer-bash with go-go dancers!"
    [Beat]
    Alan: Well, we wouldn't start there.
    • From the same episode a few minutes before, when Charlie tries to get out of the house rather than listen to Evelyn's self-obsessed ranting.
      Alan: There are alternatives to running away from her.
      Charlie: Yeah, but we'd get caught and you'd sell me out for a reduced sentence.
  • This bit of dialogue between Charlie, Evelyn and Charlie's latest girlfriend, Lydia:
    Evelyn: So Charlie, how long have you been seeing this...lovely woman?
    Charlie: Er, how long has it been, sweetie?
    Lydia: Are you telling me you don't remember when we met?
    Evelyn: The way he drinks?! There's a good chance he doesn't remember coming down the stairs!
    Lydia: Did his father drink?
    Charlie: What choice did he have?
  • Myra explaining why Judith doesn't like her.
    Myra: Maybe it's my hair, maybe it's my job, maybe it's my hobbies or maybe it's because I offered my brother a thousand dollars not to marry her.
    Charlie: I know what you mean. I did the same to my brother.
    Myra: Really?
    Charlie: Well, actually it was a thousand dollar hooker.
  • Mixed with a Moment of Awesome, Alan's phone cojones.
    Alan: (to Judith on the phone) I'll tell him [Charlie] to keep his hands off Myra. And then, I'll tell the rain not to fall, the earth not to spin, and you to STOP NAGGING ME! [hangs up] Oh, boy, I'm gonna pay for that.
    Berta: You know what your problem is? Phone cojones.
    Alan: Excuse me?
    Berta: When you're on the phone with her, you got boulders between your legs. The minute you hang up, you're as smooth as a Ken doll.
  • Charlie whilst he's drunk off his ass at the start of Episode 22, mostly the inability to unlock the front door.
    Charlie: Oh hey Alan, come on in!
    Alan: Why don't you come in?
    Charlie: I can't... I lost my key.
    • In the morning, Berta walks into the kitchen and sees Jake eating a bowl of chilli. Berta immediately knows what that means.
      Berta: Oh no... Charlie's blackout chilli.
      Jake: It's delicious!
      Berta: No argument here.
    • Jake is confused as to why it's called "blackout chilli" until:
      Charlie: (Walks in) Geez, Jake, how many times have I told you not to crap up my kitchen!?
      Jake: But I'm not the one who... Oooooh.
    • Alan trying to get Charlie to help Jake with his book report.
      Charlie: Relax, I'll take Jake to the DMV to get his license.
      Alan: Book report!
      Charlie: (Holding up a can of beans) Beaaans!

Season 5

  • Charlie's balls are on fire due to some stuff he used to get the grey out of his pubic hair.
    Indian doctor: We have a saying in my country. "You can put a tuxedo on a goat, but it's still a goat."
    Charlie: Yeah, well, we have a saying in my country, too: "Help me, my balls are on fire!"
  • Jake sneaks out to go to a concert and sneaks back in with a drugged up Charlie. They get caught by Alan.
    Alan: [to Jake] Do you have any idea how much trouble you're in?
    Charlie: I do not. Do you have any idea how beautiful you look in that light?
    Alan: I'm not talking to you.
    Charlie: Yeah, well, I'm not talking to you either, except for right now, this is me talking to you, but, no longer. [makes pop sound]
    Alan: Would you please just... go to sleep?
    Charlie: Okey-dokey. [grabs pillow and goes out of view]
    Alan: [to Jake] You and I have some talking to do.
    Charlie: Will you make up your freaking mind?
  • Charlie has to give a concert as Charlie Waffles, he finds the solution to his stage fright.
    Charlie: Hey, Alan, I figured out what went wrong in seventh grade!
    Alan: What?
    Charlie: I hadn't started drinking yet! [walks in drunk]
    Alan: Charlie, you have to get out there.
    Charlie: Right, the little bastards await.
    • And during the concert, no one seems to care that he's drunk. Not even his manager.
      Alan: Doesn't it bother you that he's loaded?
      Manager: (Shrugs) He's a musician; it'd bothered me if he wasn't.
  • Alan summarizing the majority of the series when Charlie sleeps with someone that's connected to someone important in his life.
    Charlie: How could you take the fall for me?
    Alan: I don't know, but it always seem works out that when you get laid, I get screwed!
  • Charlie and Herb's discussions about bushes, planting seeds in soil and making sure the soil is moist

Season 6

  • Charlie's cooking in episode 3, particularly the cinnamon buns tube.
    Charlie: I christen thee H.M.S Kitchen Table, godspeed.
    Charlie hits the tube on the kitchen table three times and it doesn't open.
    Charlie: I think we have a bad bun tube.
    Alan: Here, give me that.
    Alan hits it on a kitchen bench and opens it.
    Alan: Just gotta know how to whack it.
    Charlie: I bow to your superior expertise.
  • Charlie tries to help out Miss Pasternak get back on her feet after what happened the last time they met. It ends the exact same way.
  • It's horrible on Charlie and Alan's part, but their threatening Jake with military school is just hilarious. (He's not going to military school.)
  • Episode 8, Charlie catches Jake licking his piano after getting grounded for mooning some girls.
    Charlie: What are you doing?
    Jake: Playing 'Smoke on the Water'
    Charlie: With your tongue?
    Jake: Pretty cool, huh?
    Charlie: That's not cool, it's disgusting. Alan, get in here! [Alan comes in] Your kid's licking my piano!
    Alan: Jake, don't lick your uncle's piano.
    Jake: But I'm bored.
    Alan: Go read a book.
    Jake: I don't wanna read a book.
    Charlie: Then go lick a book! [Jake leaves] How long is this whole grounding thing gonna go on for?
    Alan: Two weeks.
    Charlie: Two weeks?
    Alan: Charlie, he stuck his ass out a bus window at the girls' track team.
    Charlie: That's what you're grounding him for? When you were his age, you mooned the girls' choir.
    Alan: No, uh, when I was his age, you pantsed me in front of the girls' choir.
    Charlie: Oh, right. Well, either way, you made the yearbook.
  • Charlie, Alan, Herb and Jerome's discussions about when they first started dating, first time they had oral sex and when Gordon the Pizza Guy shows up, the names that their penises are called.
    • Jerome, Charlie's next door neighbor, meets Herb.
      Jerome: (To Herb) So how do you know Charlie and Alan?
      Herb: Oh, I'm married to Alan's ex-wife.
      Jerome: (Surprised) No kidding. And you hang out?
      Alan/Herb: Yeah./Sure.
      Jerome: Wow. I couldn't be friends with the man who was putting it to my ex.
      Herb: Well, to be fair, there hasn't a lot of "putting" lately.
      Alan: And after the baby's born, there'll be even less.
      Herb: How is that possible?
      Alan: Not only will she not let you touch her, she'll interrupt you while you're touching yourself.
      Herb: (Beat) Aaww.
      Alan: I had to start showering at the Y.
      Charlie: (Walks in) Okay, one appletini.
      Jerome: Thank you.
      Charlie: What are you guys talking about?
      Herb: Masturbating at the YMCA.
      Charlie: ...Just talk, right?
      Alan: Yeah, but the night is young.
    • Them talking about when they started dating:
      Jerome: Eighth grade, Louise Miller.
      Alan: Ninth grade, Maxine Chernakoff.
      Charlie: Sixth grade, Mrs. Terapotta. Wasn't actually a date. Nowadays she'd probably go to jail.
    • Charlie asks the guys about their first "non-traditional sexual experience." (Read: oral sex.) Herb, not realizing what Charlie meant, just says, "Boy Scouts."
    • Then Charlie asks Alan when he first took his "oral exams." Alan tries to dodge the question at first, until Herb convinces him to reveal who it was:
      Alan: Your wife.
      Herb: (Surprised) So your first time doing that was with Judith? (Alan reluctantly nods and Herb smiles) Hey, me too!
      Herb and Alan share a smile and laugh, until...
      Charlie: Me too!
      Beat. The others just look at him in shock.
      Charlie: Just kidding. Zing! Zing!
  • Herb high on pain killers at the hospital after he hurt himself when Judith's water broke and then when he sprained/broke his arm. It works thanks to Ryan Stiles' acting.

Season 7

  • Episode 3, Jake asks Charlie to drive his car.
    Charlie: You want to drive my $80,000 car?
    Jake: Yes please.
    Charlie: It's a good thing he's polite, it's a necessary quality in a doorman.
    Jake: Is that a yes or a no?
    Alan: That was a no.
    Jake: And the doorman thing was an insult?
    Alan: Yes.
    Jake: Oh.
    [Jake leaves the kitchen.]
    Alan: And a prophecy.
  • Episode 5, Charlie tries to kick Alan out of his own car.
    Charlie: That's it, get out!
    Alan: It's my car!
    Charlie: Fine, how much do you want for it?
    • Followed by Alan and Charlie are trading insults by going through the alphabet (which they call a "word game"). Especially when Charlie says Alan is a vagina, but when Alan challenges it Charlie changes it to 'vagina adjacent.'
  • Charlie joking in "Warning, It's Dirty" that since Alan's been living with him for seven years, they're a common-law couple. Legendary TV Producer Marty Pepper visits with Evelyn (She wants to sell his house.) and he lampshades the theme of the show.
  • During "Crude and Uncalled For", Charlie, Alan, and Jake get invited to one of Brad's charity functions. They get lost on the way there, and then Charlie's car dies, and they have to walk through the countryside in the dark. Jake asks whether there are mountain lions around where they are, then mentions that This Is the Part Where... it usually goes bad in slasher movies, and one guy falls behind a little, usually to smoke pot or have sex, and then he gets his head hacked off. Then he imitates a mountain lion's yowling, which makes Alan and Charlie run away screaming. Jake has a nice laugh about it, until he realizes he has fallen behind, and runs screaming after them.
  • Charlie spends an episode writing a theme song for a cartoon on Nickelodeon called Super Dad, he uses the "Super Dad" part to describe Alan's parenting when he acts like a hypocrite, then later in the episode, he gives some girl advice to Jake and does a piano riff and says "Super uncle!".
  • Charlie takes pot and ends up hallucinating past one-night stands... and ZZ Top.

Season 8

  • Charlie, after waking up on the stairs, pantsless, asks himself What Did I Do Last Night? Berta finds his pants in the mailbox, with many stamps stuck to the seat. Later, this conversation ensues:
    Jake: You didn't answer your phone and Uncle Charlie was busy trying to mail his pants.
    Charlie: You saw that? Did I happen to mention why I was doing it?
    Jake: Nope.
    Charlie: And you didn't ask?
    Jake: Over the years, I've learned to just look the other way.
    [...]
    Charlie: Oh, hey, look. There's a note in my pocket! (reading note) "Dear Inspected by #94, it is with a heavy heart that I write to you. The zipper you have signed off on has snagged my ballsack. Thank you for your prompt attention to this matter. Sincerely yours, Charles Francis Harper." Well, that explains the blood in my shorts... I hope.
    • Also Charlie wondering what he was doing that he would need his pants off but shoes on.
      Alan: Chasing a reluctant hooker?
      Charlie: (Beat) Can't rule it out.
  • When Alan and Charlie see a girl leaving the house early in the morning, Alan had this to say:
    Alan: Yours?
    Charlie: Alan, she's like 16.
    Alan: And, again I ask, hoping I won't be called to testify. Yours?
    • After the two realize that she came out of Jake's room and see a second girl come out as well, the two have very different reactions to this revelation. While Alan wants an explanation out of his son, Charlie simply congratulates his nephew.
      Charlie: Two hotties sneaking out of your room. Up top little stud!
  • Episode 2, all of Charlie's antics to get Alan to move out. Including Larry the cockatoo, sitting on Alan's toilet whilst Alan's in the shower and then getting in the shower with him.
    Charlie: Next time you drop the soap in the shower, I'm gonna forget you're my brother.
  • Episode 6, Charlie freaks out that a woman he's dating is older than him. When he tells Alan about this, he keeps trying to make himself sound younger than he is:
    Charlie: 47! That's like 10 years older than me! (Read: 4 years older)
    Alan: Why do you do that? I'm your brother; I know exactly how old you are.
    Charlie:The point is the minute I found out she was older than me, I started looking at her in a whole different way.
    Alan: And what way is that?
    Charlie: Like she's a woman who, when I'm 52, she'll be 60.
    Alan: You'll be 56.
    Charlie: What are you, the math police?
    Alan: You know what this is really about, don't you?
    Charlie: Yeah. When I'm 58, she'll be 70!
    Alan: You're really gonna keep doing this?
    Charlie: I can't help myself.
    Alan: Look at it this way: when she's 70, you're likely to have been dead for 10 years.
    Charlie: (Smiles) Actually that does make me feel a little better.
  • Episode 14, Jake and Eldridge's Jackass Expy antics.

Season 9

  • From "Big Girls Don't Throw Food" Alan finds himself back in his old room after he asks Walden if he could stay, “just a couple of days until I can find my own place,” and finds himself in a battle with Berta as to whose room this now is. Walden explains, “Yes, I told him he could stay for a couple of days,” to which Berta informs, “This guy is like genital herpes, once ya got ‘em, ya got ‘em for life!”
  • Episode 908, where Alan slowly transforms into his brother. At the end, he gets checked into a mental hospital, calls hotel room service with an imaginary phone, asks for Asian hookers, and at the end, lays back, and says "Winning".
  • Episode 909, with Alan's life rapidly becoming worse & worse after his leaving rehab. Of particular note, is Walden walking into the front lounge with Judith's daughter & asking if anyone else has noticed how much she looks like Alan, and the immediate Oh, Crap! reaction that Alan & Judith both have.
  • Zoe when high on pot brownies.
  • Kathy Bates (yes, that Kathy Bates) starring as Charlie's ghost in Alan's morphine-induced hallucination.
  • In the season finale, as Jake graduates high school & heads off to the army, he tells his worried parents "Don't worry about me, worry about our nation's enemies." After Jake leaves, a moment passes, before Walden chimes in.
    "I am worried."

Season 10

  • Walden's birthday present for Ava.
  • The "You're a Douche" musical number in Walden's head, a rare high point in the newer series.

Season 11

Season 12

  • Jake's visit in the series finale.

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