The entirety of the Gedou Otome Tai from Akahori Gedou Hour Rabuge. While they're daughters of low-ranking mooks from an evil organization, their ability to actually do anything evil is zero. And those that actually DO gets turned around very quickly.
Shia in Pita-ten is the epitome of this trope; as demon she's not only supposed to do evil, she *has* to do evil, but she always seems to wind up baking cookies for everybody, or cleaning up the apartment she shares with Misha (an angel almost as bad at doing good as she is at doing evil), or just in general being polite, soft-spoken and helpful, much to the exasperation of her demon-adviser in cat form, Nyaa.
In the manga When she dies Nyaa admits that she may have been a far more successful demon than he realized by making everyone love her then dying and leaving everyone sad.
DojiDevil, a one-shot character in the Hot Springs Episode of Kyouran Kazoku Nikki, always on cleaning duty as punishment. She was trying to find whoever was fated to die at the springs (it ended up being a Self-Fulfilling Prophecy) so she could steal a soul and gain recognition, but was so touched by them that she spent most of her time cheering them on and trying to help them. She finally sets up a plan to kill them all so the family won't be separated but regrets this almost immediately.
Shiyu Kusanagi in the X/1999 manga, CD Drama and TV series. What is a Gentle Giant who goes out of his way to help other people (including his enemies!) doing in the humanity-destroying Dragons of the Earth group?
Demon God Ifurita in the TV series version of El-Hazard
Chachamaru on Mahou Sensei Negima! is technically a villain because she's trying to kill Negi, but that's only because she's following her programming. When she's not doing that, she can be seen retrieving lost balloons for little girls, helping old ladies across the street, and rescuing stray cats.
In Ratman, the minions of Jackal, who wear spooky skeleton outfits, in the first chapter forget they were supposed to kidnap Shuto. So they instead played with and fed stray kittens.
Antylamon, the last of the 12 Devas in Digimon Tamers. While the other Devas would usually attack humans on sight, Antylamon doesn't attack or threaten Suzie, the first human she meets, at all. Suzie even makes her do a Heel Face Turn, as she not only defends Suzie from Makuramon, but becomes her partner.
Android 16, in Dragon Ball Z. He was created for the sole purpose of destroying Goku, and refuses to fight anyone but him. He also takes an interest in birds and squirrels, and loves the world so much that the only character in the series he does try to kill is Cell.
Hopper's brother Molt in A Bugs Life. While Hopper is malicious, cunning and depraved, Molt is... not.
Hopper:(to Molt) I swear, if I hadn't promised mother, on her death-bed that I wouldn't kill you, I would kill you!
Jenner's best friend and minion Sullivan from The Secret Of NIMH isn't really a bad guy at all, he just didn't choose his friends wisely. When Jenner plots to kill Nicodemus and Mrs. Brisby's children he objects to this, which leads to his Heel Face Turn. Unfortunately, before he can officially join the heroes, he is stabbed in the back and mortally wounded by Jenner for interfering with his plans... but before he expires he pulls a Redemption Equals Death when he throws a dagger into Jenner's back and kills him... with his last dying breath.
Tiger from An American Tail makes his appearence as a member of the Mott Street Maulers, a gang of cats that Fievel runs into. However, he quickly proves to be a goofy lug of a cat(A vegetarian, for one) and Not So Different from Fievel himself. After the big musical number that allows Fievel to escape from his cage Tiger is quickly fired but doesn't mind, and when all is said and done helps Fievel's family with the search.
Kronk from The Emperor's New Groove doesn't quite get the villainy thing. Not so useful, since he's Yzma's only henchman.
Bartok in Anastasia. He's not particularely evil for serving such a dark master, and not very competent either; he almost kills Rasputin when he tries to break his phylactery on a whim.
Films — Live-Action
In Mean Girls, Karen seems to be remarkably lacking in actual meanness per se; in nearly all respects she comes across as a good natured ditz. In fact, her only real defining characteristic, besides being The Ditz, is that she remains a loyal friend to Gretchen even through Gretchen's Villainous Breakdown.
Gretchen isn't all that malicious either, just desperately insecure and hungry for attention, which makes her extremely prone to gossip and over dramatize things ("Pusher? Like a drug pusher?"). Makes more sense if you consider that in the original script she was described as ugly.
From Tombstone: Sherman Mc Masters, Texas Jack Vermillion, and Turkey Creek Jack Johnson don't mind robbin' and stealin', but don't like messin' with the women for the evulz. Also Deputy Billy Breckinridge thinks there has to be some law.
From The Sorcerer's Apprentice: Drake Stone, an arrogant Morganian turned celebrity illusionist, is recruited by Horvath to release Morgana, but he never does anything that evil. It's pretty clear that Drake starts to feel incredibly uncomfortable with the consequences of his actions, especially when Horvath implies that children will die for his cause.
Evil's assistants in Time Bandits are all pretty dim and full of useless suggestions.
Paul Dooley's incompetent and inarticulate Claude Elsinore in Strange Brew
Smee, Captain Hook's bosun in Peter Pan, as well as its many adaptations.
The Mistmantle Chronicles has this in the form of the female squirrels Crackle and Gleaner. To quote, "Crackle seemed to go out of her way to make trouble, while Gleaner seemed to do it naturally." Crackle quickly becomes part of the supporting cast and one of their friends after she comes to work at the tower as a cook, also partially upset that Gleaner has forgotten about her while serving the Big Bad's wife, Lady Aspen.
The children's book Which Witch? features Belladonna, who tries her hardest to be an evil, hag-faced black witch like all the rest. Unfortunately her natural tendency is that of a Purity Sue-level white witch that makes all the other witches feel sick.
There was also Malakili, the Rancor Keeper (seen briefly in the movie after Luke was forced to kill the beast) who was a close friend of Porcellus, coincidentally. Malakili befriended the Rancor, and was the only person it wouldn't attack. He pleaded with his boss to give it a better diet, but Jabba insisted on keeping it hungry so it would be more ferocious when he needed to execute a prisoner. When Luke killed the creature, Malakili blamed Jabba for it, having known that if his warnings had been heeded, it might not have happened.
Another Star Wars example was Atour Riten, an Imperial Officer serving on the first Death Star (Who is featured prominently in the novel Death Star.) He saw the destruction of Alderan as beyond cruel, and silently swore to devote his life to fighting his employers. He later helped Luke Skywalker and Han Solo rescue Leia by lowering the security systems on her cell block, although he doubted they would succeed. (As he told them himself, "Good luck, you'll need it.") He later aided a team of other defectors in escaping the Death Star during the Battle of Yavin. And ultimately, to ensure that they would escape, he forfeited his chance to do so himself, dying when the Death Star was destroyed as a result.
In fact, the whole novel is full of guys like this.
Played for Drama with Draco Malfoy from Harry Potter. For the first five books, he was a Jerkass who never got closer than Red Herring to being a real villain. When he was finally given an important job by the bad guys in Half-Blood Prince, it quickly became clear that he couldn't do real evil; he tried to kill Dumbledore indirectly but all of his attempts failed. When he finally had a golden opportunity to kill him on the spot, he couldn't go through with it, and only disarmed him. The only reason he tried to go through with it was fear of what Voldemort would do to him and his family. Oh, and Dumbledore was perfectly aware of what he was up to the whole time, but didn't approach him for fear of Voldemort catching on through Legilemency. Also in Deathly Hallows, when the trio are caught and brought to Malfoy Manor, and Draco is asked to take a look at them to see if they've got the real Harry Potter, he clearly knows it's them, and is clearly reluctant to identify them, since he knows that doing so will ensure that Voldemort will come and kill them.
A variation of this theme occurs in the satire The Screwtape Letters, with the apprentice devil Wormwood. He wants to be an evil tempter of mortals, but he's really bad at it. He keeps making mistakes, getting both him and his uncle (the veteran tempter Screwtape) in trouble, and failing miserably in the end.
Live Action TV
Doctor Who has plenty of examples, most recently Luke Rattigan in The Poison Sky, who thinks the Sontarans killing people with his inventions is cool but lacks the nerve to get his own hands dirty and ultimately sacrifices himself so the Doctor won't have to.
Davey in the pilot of The Sarah Jane Adventures. This is the guy who refuses to follow Maria and Luke into a womens' bathroom, because "That room is designated for females only. We are males... this culture says we must never go in."
Well, if you overlook the "murdering a girl in cold blood" thing or the fact he seems to hate Bajorans even more than his boss... He's actually more of a Dragon Ascendant who does a Heel Face Turn.
Garry and Grahame in Maid Marian and Her Merry Men. They're inept to the point Marian and co quite like them when they're not pursuing them on Nottingham's orders.
The guards in Robin Hood, meanwhile, turn out to have a C- In Evil. They won't obey orders to strike down unarmed peasants during a sit-in, but as soon as it turns into a proper fight they're right back in the game, even though it's still mostly a proper fight with unarmed peasants.
Sgt. Schultz from Hogan's Heroes is often seen a a bumbling underling to Colonel Klink, and unlike most of Those Wacky Nazis, he is willing to turn a blind eye to Hogan and his crew's antics. In his backstory, he made toys for children.
Joxer's first appearance had him working for the villain Callisto. Gabrielle pointed out that he just wasn't cut out for evil. He later pulled a Heel Face Turn, becoming an earnest (and somewhat less incompetent) hero.
Ares' bumbling sidekick Strife, despite being a god, was a similarly incompetent character who never really caused trouble or meant anyone harm, and was constantly bullied and insulted by Ares for it. Ares did mourn for Strife, though, after Callisto killed him with a god-slaying weapon...
Ares (visibly shaken): He wasn't so bad. He tried hard. He... he was just no good at his job.
Buffy: Harmony, when you tried to be head cheerleader, you were bad. When you tried to chair the homecoming committee, you were really bad. But when you try to be bad? You suck.
Rusty the Tow Truck in the preschool series The Big Garage. In fact, in every single episode, he always joins the cast for the final song of the episode, and leaves the garage just before the credits roll.
My Name Is Earl: Despite Joy's best efforts, Darnell is too much of a Nice Guy to shore up the household budget with petty theft like Earl used to. He tries to snatch a little old lady's purse and run away, but he barely makes it ten steps before he starts feeling guilty and goes back to return it and apologise. She is so charmed by his guilty-puppy-dog look that she offers him a candy bar. Even when Joy is plotting against or yelling at Earl, Darnell and Earl always exchange a friendly hello.
Mystery Science Theater 3000: The sidekicks of Dr Forrester (TV's Frank) and Pearl (Professor Bobo and Brain Guy) are just silly lackies who are browbeaten into servitude.
In Power Rangers In Space, there was Waspicable, a bee-like Monster of the Week working for Astronema who could not be evil no matter how much he tried. He was a depressed creature, who thought that his reluctance to do evil made him a bad monster. When he had Cassie dead to rights, aiming a laser gun at her point-blank, he instead chose to shoot a Quantron behind her. Cassie actually felt bad later about hurting his feelings. His ultimate fate is unknown, but more than likely, his kind heart spared him from being destroyed by Zordon's energy wave in "Countdown To Destruction".
In the 1985 TV movie Family Ties Vacation, the Keaton family goes to England and unknowingly gets possession of important microfilm sought by a sinister foreign spy. The spy's less sinister henchman helps out the Keatons in the end because they're "such nice people".
Many of the German soldiers in the Britcom'Allo 'Allo!, but especially kindhearted Lt. Hubert Gruber, as typified by his disastrous attempts at interrogation.
Played straight on Roots. A poor white man is hoping to be hired as an overseer on a slave plantation. A couple of the slaves teach him how to sound and act right for the role. (They find it hilarious when he actually says "please" to a slave.) Their reasoning is, an overseer who has to remember to be brutal is much better than one who does it naturally.
Scumspawn in the BBC Radio 4 comedy series Old Harry's Game. He is a demon, one of Satan's chief minions, and much is made of his disgusting physical appearance. He also donates to donkey sanctuaries, is a supporter of Friends of the Earth, is often exceedingly kind to the damned, and has a chaste but touching love for his master.
When Harry Biscuit becomes Mr Gently Benevolent's evil minion in Bleak Expectations, he does things like insult someone's tie. When Pippa Bin follows him to the dark side, Mr Benevolent has to keep explaining that "bad" might be a synonym for "evil", but there is a difference between doing something evilly, and doing it badly.
Washing up badly is not the same as washing up evilly, it is merely unhygienic. Washing up evilly involves crying children, smashed plates and at least two dead dogs.
In Damn Yankees, Lola fails miserably at playing The Vamp when it comes to Joe. Nothing disgusts Applegate more than having her sympathize with the man she is supposed to seduce.
Although it's implied that she is usually far more effective. Her first few lines involve her mentioning very off-handedly that she drove a man to suicide and asking quite eagerly if she should make the next one jump off the Empire State building. She even has a song devoted to several past, successful exploits. Lola only took to Joe because he was the only guy faithful enough to his wife to not succumb to her seduction.
Sir Ruthven Murgatroyd (alias Robin Oakapple) from Gilbert and Sullivan's Ruddigore. Despite hiding from his inheritance of the title of Bad Baronet of Ruddigore (and the related curse that would force him to commit a crime a day or perish in terrible agony), he is discovered and pushed into the role. The problem is, he's not really very good at committing crimes and many of his attempts end up being more rude than fiendish. When the disgusted ghosts of previous Bad Barons exhort him to at least carry off a lady or something, he protests that he "isn't that kind of Bad Baron!" They have to give him a taste of the terrible agony to prod him into it.
In fandom, Demyx, the magical sitar player of Organization XIII is either an example of this trope or an incredibly scary and evil Crouching Moron, Hidden Badass. In the game itself, he carries cue cards with his mission on them, and his first line is "Run! Run away!"
358/2 Days expands on this. He now bribes Roxas to do his missions for him and chats gleefully about how being lazy saved him from getting killed at Oblivion.
Johnny Sasaki in Metal Gear Solid 2 and his identically named and voiced grandfather in Metal Gear Solid 3. While just incompetent in 1, he progressed to the point of making friendly conversation with the people he's on patrol for in 2, and his grandfather even shows family pictures to the people he's guarding. Oddly enough, becomes a major character and Took a Level in Badass in 4.
The Koopa Kids from the Mario Party games do this from time to time. One would take coins from players, but occasionally would give coins instead, then realize his mistake and leave anyway.
Balrog from Cave Story is only a villain because the Demon Crown compels him to obey the Big Bad. When nobody's looking, he's cheerful, helpful and saves Quote and Curly Brace from the Load BearingBonus Boss Ballos.
In the final case of the Phoenix Wright trilogy of the Ace Attorney series, there is a character who receives instructions to help with a murder and is so innocent as to misinterpret them as instructions to throw gravy onto a portrait. The same case also involves a Purity Sue who is absolutely committed to helping protect both a Complete Monster and a Sympathetic Murderer and following any instructions from them regarding how to help them avoid being caught.
Bianca of Spyro the Dragon spends most of her first appearance acting as the Sorceress'meek and clumsy underling, badly attempting to intimidate Spyro out of taking back their stolen colony of dragon eggs (which gradually breaks down into her practically begging him to go back so he spares himself her abusive master's wrath). She eventually pulls a Heel Face Turn after finding our the Sorceress' plans for the eggs were far less well intentioned than she expected (as well as gaining a crush on Spyro's ally, Hunter).
The Monster in the Darkness, who manages to spend most of an epic battle scene having a tea party, and constantly fails to grasp the main plan of the villains. He even gets a Crowning Moment of Heartwarming with a captured paladin which causes one to wonder if he's even trying to be evil. It's made clear that he should be incredibly dangerous, on account of his massive strength and durability, along with vague but powerful other abilities, but his personality renders him (in the words of Redcloak) "about as scary as musty styrofoam." He later saves said paladin (named O-chul) and Vaarsuvius from death via ingested meteors. He teleports them away and Xykon doesn't even realize it was The Monster in the Darkness who did it.
Thog from the Linear Guild has elements of this as well. Though he's actually very good at killing people, he's too .asinine to realize that this is bad and would be equally content eating ice cream or playing with a puppy (or whatever poor bystander he can force into the role of the puppy). He can be rather cruel though, even if he does it in an "innocent" way.
Lampshaded by the imp Quarr when Therkla saves the heroes because she has a crush on Elan.
Quarr: No wonder you people need us to tell you how to be Evil, you'd just screw it up on your own.
8-Bit Theater features so many subversions of standard hero and villain roles that this trope inevitably shows up, most notably with Garland, who can't seem to grasp that offering the goodguys cupcakes is not proper behavior for a wannabe Evil Overlord. It's so bad that his captive, Princess Sara, has to help him be evil. The rest of the Dark Warriors are hardly any better: Bikke makes Ralph Wiggum look bright (his worst "crime" is getting his entire crew killed by being too cheap to feed them), Vilbert is a Goth vampire who thinks he's in a LARP, and Drizz'l might be a threat except that he's forced to play Only Sane Man for the other three idiots.
This is also inverted, as the most effective villains in the entire story, by atrocities committed, are the Light Warriors, of whom Fighter is the only actually good member (maybe). He fails to be evil so thoroughly that he genuinely believes that he and his murderous, sociopathic friends are the good guys.
The Light Warriors fall into this a lot—not because they're not evil enough, but because they're too .asinine to do it right.
During the "That Which Redeems" story arc from Sluggy Freelance, the Dimension of Pain demons start turning people in the Dimension of Lame into demons as well. However, as one demon puts it, "When you start with wussie mortals you get wussie demons."
Much later on, a journey to the Earth's surface to rescue Gloog from the main characters instead results in him being forced into helping and then being beaten senseless by a senile old woman.
Jurinjo from Emergency Exit is amazing at this trope. He helps Eddie buy groceries, delays reporting back from a mission until he eats ice cream and sees a dancing monkey, shows the heroes the location of a Plot Coupon, has doubts about continuing to work for the villain, doesn't want to attack an opponent who seems to be less well armed then he is, is upset when another villain attacks one of the heroes , offers to heal the hero and has to be reminded that villains usually asks for payment, and actually holds up his end of the deal and seems to be making friends with one of the heroes.
To a lesser degree, Orulla.
Dr. Kinesis' minions in Evil Plan, who seem to think that Kinesis' cruelty is simply the way their leader shows them he loves them. Hint: It isn't.
Fuchsia from Sinfest gradually became this after crushing on Criminy. Now, instead of tormenting the souls of the damned, she reads them stories and sings comforting songs to them.
The green devil girl brought in to replace Fuschia after she bailed on Satan is a perky, kindhearted Cute Clumsy Girl who is bothered by the torture and screaming of the eternally damned. She works for Satan, but doesn't seem to have a clue what the mission statement is.
Wilson and especially Pickett, Notfunny Cartoons' resident mad scientists. Examples include the Killbot 5000, who works as a kindergartener because he couldn't bring himself to hurt a soul, or the genetically engineered werewolves, which would be fine if they didn't keep on coddling rather than killing. At one point, Wilson accuses Pickett of not being serious about this whole "evil science" thing. Pickett quickly pulls out a remote with a big red button, saying he's not sure anymore what it does, but if he recalls correctly, it should be something very bad. So Wilson presses it. A split second later, the phone rings. When they pick it up, the response is "Something very good just happened. Thank you."
Evil Diva: The title character. Even when the school sends home a letter to alert her parents to how good she is acting, she can't help herself but help a kitten caught in a tree.
Richard from Looking for Group got hauled in front of a court of his (evil) peers because he'd become a minion to protagonist Cale. Eventually he got bored and, shall we say, opted out of the proceedings.
Inferno of APT Comic. A henchmen of Eggman, and loyal unlike, say, Shadow. But he's not exactly doing anything worse than making pouty faces.
He does try though: after being sent on a mission by John with the uberbunny and WV, he gets the idea to steal the wallet John gave WV. He then escapes and contacts his superior, Jack Noir. Unfortunately for him, that wasn't his mission in the first place, so he gets barked at. He then goes and actually does his mission, which was to kill Jade. Because of Jack Noir's feelings for Jade he inherited from Becquerel, he kills the Droll and sets up Jade's resurrection. Poor Courtyard Droll.
Red vs. Blue: Played with in an odd way. Caboose has to pretend to be evil in order to be useful in a fight. He does this by imagining kittens with spikes on them, and declaring a hatred for babies. Nonetheless, he utterly destroys the mooks he was fighting.
In the League of Super Evil, Red Menace's tendency in this direction gets so noticeable that the others outfit him with a Pavlovian reward-punishment hat.
The Grubs are too dim to be properly evil-when quizzed on what they hate most about Buzz, they say, "I donno. He seems like a pretty nice guy." The Brain Pods are better at it (since their purpose is to be smart) but the thinking aspect is all they're good for.
Stormer on Jem; a few episodes even dealt with the fact.
The best known being the one where she and Kimber form their own duo group; Stormer only returns to the Misfits because she cares too much to let her friends utterly fail, which they would without her.
Hack and Slash from ReBoot, who are dismayed when Bob is lost in the Web and unable to keep them from doing anything really bad, like killing others. Though, considering their level of competence following their Heel Face Turn, they also have an F in Good as well.
Guild henchmen from The Venture Brothers (except for the Guild Blackout squad sent to assassinate the Venture family under orders from Phantom Limb) In fact, the typical henchman is more along the lines of a Punch Clock Villain than a true servant of evil. Guild henchmen are portrayed as ordinary civilians who just chose an atypical line of work, and thus most of them can't really comprehend their boss' schemes. They can and are used as deadly tools of the supervillain's mastery, but are more typically comfortable with engineering or secretarial positions, or just tag along with the supervillain as he or she live their own lives.
Numbers 21 and 24, employed by the Monarch, especially fail at evil. If they took an evil test, they would not likely get more than a 10%. They are generally useless in combat, have little strategic ability, and they spend their time bickering over fantasy fistfights instead of actually participating in villainy. Their Genre Savvy ability is beyond compare though, making them in the words of the Monarch, "That special mix of expendable and invulnerable", which is how they survive for so long; they know being evil/loyal is the fastest way to die by Brock's hands.
21 subverted this in season 4 after witnessing 24's murder/accidental death when he Took a Level in Badass by completely whipping his body and selfdiscipline into shape and becoming "General 21", a highly trained, merciless supersoldier. However he still does not fare very well in the evil department, as he completely fails to torture Hank and Dean and openly admits to them that he cannot tap into his inner hatred the way the Monarch can.
Their own boss The Monarch has his own incompetent moments as well. When discussing his arching plans with Monstroso, he suggests "coating the Venture compound with honey so he's devoured by ants and jiggers" and then "stick him in a bag and beat him with a rake." Monstroso shoots down both plans as being .asinine.
GIR from Invader Zim. The one time he became a competent villain he nearly killed Zim.
In Codename Kids Next Door, the pirate Stickybeard had a hechman named Dumb John Silver. (Give you one guess how he got that name.) Of course, maybe he wasn't too dumb... He was smart enough to quit after Stickybeard insulted him for not being evil enough.
Mr. Sunshine, [[.asinineBoss Rancid Rabbit]]'s assistant from CatDog.
This is arguably inherent in the word "minion" itself—its etymology is from the French mignon, meaning "cute." The connection comes from the Camp Gay French King Henri III having a fondness for Pretty Boy courtiers for various kinds of liaisons, diplomatic and romantic alike.
Erwin Rommel. Yes, him, the original Magnificent Bastard. He wasn't remotely interested in Hitler's idea of a master race and did know about the plan to overthrow Hitler in the 20 July Plot without interfering. He was forced to commit suicide to protect his staff and family.
Karl Dönitz, according to this Cracked.com article. Brutally efficient at his job as submarine captain and Admiral in Chief, he had still shown mercy by giving supplies to the surviving crews of the ships that he had sunk. Those Pet the Dog moments saved his life during Nuremberg Trials and he is one of the few members of Nazi high command that got a prison sentence instead of death penalty.
Likewise, during his brief tenure as Reichspräsident in the wake of Hitler's suicide, Dönitz earned points with the Allies by attempting to ensure all loyal German troops surrendered to the British and American forces, (but not the Soviets), in the hopes that Germany could negotiate a peace treaty. This ultimately saved over 1.8 million lives.
Yet he was still an unrepentant racist, antisemite and die-hard Yes Man of Hitler. He was to the Navy what Keitel was to the Army, only slightly more competent.