After Haruki and Asahina change into the bunny-girl costumes for the first time Yuki makes Kyon pick up the discarded cloths and undergarments.
Part I: Kyon's first meeting with Mikuru when Haruhi demonstrates one of the reasons she was chosen by groping her from behind. Mikuru's whimpering only makes it funnier, no matter how wrong that sounds.
The dub has superb bloopers and delivery thanks to the English cast just being that good.Crispin Freeman in particular can do great ad-libbing, which is perfect for a sarcastic Unreliable Narrator. His various takes on the same line is one of the saving graces of Endless Eight.
One from the second episode of the Sigh of Haruhi Suzumiya in the anime counts as a Funny Background Event. An unseen kid asks their mother while the SOS Brigade are shooting a commercial, 'Momma, what's that?'. His mother's response? 'Sssh. Those are crazy people.'. Kyon's embarrassed reaction makes the moment priceless.
Shamisen, right after Haruhi granted it with the ability to talk, Kyon's conversation with the said cat suddenly becomes a deeply insightful philosophising on how beings communicate to each other with futility. Hilarity ensues.
Koizumi: You know he's got a point... Kyon: No, the cat does not have a point!
Yuki's explanations during the Mikuru Beam incident count as a deliberate joke. She stretches it waaaay out. And her pedantic corrections of Kyon make this entire scene hilarious.
Kyon: Was Asahina seriously firing beams from her eyes? Yuki: Not a particle projection cannon. Concentrated light. [...] Kyon: The problem we have here is that Asahina has been shooting off heat rays. Yuki: Not heat rays. Photon laser.
The Sigh of Haruhi Suzumiya, part five, in the anime. Itsuki's proposal to convince Haruhi the bizarre events going on lately are completely logical?
Itsuki: There is one ending that can explain any nonsensical plot...that can wrap up every little detail with ease. Kyon: Well? Let's hear it. Itsuki:It Was All Just A Dream. [everyone stares at him] Itsuki: I'm not kidding, that's the ending I was talking about.
The opening scene of episode 10 in the new season. SOS Brigade sign suddenly moving at impossible speeds during a relay race? It's Yuki. Even Haruhi has trouble believing her eyes. Koizumi's mention about the track team's likely broken spirit (as they're seen walking past behind him) makes it all the more funny.
While not mentioned much in the anime, it becomes a plot point later in the novels that the SOS Brigade was never recognized as an official club. So they shouldn't even be racing. Which makes this even funnier.
The Boredom of Haruhi Suzumiya
The Boredom of Haruhi Suzumiya
When training for the baseball episode, Yuki is sent outfield, where she expressionlessly and unerringly catches every ball about to hit her... and only the balls about to hit her.
Yuki activating "homing mode" and the subsequent home run montage.
Kyon:[small-wave] Hey. [Itsuki facepalms in the background at this]
Caterpillar-Haruhi. Caterpillar-Haruhi falling over several times, no less.
Haruhi:Let me know when your gonna wake up BEFORE you wake up!
The opening musical-credit sequence, with (dialogue-free) shots of Kyon warming up in front of the heater. Then, one by one, the rest of the SOS Brigade start jostling for room...and by the end, the pecking order is firmly established, with Kyon reduced to trying to warm himself by the computer.
Having just found Alt!Haruhi, Kyon now has to bring her to the Literature club room but has to get Haruhi to somehow disguise herself. After only a second of hesitation, he calmly asks her to put her Rapunzel Hair into a ponytail. Cue audience laughter.
The way Taniguchi turning down Kyon's invitation to the SOS Christmas party is hilarious in hindsight when it's later revealed that his girlfriend is Kyou Sou. Who mistook him for Kyon.
The Rampage of Haruhi Suzumiya
Setting up the third Endless Eight episode to be the end of the "Groundhog Day" Loop only to end it with nothing resolved leaving it to a fourth episode. Not particularly funny in the show but the reactions of people watching seems to have cemented Kyoani's Kadokawa's status as master level trolls.
Also, Itsuki's explanation of what's going on in the third "Endless Eight" episode:
One thing that made the dubbed version of Endless Eight bearable was Kyon's even more awesome than usual dialogue:
[epic voice] "Restrain thyself! Canst thou not see the No Diving sign!?" [sleepy] "The number you have tried to reach has been dis— Gah!" [juggles phone] "So, I come up behind Haruhi and say 'I lo— eeuuurgh'!" [sipping Mikuru's tea] "It's strawberry-licious!" [again, sipping Mikuru's tea] "It's so bitter, may I have another?" "My turn! I summon my 'veto' card!"
Hell, the one time his phone rings his only response is a screaming fit of Angrish
The shot of Kyon rocking out to "Lost My Music" in impeccable Deadpan Snarker style.
From the same episode, the look on Taniguchi's face upon seeing Mikuru in her maid outfit. Made even funnier in the dub where you can hear him screaming and laughing maniacally
In one scene, whilst Kyon is monologing, a bratty kid screams at a man in a teddy bear outfit for giving him a non-red balloon. His mother's response - "Shut up or I'll leave you here!"
The Adventures of Mikuru Asahina Episode 00
The Nonindicative First Episode is hilarious, but a particularly good scene from it is when Kyon's pet cat starts talking (in a manly voice, to boot, despite being a calico) and you can hear Kyon shouting off-screen for it to stop. Yuki bops the cat on the head with her "magic wand" and "explains" in a complete dead pan that she was using ventriloquism.
Mikuru firing a gun is also pretty funny as is the conspicuous Male Gaze.
Funny as it is. If you know what actually happened during filming according to the light novels, it's HILARIOUS.
Try listening to the Mikuru theme song without cracking up.
Kyon's adlib during the Koizumi/Asahina Almost Kiss scene:
Kyon: If your mouth gets any closer to her, someone standing off camera is gonna step into frame and kick yourass, dammit!
Kyon's narration after the break when Mikuru was changing clothes
Kyon: We didn't film her so don't bother asking for the footage, there isn't any.
And it's funnier because, knowing Kyon, he's probably lying.
Kyon trying to figure out plot details.
Kyon: Aaaaand... when in doubt, pan to the left.
Kyon's flabbergasted reaction after watching the film is just PRICELESS.
The Intrigues of Haruhi Suzumiya
Tsuruya spouting off innuendo at Kyon every time he shows up at her house to check on Mikiru.
The Indignation of Haruhi Suzumiya
Editor in Chief
Mikuru walks in on Haruhi sitting on top of prone Kyon, trying to rip off his jacket, jumps to the obvious conclusion, and runs away shouting apologies.
The Dissociation of Haruhi Suzumiya
Yuki (as the de facto president of the literary club) is forced to give a speech at the freshmen assembly in order to attract new members. She reads a long-winded essay titled "The Inefficiency of Language and the Transmission of Data." Translation: "This is all a waste of time."
The Surprise of Haruhi Suzumiya
Kyon has to go back to the clubroom to meet with Yasumi, and he needs an excuse to say to Haruhi. So he tells her, to her face, that Taniguchi had lent him a rare porno magazine, and there'd be big trouble if it were discovered in his desk. Haruhi is left speechless.
After the climax, Kyon is randomly bouncing around in time. First he ends up a few years in the future, at Haruhi's college, where it's strongly implied they're going to the same school and possibly dating. The real crowner, though, comes when he ends up a month in the future, in Haruhi's room. In the middle of the night. In her bed, ON TOP OF HER. And let's not forget who sent him there in the first place: Haruhi. Subtle, that girl is not.
Kyon: If you insist upon having Asahina-san dancing [for the concert], I have an idea of my own. Haruhi: What kind of idea? Spit it out! Kyon: Starting today I will call you Haru-Haru. Haruhi: Gah! Kyon: Are you still OK with it? Well, Haru-Haru? Yeah, Haru-Haru? Say something Haru-Haru. Haruhi: B-Bastard!!! Koizumi: Feel free to call me Icchan. Kyon: Nobody's talking to you! Koizumi: I see. Nagato: Yuki-rin. Kyon: D-Did you say something, Nagato? Nagato: No.
Each time Kyon Squees over Mikuru is funny. "SO CUTE!"
A minor one, but the English translation of the fifth novel has Tsuruya address Haruhi as "Harls".
Some of Kyon's narrations are pretty damn funny, especially his "No, but my danger sense was tingling." after Haruhi stares at him.