Funny / Cromartie High School
Freddie. Just Freddie, and everything involving him, such as him giving perfect directions inside a city when using an old world map that has the USSR in it!
Well, There's also just about every bizarre moment that warps the viewer's brain...which would be pretty much every moment after the five-second-mark of the first episode.
In the fifth episode, when Kamiyama accidentally sits on Takenouchi's lap.
Takenouchi: I wanna tell this guy to get off of me, but if I open my mouth, then I'll hurl.
Kamiyama (moments earlier): I'm being so disrespectful...I need to take off my hat.
Kamiyama also mistaking Takenouchi's motion sickness for, well, this:
You're obviously pale and weak because you haven't eaten anything. Here, have this pudding!
(One has to wonder just where he got the pudding from, since he obviously didn't have any bags or containers of any sort on his person before or after that moment - and how it made Takenouchi faint.)
Kamiyama said that the pudding was warm. That probably sent Takenouchi over the edge.
I forgot to mention the gorilla(s). Yeah...just watch it and everything should make perfect sense...if you're high.
Pretty much all of episode 6, especially the forest moment: "Oh my god! This is a non-sequiter!"
Fujimoto's encounter with an internet troll, which ingeniously utilizes three different forms irony for one truly hilarious moment.
The movie's chock full of this too. Especially the part where Uchuu Genjin Gorilla plays. And the final battle, complete with sound effects ripped from Starcraft or AOE.
Also from the movie:
Kamiyama: Don't be so selfish Hayashida. We're going to give these drugs to all of the needy children in the world!
Seven Hours Later, in a jail cell,
Kamiyama: I thought we were doing a good deed...
HE ATE MY PENCIL!
The entire first section of the final episode because of the gender swap.
"Faggots". The delivery is perfect.
The "random pictures" Hayashida sends to Maeda, culminating in a series of his date with a mystery girl ( Maeda's mom).
"Holy crap! I've got the body of a seal!"
The finale of the manga is this, as the last page announces out of nowhere that the manga has ended. Interestingly enough, it says that the creator only found out his series was discontinued when he went to a store to read it and found out it had been cancelled for TWO WHOLE MONTHS without him finding out.
In episode 17, there's an insanely random and hilarious visual gag when Takenouchi talks to Hayashida about his motion sickness problem. The two drink glasses of ice water as they talk, and after Takenouchi admits his problem, it cuts to a shot of Hayashida. For no reason, his glass of ice water is now gigantic and he's holding it with two hands. Then in the next shot, it's normal again.