- George and Harold's revenge on the teachers and Melvin by becoming "Principals for a Day" in Attack of the Talking Toilets.
- The Take That comic they draw making fun of Melvin in Big Bad Battle of the Bionic Booger Boy.
- 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 Crowning Moment of Funny.
- Also,when Captain Underpants defeats Robo George and Harold 3000.
- 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 Harold as a happily married gay man, is 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, 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 Crowning Moment of Heartwarming, seeing how much it means to many LGBT teens to see an LGBT character in a children's series they loved so much.
- George and Harold creating quite possibly their greatest comic ever to inspire the cavemen in Return of Tippy Tinkletrousers.