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Funny / Harry Potter and the Natural 20

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  • This:
    "What's Quidditch?" Harry, Hermione, and Milo asked simultaneously. Ron fainted into his pudding.
  • Sure, it fires off right as Milo is trying to sneak away from a troll, but the fact that Hermione pranked Milo was hilarious.
    Watch enchanted by Hermione: Milo's got a da-ate! Milo's got a da-ate! Don't be late, don't be late, 'cause Milo's got a da-ate!
  • Milo's entire misunderstanding over Elves / House Elves, Father Christmas, Santa Claus, etc.
    "Milo wasn't sure exactly what this Father Christmas's connection was to the Drow in the kitchen that tried to poison him..."
  • Milo shows off his protectively enchanted robes to Harry by having Harry stab him with a dagger. When it fails to cut the robes, Harry decides that he needs to check the dagger's sharpness... by cutting a few other things. Like his window curtain. And Ron's window curtain. And his bed. And Ron's bed.
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    • And the whole time he's doing this, Milo's listing all of the things he could have used the XP that went into the robes on.
  • Otiluke's Razor: "the most dramatically appropriate solution is usually the best one."
  • This statement of Milo's:
    "Fortunately, the whole Ministry's probably not in on it, or there would be all sorts of signs: wrongful imprisonment of sympathetic characters, horrific beings of death and fear in their employ, mysterious rooms in their basement full of gateways to evil dimensions, disagreements with Dumbledore, that kind of thing. Also, probably spikes on the Ministry roof—hey, Ron, your dad works there; has he ever mentioned spikes on the Ministry roof?"
  • Hermione, Deadpan Snarker:
    Milo: "For some reason, your world calls Medusas Gorgons. What do you call your two-ton, eight-foot wrought-iron cows then? Pixies?" "Dolores Umbridge," Hermione answered, completely straight-faced.
  • Snape's first lesson. They got to Snape's second question to Harry, and then the paranoid (because Snape looked evil to Milo) and expecting ambush (have we mentioned that Snape looked evil?) Milo snapped and used Glitterdust on Snape and the slytherin students.
  • The final to their fight again Quirrell. "Anticlimactic" is the word we are looking for.
    Harry: "Did ... did Voldemort just finish himself off?"
    Milo: "Bit anticlimactic, if you ask me."
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  • Milo trying to make Vernon Dursley treat Harry better. It started with Milo appearing on the Dursleys' dining table—high-speed arrival via Dimension Door, with a sword in his hand—while the Masons were arriving. A short conversation later, and we had a listen-and-repeat event between Milo and Vernon, one that quickly devolved into something ... deranged for people who aren't Dungeons & Dragons characters.
    Milo: "And I will guarantee that he eats the same food we do."
    Vernon: "And I will guarantee that he eats the same food we do."
    Milo: "And I will give him his fair share of the loot"
    Vernon: "And I will give him his fair share of the loot"
    Milo: "Where 'fair share' is defined as 'one over the number of people involved'"
    Vernon: "Where 'fair share' is defined as 'one over the number of people involved'"
    Milo: "And I will pay any and all gold necessary to Clerics to cure Harry in the event of injury or death."
    [ ... ]
    Vernon: "And I will actively prevent glass cannons from achieving a flank position on Harry through appropriate deployment of tanks and battlefield control."
  • Crabbe and Goyle and Malfoy are ridiculously funny here.
    Draco: Do you know what day it is tomorrow?
    Crabbe: Uh, Thursday?
    Draco: No! Well, actually, yes. Tomorrow is Thursday. But that's not what's important!
    Goyle: Uh, Friday?
    Draco: No! Wait... what? Look, Goyle, I just said that tomorrow is Thursday. Surely even you... I mean, really?
    Goyle: Well, you also said it wasn't what was important, so I thought, maybe the important thing about tomorrow is that, while it's Thursday, it's really Friday. You know?
    Draco: Uh, No... not... really... Look, guys, we're getting off topic. It's not about the day of the week, okay?
    Goyle: Oh! Oh! I love this game. Is it smaller than a breadbox?
    Draco: Uh. Well, kinda, I guess, in an abstract sort of sense, tomorrow is bigger than a breadbox... wait, no! We're not playing Twenty Questions! Just... just... just guess, okay? It's like, really obvious. Here's a hint, even. Today's the Thirtieth of October, so tomorrow is...
    Crabbe: Friday!
    Draco: You're fired. You're both fired.
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    • Apparently, they take after their fathers.
  • The omake between Chapters 26 and 27. It's a crossover with Harry Potter and the Methods of Rationality. After Harry explains the basics of the laws of physics to Milo:
    Milo: And this—honestly, you have to swear that you're not pulling my leg here—is seriously how this Plane works?
    Harry: Pretty much. It's a good deal more complicated than that, but we have to start somewhere.
    Milo: Because, well, I'm pretty sure I can get around that.
    Harry: Around what?
    Milo: All of it.
  • Dumbledore's Big Damn Heroes moment in Harry Potter and the Save-Or-Die is not only awesome, but hilarous as well. He shows up just in the nick of time to save Milo from the Killing Curse, while pretending to be a tour guide that had taken a wrong turn.
    Dumbledore: And here we have the famous third lower janitorial closet, considered enormously significant among janitorial historians due to its—oh, pardon me. This isn't the third lower janitorial closet at all. In fact, unless I am quite mistaken, these are the long-unused Department of Magical Law Enforcement interrogation cells. Not to be re-opened except in times of war. Clearly, there has been some misunderstanding.
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