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Panty: Uh oh~! Peekaboo! I saw it. There it is...there it is again. Hello! Still there. Fatty! Fatass! One more hip! Fattyfattyfattyfattyfatty...
Stocking:Ohhhhhhh-hohohohohoho~! Chuuuuuuuck, come heeeeeeere~! [takes Chuck to the elevator while twirling to beat the shit out of him] SPIT IT OUT RIGHT THERE OR I'LL GAG YOU WITH A TOOTHBRUSH AND EAT THE CHUNKS LEFT OVER FROM EVERY DONUT HOLE YOU'VE STOLEN FROM ME IN THE PAST 48 HOURS! [Chuck pukes] TRY AGAIN!
Panty making good on her promise to laugh if Stocking got fat from all the cake she was eating.
Brief's reaction to Garterbelt coming back to life: he screams/gasps in a manner that sound more like a goofy laugh, which really sounds nothing like how he normally sounds.
The end of Episode 13. Stocking kills Panty and Garterbelt (who unexplodes again), and walks away with Corset. Cue Garterbelt, Brief, Chuck and the Demon Sisters staring blankly for a good five seconds, with appropriately hilarious facial expressions.
Which goes to show, Gainax might be the only studio to troll their own characters.
The death of Sam, simply because of how ridiculously over-the-top it is.
In "...Of The Dead," when Panty and Stocking beat the hell out of a zombie cat with a pair of brightly colored dildos, while saying this little gem.
For all the flack it gets from purists/weeaboos, the dub version is actually pretty funny when you actually give it a chance. Jamie Marchi and Monica Rial make both Panty and Stocking sound hilarious, and still fairly true to their original characterization.
As good as the English dub is, there's one thing from the original Japanese it can never recreate: the Gratuitous English cursing with heavy accents. It adds a level of hilarity impossible to get otherwise. Exhibit A
In Episode 2-B, "Sex and the Daten City", Panty and Stocking are searching for copies of Panty's porn flick to destroy them. Where are some of said copies? In the mouth of a camel in Egypt, in Antarctica and on a space station (the last for educational purposes).
The History of the Earth, according to Garterbelt. While the animated sequence is funny, Garterbelt being in for several famous paintings and photographs is the best part, especially because he was an African-American Ku Klux Klan member.
A meta example: At Shutocon 2014 in Lansing, MI, Jamie Marchi, Monica Rial, and Ian Sinclair conducted an 18+ Q&A panel whilst in-character.
1.) This meant that Ian answered a lot of dirty questions with Chuck's signature Poke-Speak and suggestive hand gestures.
2.) Then, somehow, the panel dissolved into Panty and Stocking discussing their cakesitting/cakefarting preferences. (Italian icing for the seal, asparagus cake as not to waste a cake that tastes good).
3.) Ian Sinclair didn't know what it was and had to Google it on his phone. He promptly declared "Chuck-chuck CHUCK?!" and stormed out of the room!
4.) He struck a pedestrian when he kicked open the door.