Mr. Miserable is a yellow and sad Mr. Man. He eventually learns to smile a while after setting foot into Happyland. Some people claim he made a cameo in a thermometer in the Mr. Men episode, Sneezes and Hiccups.
- In the 1975 cartoon, he and Mr. Happy both bumped into each other while laughing and became one and then split apart.
- He is possibly a relative of Mr. Nobody
- Turner (Handy Manny, both are miserable),
- Strong Sad (Homestar Runner, both used to be sad and miserable)
- Weeper (A Snow White Christmas, both are sad and miserable)
- Boomer (TUGS, both were sad and miserable when they were first discovered)
- Mr. Nobody (his own series both were sad and miserable when they were first discovered by Mr Happy)
- Octo (Almost naked animals both are rounded, sad, and miserable)
- Neville (from Thomas & Friends, both are left out)
- Ezekiel (Total Drama World Tour both are all alone)
- Gordon (Thomas & Friends, both are miserable when in trouble)
- Eeyore (Winnie the Pooh, both are gloomy and miserable)
- Thomas Molison (The Black Balloon, both were left out)
- Horton the Elephant (Dr. Suess, both are miserable sometimes)
- Mutsumi Saburo (Sgt Frog, both are usually alone)
- Cubone (Pokemon, both are sad and miserable)
- Sad Sack (The Raggy Dolls, both are gloomy)
- Grizzle (Timbuctoo, both are miserable)
- Zor (The Deadly Six, Sonic Lost World, both are miserable)
- Sadness (Inside Out, both are down in the dumps)
- Godfrey the Horse (Fourways Farm, both are miserable)
- Crimson and Ennui (The Ridonculuos Race, all three are gloomy)
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