Charlie vs. Judith's friends in "Just Like Buffalo". Jake parrots Charlie's misogynistic 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 the 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.
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. Shame 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 Quois 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 that 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.
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.
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: 'Cause he never got married. (slams door in Judith's face)
Charlie's plan to get rid of 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.
Alan punching a guy who was hitting on his date.
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."
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.