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  • 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 Take That! 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 Funny Moment.
    • Also, when Captain Underpants defeats Robo George and Harold 3000.
    Captain Underpants: (after stealing Harold 3000's rocket arms) These'll come in handy!
  • As revealed in his biographical blurb, Dav Pilkey's teachers and 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.
    • Speaking of which, a fan asked Dav on Instagram if he ever saw said teachers or principal again after the success of the Captain Underpants series, and this was his response:
    “No, I never saw any of them after my books started coming out. I had a few opportunities to, but I declined. Sometimes it’s best to put the past behind you. #nohardfeelings #noregrets”
  • Captain Underpants and the Sensational Saga of Sir Stinks-A-Lot showing 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 matter-of-factly, without making a big deal out of it.
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    • While this inevitably drew ire from conservative groups, as well as fans who felt that this was completely unnecessary, some of his now-adult or teenage 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 Heartwarming Moment, 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 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".
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    • This development was so well-received that Harold/said husband has been adopted by the entire fandom as definitely the future (At worst, he and Harold will be in a triad with George, which may or may not also involve George's wife, who is well-liked if not to the extent of Harold's 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
      • First George outwits the jerkass gas station owner Billy Bill by changing the station sign to "Free Bra Inspection," and a bunch of ladies attack the rude gas attendant.
    George: Ya gotta learn to stick up for yourself, or people will bully you your whole life!
    • George then standing up to the bullies by whipping them with his tie "Indiana Jones" style.
  • The fact that George and Harold have both been confirmed to be diagnosed with ADHD and dyslexia, like Dav Pilkey. While it's not as groundbreaking as the whole "Harold has a husband" thing, the fact that both kids are portrayed as smart (just not 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 artistic talents and become an extremely successful author with several successful books on the market; admittedly he doesn't illustrate all of his books (Ricky Ricotta being a prime example) but the fact that he writes all of them indicates that he has come a long way.
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