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Anime & Manga
- Rukia in Bleach is known for loving to draw Chappy the Bunny, being absolutely horrible at drawing, and using her bad drawings to explain concepts with different people being different colors of bunny. Most of the other characters are never really sure what her drawings are supposed to be.
- The exception is Aizen. She draws him as a bear.
- In Kyo Kara Maoh!, nobody ever figures out what Gwendal's knitted animals are supposed to be.
- In Azumanga Daioh, not even Sakaki can identify what species her knitted dolls are.
Sakaki: "That one's a dog, and that's a cat... Or is it the other way around?"
- The Strawhats' second ship in One Piece looked like a lion, made by Franky. But everyone else thought it looked like a sun or a sunflower. Franky even intended to name the ship Lion Gang Champion though in the end everyone else went with the Thousand Sunny instead.
- In an episode of Ranma ½, Akane bakes some cookies for Ranma in a variety of animal shapes, but the results come out so poorly that Ranma's guesses at identifying them are completely off the mark, with Akane getting increasingly incensed each time she corrects him (she eventually gives up: "Are you gonna keep guessing or just eat them?!").
- At another time, she sewed a "cute" patch on Happosai's gi (which, unbeknownst to him, contained a "Woman Repellant" scent.) Happosai is delighted at the "cute little piggy," which a flustered Akane claims to be a dog.
- And yet another time, Ranma, Akane, and Ukyo try to pacify a rampaging (and ugly as sin) divine horse by drawing a flattering portrait of it . Ranma and Akane's attempts are so terrible that Miss Hinako tries to guess whether they're drawings of shrimp or bugs.
- In Victorian Romance Emma, little Colin Jones draws doodles that look vaguely like some animal or other and gets upset if they're misidentified. Eldest brother William is the best at figuring out what's been drawn, mostly because every other Jones child once drew like that.
- The "What a horrible ugly monster! It's a picture of mommy..." variant is used in Le Chat, a Belgian comic.
- In The Little Prince, the narrator explains how he once drew a picture of a snake that had swallowed an elephant, and all the adults told him it was a very nice hat.
- In The Baby-Sitters Club, it is suggested that one say something along the lines of "What a nice picture! Can you tell me about it?" when confronted with a child's drawing, because "you don't want to say 'what a lovely elephant!' and have it turn out to be a picture of their grandmother."
- In Just So Stories "How The First Letter Was Written", written language was invented to avoid this sort of confusion, after a picture intended to convey "Daddy has broken his spear, he needs his spare one, and this man who doesn't speak our language will bring it back" was interpreted as meaning "Daddy is being attacked from all sides by men with spears".
- In the Eighth Doctor Adventures novel Camera Obscura, everyone who sees the Doctor's attempted map of a London neighborhood wonders about the round shapes he's drawn. Fitz tries to guess what they might be ("trees", "gardens", or "duck ponds") until Anji gets annoyed and sarcastically suggests they're "gigantic pools of jam". Oddly, Fitz and Sabbath both describe them as "puffy". It's never explained what they were actually meant to be.
- In Nation, Daphne/Ermintrude sends Mau an invitation to join her for dinner. She writes it out, then, in case he can't read, draws a picture of a stick figure with an arrow pointing towards the boat. Mau interprets it as meaning that, when the sun is at a certain angle in the sky, he's supposed to throw a spear at the boat.
Live Action TV
- Played with in Stargate SG-1. Daniel and Sam are presented with a thermal image of the symbiote inside of Teal'c, and they play dumb:
Daniel: Oh, that's very good! Did you draw that yourself?Sam: What is it?Daniel: That... That's a duck, isn't it?
- From Criminal Minds. Morgan looks at a picture drawn by an autistic kid and can't figure out what it is. Hotch makes a glance, says "It's obviously a dog" and keeps on with what he's doing, leaving Morgan absolutely befuddled.
- The game show Win, Lose or Draw was basically a game show version of Pictionary. Coincidentally, there were also two official game show versions of Pictionary, but neither was as popular.
- Pictionary is played in Community episode Basic Genealogy and the game devolves into a fist fight when an attempt to draw a windmill looks more like a swastika.
- In one episode of Ned's Declassified School Survival Guide, Ned tries to paint abstract art and the entire school thinks it's a naked lady. At the end of the episode, he actually tries to draw a naked lady and people see it as a fire truck.
- In one episode of Engine Sentai Go-onger, the heroes are stumped, trying to think of a way to defeat the Monster of the Week. When it's Gunpei's turn to offer an idea, he starts his explanation with a drawing of... something.
Sosuke: What's that?Saki: A koinobori? noteHant: Nope, it's a log.Renn: I'm sure it's UMA.note [gets stared at] UMA is...Gunpei: (exasperated) It's a PENGUIN!The others: No way! This is a penguin?
- One episode of The Bill Engvall Show has Paul with a sculpture of himself, only for it to be mistaken for one of Don Cheadle.
- The Friends good-naturedly mock Monica for the horrifying "Pictionary Incident," wherein she threw a plate in a moment of frustration at one of her buddies' poor drawing. She insists she was just gesticulating forcefully and the plate slipped out of her hand.
- In one episode of The Big Bang Theory, Leonard, Sheldon, Amy, and Penny have a Game Night, girls vs. guys. They start out with Pictionary, and Leonard and Sheldon completely fail at it. (Sheldon mistakes 'polish' for 'Polish', so draws Polish sausages and things associated with Marie Curie and Copernicus, who were both Polish. When it's Leonard's turn to draw, Sheldon guesses science things like 'quark-gluon plasma', when it's actually a chocolate chip cookie.)
- German family show "Die Montagsmaler" was entirely based on invoking this trope - A had to scribble a pic illustrating some word and B ("Hund! Katze! Maus!") had to identify it. Crowning Moment of Funny ensued when a completely inept contestant should draw a navel - and the guesser refused to solve, thinking it was, uhm, something less innocent.
- A For Better or for Worse comic has a young Elizabeth showing her father a painting after a day of preschool. Her dad starts to comment on what a nice face it is, until Elizabeth interrupts to tell him that it's just a pizza.
- In a FoxTrot strip, Roger and Andy are playing Pictionary. He keeps shouting out obviously incorrect answers as the drawing progresses (including "It's a snowstorm!" before she's even drawn anything), culminating in "It's a Christmas tree in a cereal bowl next to a snake!" and "What's with these 'B', 'O', 'A', and 'T' symbols? Are they Pictionary shorthand?"
- The Chapel Chronicles, in a reversal of the usual trope, Chapel draws an photo-realistic Mona Lisa, but her opponent Fred can't identify it.
- In Homestuck, Jade Harley owns a Pictionary Modus. It misidentifies an advanced bass for a mecha, the Tangle Buddies for a pair of gloves with some coins and the Magic Cue Ball for the Magic 8 Ball.
- A skit from The Whitest Kids U' Know has a child showing a picture he drew to his parents. While it appears to be something rather inappropriate (read: penis), he explains to his parents after they fail to recognize that it is actually an elephant. Subverted moments later, when the child shows them a drawing that looks exactly what it meant to be.
- Family Guy
Peter: Stewie, uh, how long you been all messed up and evil like this?Stewie: Oh, so now you're interested in Stewie. Last week when I made that macaroni picture of an owl, you didn't give a damn!Peter: That was an owl?
- "Lois Kills Stewie":
Stewie: It wasn't right the first time you said it! Why the hell would it be right the next ten times?!
- Another episode features Stewie actually playing Pictionary with a family who had moved into the Griffins' house. The husband of the family keeps shouting, "It's a jackal! Jackal! It looks like a jackal! Jackal!", much to Stewie's irritation once time runs out.
- In Avatar: The Last Airbender, this happens to Sokka several times.
- The Simpsons
- In "A Milhouse Divided," the Simpsons host a dinner party with a game of Pictionary. Maude Flanders guesses "cornstarch" from three dots drawn by Ned, while Kirk Van Houten is unable to draw "dignity," though Luanne is. Homer thinks that Kirk is also unable to draw "a door".
- In "You Kent Always Say What You Want", Maggie and Marge play some amazing rounds of Pictionary against Selma and Patty, but despite Maggie's drawings being incomprehensible, Marge always knows what they are.
- The Penguins of Madagascar: Julien and Marlene are missing and Kowalski shows a picture he drew of them to Fred the squirrel.
Fred: Which one's the otter?Kowalski: This one, obviously. Note the whiskers?Fred: Oh, I thought that was a cat.Kowalski: Did I ask "have you seen this lemur and cat?"Fred: No, that's why I thought it was odd that you drew a cat.Kowalski: It's not a cat.Fred: Then why does it have whiskers?Kowalski: You know what? Forget the otter.Fred: Cat.Kowalski: Whatever!
- Happened in The Grim Adventures of Billy & Mandy in a episode in which Dracula's pictionary drawing of Abraham Lincoln is mistaken for successively more absurd things.
- A variation in the Phineas and Ferb episode "Put That Putter Away": Candace apparently has such poor handwriting that when she writes the word "busted" on a piece of paper, both Stacy and Phineas mistake it for a drawing of dancing weasels.
- Parodied in the Rocko's Modern Life episode "Cabin Fever". Bev Bighead invites Ed to try hand shadow puppetry with Rocko and Heffer, and despite Ed being able to create the unmistakable shapes of "The Thinker", the Eiffel Tower, and a prancing deer, none of the other three can get anywhere close to the right answers. This raises Ed's temper to the point that he causes the Hair-Trigger Avalanche driving the remainder of the episode's plot.
- In Animaniacs, the Warners play Pictionary with Pablo Picasso. The Warners are unable to decipher his realistic drawings, while their weird-looking doodles leave him flummoxed. When an art dealer arrives and sees the Warner's drawings, he mistakes them for Picasso's and praises his new "Cubist" style.
- O'Farrell's attempt at assembling a sketch of the serial shredder in Fillmore!:
Tehama: Okay. What the heck is that?
Fillmore: Uh, no offence, Danny, but that kinda looks like Tiger Woods on a very bad morning.
Ingrid: (squinting) Oh yeah, and that's his elbow...at least, I hope that's his elbow...
- In the Jimmy Two-Shoes episode "The Big Date", one of the things Jimmy and Beezy try to do to keep Jez busy while Lucius deals with a problem at his factory is the trope. Hilariously, Jimmy draws an extremely accurate horse representation but Beezy constantly identifies it as things like a waffle.