Charlie's method of punishing Jake for letting the seagulls into his house in "Big Flappy Bastards". He buys Jake a bunch of toys and video games, and then tells Jake that he's not allowed to play with any of it for a month. Quite the creative punishment.
Charlie vs. Judith's friends in "Just Like Buffalo". Jake parrots Charlie's horrible philosophy in front of Judith's friends, so she stops sending him to see Alan. Charlie misses him, so he goes to see Judith's friends, turns on his charm, and, while not actually turning them against Judith, she agrees to reinstate the original visitation schedule as long as Charlie stays away from her friends.
Season 2
When Evelyn, Rose and Berta are pestering Charlie into trying to get him to say why he hates Evelyn, he finally has had enough and delivers this amazing speech. Pity that Evelyn doesn't seem to listen.
Charlie: 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!
Jake getting an A on his history test in Season 2, Episode 14, an extra moment of awesome comes when Evelyn ends up ripping the moment away in her usual condescending way, but Alan going Papa Wolf and giving Evelyn a "Reason You Suck" Speech and tells her he doesn't want her around his son. Didn't last due to Status Quo Is God, but it was still great.
Alan telling off Evelyn for being a miserable bitch and making Charlie and Alan go to all of the effort that they put into setting up a party that she wasn't even going to bother going to. Followed by Alan flat out telling Jake to never talk to his mother like this.
The SQUAB scene is this for the Harper brothers as Jake did the one thing they couldn't do at his age. He broke Evelyn.
When Judith first meets Kandi, she spews out how she doesn't want her around Jake and Charlie and Alan call her out on her hypocrisy until she leaves.
Judith [to Charlie]: I suppose you're the one who introduced Alan to that slutty little— Charlie: Don't say it, Judith; you'll just be demeaning all women. And yes. Judith: Figures. Well, I don't want her [Kandi] around my son. Alan: Oh, oh, oh, really? So, do I get to screen the men that you're dating? And let's not forget, I know about the guy who delivered the truckload of sod. Judith: What about him? Alan:[scoffs] It doesn't take two months to put down a new lawn, Judith. Charlie: Sounds like she got laid before the sod did. Judith:[flustered] I'm not going to dignify that with a response. [she leaves] Alan:[calling after her] Watch out for crab grass!
Later, after Kandi moves in...
Judith: What in God's name does she see in him? Charlie: Well, I don't have all the details, Mrs. Harper, but apparently when he's not being emasculated and demoralized on a daily basis, he's quite the lover. Judith: What's that supposed to mean? Charlie: You know what they say, your average man's like a good field mule: if you don't beat him, he'll keep plowing all day long. Judith: Nobody says that. Charlie: You're hard to fool. [Beat] Look, I don't mean to be rude, but I'm tired of talking to you. [closes door on her]
Season 4
Charlie vs Steven Tyler. Steven Tyler wins. Also Funny Moment.
Alan: [to Charlie afterwards] The dude may look like a lady, but you fight like a little girl.
Jake winning $1120 at the track.
Alan shutting Judith up when she's nagging him about her future sister-in-law and Charlie kissing when drunk. Alan has 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!
"Release the Dogs": Jake makes Charlie promise him that he won't go out with his friend's attractive single mother, but Charlie quickly breaks that promise. Jake gets back at Charlie by first pouring slime on him (courtesy of Rose), and then luring Charlie out on the beach where he's chased by police dogs - providing the ideal catharsis for Alan, whose subconscious jealousy of Charlie has left him an insomniac.
Alan: Yessss...release the dogs. (yawns)
Alan telling Evelyn off in "I Merely Slept with a Commie" for repeatedly speaking ill of a dead woman who Evelyn isn't that different from:
Alan: Look, Mom, you have to realize that you're not that different from Cynthia. Evelyn: I most certainly am! Alan: Come on, Mom, you speak ill of everyone, even your closest friends. You, you manipulate people, you're an unbelievable narcissist, you're self-obsessed... Evelyn: That's a bit redundant, isn't it? Alan:...You find fault with everything, and frankly, I don't know anyone who enjoys spending time with you, let alone would cry at your funeral.
Season 5
Charlie Waffles' live performance, also a Funny Moment.
Jake gets dumped and gets relationship advice from Charlie. Alan's response to Judith is awesome.
Judith: Hey, honey, how's it going?
Jake: Great. Uncle Charlie's a genius!
Judith: Good, good. [to Alan] You said you talked to him.
Alan: I did.
Judith: Then why is Uncle Charlie a genius?
Alan: Because he never got married. [slams the door in Judith's face]
Charlie's plan to get rid of the woman he's seeing. Alan steals her, Charlie gives him a What the Hell, Hero? speech, convinces him to keep seeing the Girl of the Week and then Alan dumps her because she's so stiff in bed. Charlie then gets the last laugh by sleeping with a woman that Alan went out with in junior high.
After Alan drops Jake off at Judith's house after Jake disobeyed his father and stuck off to a concert, Judith chews Alan out harshly for not keeping watch on Jake and slams the door in his face ("God you're useless!"), which leaves Alan speechless instead of making his usual snarky comebacks to his ex-wife. However, after catching Jake trying to sneak out of his window again, Alan takes him to the front door, good and ready to get even with Judith over her hypocrisy.
Season 6
Season 7
Alan punching a guy who was hitting on his date.
Season 8
When Judith chastises Alan for sleeping with the mother of Jake's best friend, saying "You don't sleep with your son's best friend's mother!", Alan replies with "No, no, you marry his pediatrician."
Season 9
Winning at the end of "Thank You For The Intercourse"..and maybe even the entire episode.
Throughout "Not In My Mouth!", Jake flirts with a grown woman named Jennifer that Walden brings home, lying to her about his age. Jake and Jennifer are later left alone together when Walden, Alan, and Lyndsey leave for Paris. The closing scene reveals that Jake and Jennifer had sex. However, she remains unaware of his real age.
