Just because Misterland (Happyland especially) is one of the happiest places in the world doesn't mean sad things don't happen to the Mr. Men and Little Miss.
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General
- Anytime Mr. Happy and Little Miss Sunshine get upset is tearjerking.
- Whenever Little Miss Shy and Little Miss Tiny cry. Their crying really punctuates how upset they are over what happened.
Books
- The fact that Mr. Uppity was Hated by All due to his Rich Bitch behavior to the point where he was living by himself in his own house and the citizens even call him "Miserable Old Uppity" everywhere he goes. That's not to say they weren't wrong but still...
- Little Miss Giggles crying over losing her ability to giggle, she even contemplates changing her name.
- Mr. Quiet's life prior to moving to Happyland is pretty sad to read about, he is basically unable to go shopping in Loudland due to the Loudland residents not being able to hear whispering. He is heavily implied to be malnourished as a result of thisnote , to the point that his supper at Mr. Happy's is described as his first proper meal in months.
- Little Miss Shy is so quiet and shy that she spends most of the day in her own garden, is afraid of talking to people, and only goes to the party at all because Mr. Funny escorted her.
- Little Miss Tiny lives in a mouse hole instead of a house, is scared of large animals, and wishes she has somebody who notices her and who she can talk to.
- Mr. Good's life in Badland is pretty sad. He lives in a place where everybody is mean and cruel, and doing good deeds makes you a pariah. It's a miracle he didn't kill himself at the end of the book.
- Mr. Forgetful being sad over his habit of losing his memory after he muddles up the message he was supposed to give to Farmer Fields. Mood Whiplash ensues however when he bumps into the sheep he was supposed to report missing and he finally remembers the message.
- The end of Mr. Clever's story. Where he walks back home to Cleverland, not feeling as clever as he once thought he was, then to rub salt in the wound, it turns out that he's walking in the wrong direction.
- The ending of Mr. Wrong is quite sad, in that he meets Mr. Right, who teaches him "right" ways, and Mr. Wrong becomes a "changed Mr. Man". But then:You might think that's the end of the story, but it isn't.The more right Mr. Wrong became, the more wrong Mr Right had become.Isn't that extraordinary?"Oh dear, my plan didn't work the way I'd hoped," said Mr. Right, and he went to bed.In the bath!
- It really is tragic how Mr. Rude (Much like with Mr. Uppity above) was Hated by All and he essentially squanders a chance to actually make a friend in Little Miss Tiny by insulting her and leaving her in tears despite her giving him a friendly greeting.
- Mr. Muddle does not reform, unlike many of the other "negative" Mr Men. Instead, everybody gaslights him into thinking that he's doing the right thing, by saying "Well done, Mr. Muddle" when he did the wrong thing. He is so pleased, that he cooks himself a special meal of roast turkey, peas, potatoes, and gravy, with the following result:He put the turkey in the cupboard to cook!He peeled the peas!He put the potatoes in the refrigerator to boil!And then, do you know what he did?He tried to slice the gravy!! Oh Mr. Muddle!
- "Little Miss Shy and the Fairy Godmother" has Little Miss Naughty and Little Miss Bossy mocking Little Miss Shy for blushing and making her cry. Even knowing that this is Little Miss Naughty and Little Miss Bossy we are talking about, it was still very cruel. It's supposed to be a parody of the scene in Cinderella where the stepsisters destroy her dress but it might not make it any less upsetting for some peoplenote .
- "Adventure With Monsters": While the monsters turn out to be friendly, it can still be rather distressing seeing the Mr. Men and Little Miss (Mr. Tickle especially) scared that they're about to die.
- The whole of Mr Tickle In A Tangle is pretty sad. First Mr. Tickle ends up having his one of his extraordinarily long arms get stuck in the banister when he tries to tickle the postman, then he has it get stepped on by the bus conductor when he tries to tickle the bus driver, ends up getting them tangled in the revolving door of a hotel where he was meant to meet up with Mr. Uppity for lunch and even though he's saved by the fire brigade, he ends up missing his lunch date with Uppity which leaves him very upset because it also means no tickles, he then has his arms get tied up by Little Miss Naughty when he tries to tickle her and goes home feeling miserable because of how much of a horrible day he'd had. fortunately, Little Miss Tiny comes over giving him a chance to tickle somebody before the day's out.
- The ending of Mr. Men: 12 Days Of Christmas. It's supposed to be Played for Laughs what with Mr. Wrong thinking that it's summer and going off on a holiday but think about it from Mr. Muddle's perspective, it was the one time he actually delivered a gift on December 25th after spending the whole year giving the wrong gifts to his friends on the wrong days and the person he delivered it to believes that Mr. Muddle got the date wrong meaning that his plan to get the right date was All for Nothing.
- Little Miss Inventor And The Robots: It's quite upsetting as well as horrifying to see the Bossybot forbey Mr. Funny from telling jokes, Little Miss Giggles from giggling and Little Miss Hug from hugging anybody as well as getting the Extendabot to tie up Mr. Tickle in knots. (Most likely so he wouldn't be able to tickle anyone anymore.)
- It's small compared to most moments, but Mr. Happy is left very upset and in pain after Mr. Grumpy steps on his foot just for suggesting he does not act too bad tempered.
Musical
- The reprise of Happy, what with it ending with Mr. Happy bursting into tears after having to put up with Mr. Grumpy's grumpiness for too long.
