During the duel between Roy and the Reaper, the Reaper kicks Roy, despite not having legs. When asked how this is possible, the Reaper just shrugs.
Ryoji, while explaining The Fall, tells the SEES that they can't stop the end of the world. Roy narrates how everyone looks scared or angry, but in particular notes Akihiko's reaction.
"Aki's just scowling like it's an Olympic Event."
Hades is described by Shinjiro in the exact same way in Answer of Aeon, though the situation is much more fitting, and overall more serious.
Shinjiro has a brilliant deadpan snark after recovering from his coma and being caught up on the story's events.
"I get shot and end up in a coma for two months, and you guys manage to bring about the apocalypse? Geez Aki, didn't I tell you to take care of them?"
The entire pirate sequence during the Yakushima vacation arc.
In Reshuffled, Pharos at one point jumps up and down in front of Yukari's face because he's invisible to everyone but Roy.
Roy and Yukari on studying up on the ghost story. Yukari is going to keep researching even though Roy's not into it.
Roy: "Alright, just tell me you'll stop before you start looking into Tomes of Eldritch Lore."
Yukari: "...I make no promises."
A serious situation, but Shinjiro's summary of his big accident is funny when reduced to Beige Prose:
"Alright, I screwed up in the Dark Hour. My Persona went nuts when I summoned it. Shit happened. I'm not going back. Happy now?"
A short time after being confronted by Naoto, Roy casually tells Junpei:
"You do know the short one with the hat was a chick, right?"
"HULKSTER'S GONNA RUN WILD ON YOU!"
Captain Meathead Mc Protienboxer
Shinjiro's subsequent laughing fit. Made even funnier when his aunt and uncle don't seem too surprised by the event, simply commenting that it's been a few years since this happened.
Additionally, Akihiko is afraid of spiders. Not only is Roy's Persona Anasi a spider god, but he gets a pet tarantula in chapter 21. Needless to say, his reaction is priceless (and leads to another laughing fit from Shinjiro.)
"Seems his ability to act tough and intimidating just flies right out the window when he's laughing that hard."
The Crossdressing Pageant. Full Stop. Between Hamuko and Junpei - somehow - managing to win spots as Emcees - Dressed up as Jack Frost and Pyro Jack respectively - to Akihiko somehow being part of it, to the random student who wins it in a lovable nod to everyone's favorite blue bear
Really, the whole culture festival counts; the two junior classes pooling together to make a maid cafe - Shinjiro as the chef of all things - the Featherman stunt on day two, which also should count as an Awesome Moment,, the subsequent stealing of a prop from said stunt that involves Yakety Sax ... All that was missing was a visit from the Velvet Room to make the insanity complete.
