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- The South Korean mice in the propaganda-tastic North Korean series Squirrel and Hedgehog. The pair, consisting of domineering Jerkass Mulmangcho and his meeker, one-eared companion Yelipalip, migrate from faction to faction amongst the villains, and are consistently mistreated and abused. All of their efforts to prove their worth, do something evil, and make it higher up in the ranks of whichever group they're currently attached to inevitably fail, miserably and pitifully, usually thanks to the heroes. More than once, the two are actually arrested and imprisoned by their own bosses and almost executed because they got the blame for what the undercover good guys, Geumsagi and Juldarami, did. So far, they have always managed to somehow get out of such situations alive. Although they clearly want to be evil and respected (Mulmangcho more so than Yelipalip), they fail so often and so pitifully it's difficult not to feel bad for them.
It should also be noted that this was originally an evil trio of Ineffectual Sympathetic Villains, but the third guy, Mulsajo, whose distinguishing characteristic was that he wore a pink shirt, was even more ineffectual than his comrades and was blown up with a grenade midway through one of the earlier story arcs, leaving just his two buddies to carry the mantle of constantly failing.
- Most of the so-called "villains" of The Prayer Warriors count, but Grover stands out in "The Evil Gods Part 1". He typically can't do more than threaten or taunt the "heroes", and while it's implied that he played a role in Chiron's off-screen death after converting and returning to Camp Half-Blood to convert the others, in the resulting fight with Percy, he gets defeated and beheaded fairly quickly.
- The Metarex of Sonic X: Dark Chaos become this trope thanks to flanderization and Villain Decay. This is notably averted with Eggman, who has taken several levels in badass.
- Dr. Einstein of Arsenic and Old Lace. At the very least, he's helped Jonathan escape from jail and evade the police. He probably has something to do with the latter's ability to be a contender in the play's Body-Count Competition as well. However, he's clearly motivated by fear and spends a lot of time drunk. This may be the reason for his escape at the end.
- In Ruddigore, when the protagonist Robin becomes Sir Ruthven Murgatroyd, he finds that he can't commit evil deeds if his life depended on it, which is exactly the predicament he's in.
- Virgil, the Million Dollar Man A.K.A Ted Dibiase's dragon was presented this way during his WWE wrestling career. For years Ted Dibiase treated Virgil like a servant, yet Virgil would do whatever Heel action he was told. That is until a storyline was created where Virgil turned against Ted Dibiase and became a Face.
- Ariana was this in LLF during 2004, where she was so ineffectual that even when they were on the verge of winning a match she screwed so much up that her Tag Team partner Princesa Sugey snapped and assaulted her, then Polly Star, who was recovering from a prior match, decided join in. Ariana was so sympathetic that rather than try to win the match on of her tecnica opponents tried to protect her and adding to whole thing was the referee ruling the disqualification in favor of the tecnicas, so they won anyway.
- Particularly worth mentioning is Simon Dean, the heel version of fitness freak Richard Simmons in WWE in the mid-2000s. He never won a match against a non-jobber. (Of course, Dean wasn't really evil so much as he was very, very annoying, which is enough to make you a heel in WWE.)
- AJ Styles during the Angle Alliance Christian Coalition feud in TNA, him essentially serving as the fall guy of both groups.
- Montel Vontavious Porter on Smackdown after he lost the United States Championship and continued to lose every match he had afterwards, to the point Theodore Long refused to pay him the bonuses that were in his contract and took away MVP's NFL style inflatable tunnel entrance. Fans began to cheer for him out of sympathy.
- Hydra in Chikara, mostly due to the fact he was only 130 lbs, making it really easy to sympathize with him against almost everyone he was matched up with.
- Layla El during the Laycool period. While they were both rotten people, Layla was also goofy, small and tended to take the losing pin or submission hold when the team lost. And Layla also seemed to genuinely care about Michelle McCool, who was growing increasingly tired of her.
- Jakob Hammermeier, to give Chikara another entry on this page, in that he has an abusive Bad Boss in Tim Donst. When Donst is not around however, this trope is not in play either.
- Despite spending at least half of her career as part of the hostile occupying Power Stable Oedo tai and being as willing to commit fouls as most other members, Kris Wolf serves as such in World Wonder Ring STARDOM simply because she's so happy and energetic that she doesn't come off as being very malicious and she remains in good spirits facing many setbacks. Being pretty tiny helps too. Even the other goofy members such as Kyoko Kimura, for one contrast, tend to have worrying tempers, sadistic streaks, devious plots and success in their endeavors, which means they don't get showered in as many cheers or streamers.