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  • Equal parts Funny and Tear Jerker, this conversation.
    Vanessa: "Milo, why are you going to bed so early?"
    Milo: "So that tomorrow will come faster. Today is boring!"
  • When Milo sees a pregnant cat hiding in the bushes.
    Milo: (to Vanessa) "Did you hide when you were pregnant with me?"
  • When Milo is ticked at the fact that Judith was singing that he was too small (to touch the clouds).
    George: "We're all a little too small to touch the clouds."
  • Milo telling Lucas's mother that he might be Lucas's soccer coach. Lucas is a baby.
  • When Vincent, Thomas and Milo prank Victor with a squirty flower (or "water him" as Thomas puts it) and then surprise him with a jack-in-the-box. Unlike some pranks on the show, he finds this funny too.
    • Speaking of funny pranks, the April Fools jokes of putting fake fish on each other's backs and the fake substitute teacher.
      Teacher: "Today, students, I will teach you to walk up walls like a lizard, walk on the ceiling like a spider and fly...well, like a fly. It's very simple. Just observe these creatures very closely and imitate what they are doing."
  • This part from "The Infirmary".
    Doctor: "I'm a doctor. Why do you have to do as I say?"
    Milo: "Because our teacher makes us."
  • Even though it was a bit Nightmare Fuel-y, Milo nearly eating toadstools, what he says afterwards is funny.
    Milo: "You mean they look pretty, but it's to fool you."
  • Milo and George thinking the dippers (constellations) look like shopping carts. Then there's this line.
    Milo: "Who's big enough to drink from them?"
  • If you don't mind a bit of Toilet Humour, this scene from the otherwise quite serious "Shame" was quite funny despite what it led up to.
    Judith: *shows her drawing of a field with a bush to Milo*
    Milo: *draws a white dog near the bush* "Look. Now there's a dog in the picture."
    Judith: *draws a stream of pee from the dog* "Look *chuckles*! It's peeing!"
  • Even though the scene of Judith sulking in "Judith's House" was a Tear Jerker, this line from Milo to try and cheer her up was funny.
    Milo: "We could play cards...and I'll let you beat me."
  • When Milo finds chocolate eggs.
    Milo: "Oh, great! Here's one." (finds another) "Double-great!"
  • In "The Spelling Lesson", Milo sharpens his pencil twice, leading to this.
    Milo: "I've become an expert pencil sharpener!"
    Thomas: "Here you go, Mr Pencil Sharpener. Sharpen my pencil."
    Elise: "And mine too, please."
    Milo: (waving pencils in the air) "Come one, come all. I'll sharpen all your pencils! Every pencil in the world. I'm the best pencil sharpener in the whole wide world!"
    Thomas and Elise: (laugh)
  • This part at the end of "The Spinning Top", when the teacher spins Milo's spinning top as she gives it back to him.
    Milo: "You're not allowed to play in class, teacher."
  • In "Milo and the Attic" when Milo imagines (we don't see his imaginings but we hear about them) that the things falling down was a trap to prevent him finding treasure.
    • From the same episode, thinking that the photo of George as a little boy is of him because they look similar (due to being related).
      Milo: "That can't be you, Dad. You're not a little boy."
    • When George says that the spaceship toy is his.
      Milo: "But it's a toy. Daddies don't play with toys."
  • In "Milo and the Spider" when Milo is pretending to be a wolf and pretends to eat a bit of his mother Vanessa's hand.
    Vanessa: "The little creature is eating the big creature. I've never seen that before."
    • Which leads to this when Vanessa is startled by the spider nearly landing on her.
      Vanessa: "Don't be scared, Mommy. The little creatures don't eat the big ones."
  • During "Milo and the Goldfish", Milo making faces at the goldfish and pretending he's a shark or a sea monster.
  • This part of "Something's Fishy"
    Judith: "Let's fish like polar bears. It'd be less disgusting than using those worms."
  • In "Milo and the Little Mouse", Milo tries to fool the Tooth Fairy by putting a pebble under his pillow instead of a tooth. That's funny enough on its own, but even more hilarious is his letter.
    Milo, you have to be patient about these things and don't bother putting pebbles under your pillow instead of teeth.—Tooth Fairy.
  • In "Happy Birthday Mummy" when Milo tries to pay with play money.
  • In "Sew Happy", when Milo and Judith play progressively more evil characters in their dress-up game: Judith plays an evil witch, then Milo plays a bear, then Judith plays a bunny-eating snake, then Milo plays the "evil foot giant".
    • At the end, Milo suggests that if he were a wizard, he could just use magic to take the makeup off of his and Judith's faces.
  • When Milo finds out what a lifeguard is in "Seashells and Sea Creatures".
    Milo: "A guard? What for? Does he guard the crabs?"
    • Also from "Seashells and Sea Creatures", when Milo sees the low tide.
      Milo: "We're here...but where's the sea?"
  • In "The Little Bear", when Milo's class is on a camping trip, sleeping under the stars and before going to bed, they look up at the sky and the teacher says they can see animals up there. She's referring to constellations, but the children think she's saying there are literal animals in the sky. Vincent says they'd need wings and Judith says that they could have traveled in a rocket.
    • There's also Milo finding out that the galaxy is called the Milky Way.
      Milo: "The Milky Way? You mean there's milk up in the sky?!"
    • When Milo dreams that the bear constellations have come to life and are drowning in the Milky Way, then he wakes up and remembers they live in the Milky Way and are not in danger so they must have been tricking him. Extra funny as he says, "That was a good one."
  • "Milo Goes to the Beach"
    • When Milo wears sunglasses for the first time.
      Milo: "The beach looks totally different!"
    • And when Vanessa puts sunscreen on him.
      Milo: "You're buttering me like a piece of dough."
    • The fact that Milo refers to the kite he chases as "Mr. Kite" and calls it "him" rather than "it".
  • All the animal jokes that Milo and George make in "Milo Visits the City".
    • Milo pretends that cranes are giraffes.
      Milo: "Look. A herd of giraffes!"
      Judith: "Don't worry. Those are totally harmless."
    • George calls a truck an "elephant" and Milo thinks its fumes smell bad.
      Milo: "Wow. That elephant really stinks, someone needs to give it a nice hot bath."
    • George calling the traffic lights "chameleons" because they change colour, which leads to a line that would not make sense out of context.
      Milo: "We can't cross here. There are no chameleons here to help us."
    • George calling the stripes on a pedestrian crossing a "secret code" and saying it's a zebra's stripes. Then Milo states that he hopes it doesn't hurt the "zebra" when they walk on it.
    • George calling a man on a motorbike (or the motorbike he was riding, or even both), a "panther". Then Milo says that the "panther" roars loudly.
    • Milo in a quiet area of the town.
      Milo: "The jungle's gone quiet."
    • George stating that a safe area was "for jungle adventurers only".
  • At the end of "Sticking Together", when the teacher delivers the show's Aesop about how you should watch out for the rest of the group while in a group, she says that she "doesn't have eight pairs of eyes", leading to this.
    Milo: "Eight pairs? That'd be funny! You'd fit right in here at the zoo."
  • In "Teacher's Helper", when Vincent is imitating a fly despite Milo (who's filling in for the teacher while she runs an errand) telling everyone to be quiet. It leads to this conversation, which sounds weird out of context.
    Vincent: "I can be a fly if I want to."
    Milo: "You're not a real fly!"
  • In "Teacher For a Day", Milo interrupts his teacher so the teacher lets him teach the lesson. This leads to this.
    Milo: "Well, the old castles are made of stone and they—"
    Vincent: "Keep all the knights' armor there?"
    Milo: "Well, yes, but a long time ago—"
    Vincent: "Whaddaya mean a long time ago?"
    Thomas: "When there were dragons?" (flaps his arms)
    Mario: (laughs)
    Milo: "Well, no, uh..."
    Judith: "Dragons like in fairytales?"
    Milo: (looks confused)
    Judith: "And kings and queens and princesses?"
    • Which is followed by the whole class chatting to each other and you can see in the background that Thomas is flapping his arms.
    • When the class are trying to find the word for "loopholes". Vincent thinks it's "shoeholes" and Judith thinks it's "pieholes".

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