* George and Harold's revenge on the teachers and Melvin by becoming "Principals for a Day" at the end of ''Attack of the Talking Toilets''.
* The TakeThat comics they draw making fun of Melvin in ''Big Bad Battle of the Bionic Booger Boy'' and ''The Revenge of the Ridiculous Robo-Boogers''.
* In ''Wrath of the Wicked Wedgie Woman'', the boys trick Mr. Krupp into giving Ms. Ribble a card that says "You're one hot mama! Will you marry me?" Also doubles as a CrowningMomentOfFunny.
** Also,when Captain Underpants defeats Robo George and Harold 3000.
-->'''Captain Underpants:''' (after stealing Harold 3000's [[RocketPunch rocket arms]]) [[PreAssKickingOneLiner These'll come in]] [[StealthPun handy!]]
* As revealed in his biographical blurb, Dav Pilkey's principal as a child told him he'd never make a living as an artist and that he should stop wasting time "drawing silly comic books." Fast forward to now...
-->''Fortunately, Dav was not a very good listener.''
* ''Captain Underpants and the Sensational Saga of Sir Stinks-A-Lot'' showing [[spoiler:Harold]] as a happily-married gay man with two children in the future, is seen as one of the most progressive moments in the whole series. Even better is that it was presented in a matter-of-fact way, without making a big deal out of it.
** While this inevitably drew ire from conservative groups, as well as fans who saw that this was completely unnecessary, some of his now-adult or teenaged fans who read his books in childhood, many of whom turned out to be LGBT themselves, have practically ''exploded'' with support and happiness. Also a CrowningMomentOfHeartwarming, seeing how much it means to many LGBT teens to see an LGBT character in a children's series they loved so much.
** It's subtle, but the fact that the words "his husband" appear in the text speaks volumes about Dav Pilkey and his publisher's bravery to include an openly gay character in a children's book when such a topic is still so taboo. They weren't not doing the bare minimum of just drawing [[spoiler: Harold]] next to another man so that they can have plausible deniability if parents complained. It's right there in black and white: '''"his husband"'''.
* So many moments in ''Return of Tippy Tinkletrousers:''
** George and Harold creating quite possibly their greatest comic ever to inspire the cavemen.
** Kindergartner George saving Kindergartner Harold from Kipper Krupp & his goons by fighting them with his tie "Indiana Jones" style.
** After George & Harold change the signs at the gas station to "Free Bra Inspection," [[LaserGuidedKarma a bunch of ladies attack]] the {{jerkass}} gas station owner Billy Bill.
* The fact that George and Harold [[WordOfGod have both been confirmed]] to be diagnosed with ADHD and dyslexia, [[AuthorAvatar like Dav Pilkey]]. While it's not as groundbreaking as the whole [[spoiler: "Harold has a husband"]] thing, the fact that both kids are portrayed as smart ([[BookDumb just not]] [[BrilliantButLazy book smart]]), capable and competent as well as good kids who, while mischievous, deserve better than their school generally offers is worth celebrating as many kids with either disorder let alone both at the same time have been made to feel, intentionally or otherwise, stupid and incapable. Plus there's the fact that Dav managed to defy the naysayers who belittled his artist talents and become an ''extremely'' successful author with ''several'' successful books on the market; admittedly he doesn't illustrate all of his books ([[RickyRicottasMightyRobot Ricky Ricotta]] being a prime example) but the fact that he ''writes all of them'' indicates that he has come a long way.