Dante: I'm not really interested in mending fences with my brother, so here's my counteroffer: You give me a job that can pay my electric bill for the year, and I'll leave you here with your head attached to your body.
Mephisto: ...Actually, there's a fiend called Blackheart who has caused me trouble to no end.
Dante: Done. But I'm charging you triple because you're such a tool.
Some stories portray the devil as a weak and ineffectual (if unrelentingly evil) guy. He may be more worried about getting his Wood Elf character to level 70 or catching the latest episode of Avatar and the Airbending Fellowship of Vampire Slayers than punishing the damned or tempting mortals, or perhaps he's unattractive and lives in God's basement. Perhaps he gets outsmarted every time he tries to make a deal with a mortal. Maybe he's plagued by Daddy Issues (being the original rebel and all).
Naturally, he's no match at all for the forces of heaven. Jesus doesn't need to know kung fu to humiliate him and is in any case much cooler than him. His former fellows among the angels can give him wedgies at will. A Good Shepherd can talk him into submission. Heck, even a mortal guy with a cross could drive him back.
Some works will use Evil Is Petty to show this. It's pretty hard to think the devil is cool when he spends most of his time writing rude words in the public toilet and prank-calling the church.
Its most common in medieval and more traditional Christian portrayals to show him as a thug, dangerous but also easy to fool and really only waiting for someone stupid enough to sin. If he's intelligent, its only something he puts on when its convenient and discards at the first possibility, since his hatred for God extends to hatred for the wisdom He provides. The Inverted Trope to this, where Satan is a stylish, seductive badass, is a modern invention largely derived from Doctor Faustus.
If the Devil's job sucks enough then he may decide to leave it to someone else altogether; see To Hell with This Infernal Job. If the Devil sucks at his job enough then someone else might take it from him; see Hell Has New Management.
For other non-threatening spirits that personify death, see Don't Fear the Reaper.
- In this commercial for Halo Top Ice Cream, the Devil is upset because the product is delicious but can be eaten guilt-free, complaining to the guy at the Pearly Gates that ice cream is supposed to make you feel ashamed. Of course, he loves it too much not to eat it himself.) The storyline continues in later commercials, where he tries to sue the angel with a team of damned lawyers, failing again because they can't stop eating it either, and later a third where he offers to stop making Segways if the angel stops making the ice cream.
- In The Devil Is a Part-Timer!, the Demon King and The Dragon flee the hero Emilia Justina by jumping through a portal to Earth. Upon arrival, the lack of ambient magic makes them lose their powers. Guess who ends up working at MgRonalds?
- Downplayed by the fact that he enjoys his job, takes his fall from power remarkably well, and is a charismatic Nice Guy. He's also not the biblical devil; Satan is a very common name among demons.
- There's also the fact that he was in a similar situation back in his world when we has younger. At the very bottom of the pecking order, Satan had his life saved by Emi's mother, an angel, and while recuperating, was tutored by her in various subjects. He proceeded to use his newfound knowledge to slowly rise through the ranks and eventually become the King of the Demons. Who's to say he can't the same on Earth? The guy is patient.
- In Puella Magi Madoka Magica the Movie: Rebellion, Homura becomes a self-admitted demon who hates the world and (almost) everyone in it. But, for all her power, she isn't happy. Fundamentally, she is still the same alienated, self-hating pessimist we met in the first episode. Even her servants pelt her with tomatoes.
- Gabriel Dropout has Satanichia who is a petty Harmless Villain who fails spectacularly at being evil. Her ideas of heinous acts include recycling a bottle with the cap still on, not refilling the toilet paper dispenser, and deliberately not doing her homework.
- Neron, DC Comics's version of the Devil, fits often:
- In Underworld Unleashed, Neron loses because Captain Marvel's soul is too pure. He then loses his throne in the Reign in Hell comics.
- Neron struck out in a way similar to the way Mephisto succeeded in One More Day below. After many of The Flash's old villains Came Back Wrong (Neron himself was responsible) Wally and his wife Linda made separate deals with Neron to set them right (since they were mindless killing machines far more evil and dangerous than they used to be). Except instead of their souls, Neron asked each to give up their love for the other. Both agreed, and they split. (Un)fortunately, holding their love 'polluted' Neron, and he became nice, something which was Hell to him. He asked them to take back the bargain, and both refused (since neither one cared about the other, neither had any desire to get their love back). Ultimately the Neron begged them to take a new deal, taking back their love in return for him releasing any and all remaining hold on the villains.
- In another story, Neron offered Oracle her legs back; he didn't want her soul in return, he just wanted her to be his historian and write down his actions. Oracle actually considered it for a while, but eventually refused, saying it was selling her soul either way. He dropped the issue and just left.
- Satanus joins Neron as a loser by losing his throne to Blaze.
- Lucifer in the eponymous comic Lucifer has an Alternate Character Interpretation as a complete tool who really has no point other than to be spiteful to his old man. For all his accomplishments, cunning, and power he is a slave to his pride which allows him to be manipulated by God, trapped in Hell for eons because he could not admit to himself God tricked him into voluntarily taking ownership, and finally exiles himself from everyone and everything including the few who care about him (and vice-versa) because he cannot stand to be dependent on anyone and resents God for creating him in the first place because he is dependent on God for even existing.
- Even worse is that by the middle of the series he is fully aware that God designed him that way, he was always meant to be the rebellious one in order to keep the rest of the angels on their toes. Even then he is one of the only two archangels powerful enough to take God's throne when he vacates it (the other, Michael, doesn't take it largely because he doesn't feel worthy himself) but turns it down as he sees it as another form of trap to keep him from having true freedom.
- Mephisto has his ups and downs.
- He was enslaved to Thanos during The Infinity Gauntlet saga. He was once humiliated by the Black Panther by being cut off from his power and the crap beat out of him. He was Out-Gambitted by Doctor Doom, and even bested by his own son, Damien Hellstorm. Then in Thunderbolts he gets completely played and humiliated by the Leader Deadpool of all people. The Leader even taunts him when Mephisto threatens him, claiming that while Mephisto might be more evil than him, he's definitely smarter.
- In One More Day he dissolved the marriage of Spider-Man and Mary Jane. He once faked defeat against the Incredible Hulk to get him to become overconfident and destroy his own life later. He generally tends to fare better against other villains where he is allowed to win by outsmarting and humiliating them such as Black Heart, Hela, and Loki.
- Hellblazer: The First of The Fallen will NEVER succeed against John Constantine. It gets so bad that Constantine claims at one point if he is sent to Hell he can easily take over and the First is reduced to taunting Constantine from a distance with other demons being far more effective than him in hurting Constantine.
- The fallen angel Lucifer finally showed up in Ghost Rider after decades. Unlike other hell-lords like Mephisto and Satannish, he cannot leave Hell under his own power and had to trick Blaze into taking him with him. Despite claiming to be a master manipulator he is vulgar, crass and worse of all constantly tricked by Johnny Blaze, who both Blaze and Lucifer agree is something of an idiot, until finally being tricked into fighting Ghost Rider at half power, losing, and being sent back to Hell.
- This is the premise of The Lord of the Rings Mary Sue Hunters story The Game of the Gods. In it, Morgoth attempts to derail the books by inserting various Mary Sues in it, but ends up getting them killed through a loose grasp of the lore, the cleverness of his opponents, and sheer lack of common sense. By the end of the story, he's become rather pitiable.
- RainbowDoubleDash's Lunaverse: Tirek is, aside from Discord, the most terrifying and dangerous villain in the setting. His power at its height was equal to Celestia, and the mere thought of him potentially escaping his prison panics Luna enough that she decides it's a better option to obliterate the island he'd escape onto, even though the Element Bearers are on it, rather than risk him getting out. And he's been so utterly broken by what Luna did to him a thousand years ago, he's a broken shell of his former self, utterly afraid of leaving Tartarus. Not that he's got a problem with it.
Grogar: You have become nothing more than a wretched, pathetic coward.Tirek: The cowards survive.
- Bedazzled (1967) contains possibly the most literal example ever, in which Satan loses a wager with God and is sent to a Villainous Breakdown.
- In the Bedazzled (2000) remake the Devil (a beautiful woman) grants wishes to a man in exchange for his soul, but each wish results in a humiliating failure. It turns out that the Devil is actually harmless, since God owns all people's souls; they can't be sold! She's just a practical joker.
- The Haunted World of El Superbeasto: Dr. Satan is not Satan himself but some nerdy guy styled after him. In other words, "the guy pretending to be the devil is a loser".
- Zigzagged in Tenacious D in The Pick of Destiny. Old Scratch wins the rock off here against the two protagonists (and his performance here is wicked awesome, hammed up by Nirvana drummer Dave Grohl, who portrays him) but hes Out-Gambitted in the end and banished back to Hell by the duo anyway.
- In the Brazilian movie O Auto Da Compadecida, the Devil appears as an Amoral Attorney trying to damn the main characters after their deaths. While he is depicted as a very sinister figure whom everyone else is scared shitless of, The Hero makes fun of him all the time because he stinks of sulphur. The Devil also avoids looking at Jesus (who serves as the trial's judge) because his power is too holy for him to withstand and attempts to take his form in a pathetic attempt to emulate him. This trait is more pronounced in the original play, where he dresses himself in all white to pass himself as God.
- In The Divine Comedy, Satan is a towering imbecile, trapped chest-deep in ice and forever crying and beating his wings in a vain attempt to escape, which only cools and hardens the tears into ice, trapping him.
- The Brothers Karamazov: The devil takes the form of an emaciated, impoverished down-on-his-luck country gentleman. He also seems pretty resigned to be being blamed for all of mankind's ills. Not suave or sophisticated at all, but still capable of causing the occasional Heroic BSoD. He claims to take this form to mess with Ivan's sense of self-importance, but we all know that this just to help his own self-importance.
- A rare instance where this is not played for laughs: in C. S. Lewis' Perelandra, the Devil is perfectly capable of feats of supreme intelligence, strength, and many other virtues — which is precisely the trouble; he doesn't really like to use them, because they're good things. He's a petty, spiteful bastard who'll just as soon kill frogs or rip up chunks of turf for the pleasure of killing something as corrupt as an entire world.
- Lucifer is a loser in Wendy Alec's Brothers Series. After he corrupts Adam and Eve, he gains control of the race of men and its solar system, only to lose every battle or encounter he engages in after that. No matter what he does, God punishes him by reducing his power and authority, like a kid who was caught when his hand in a cookie jar.
- C. S. Lewis creates a loser devil in The Screwtape Letters. Screwtape is a grumpy old demon with No Sense of Humor, whose list of things he can't stand about Heaven includes God's disgusting, hedonistic love for His physical creations, not to mention His habit of playing music at all hours of the night. Screwtape can't actually hear the music, he just hates the fact it is being played. Silence is no improvement, as Screwtape prefers some good, loud, decently ugly noise. Meanwhile, he works a desk job as an undersecretary in Hell's middle management, on one occasion signing his name with a pretentious string of honorific letters. (Hell, of course, is a Vast Bureaucracy.) His nephew and apprentice Wormwood is even more of a loser, sent on a mission to tempt a mortal, but making mistake after mistake, getting his uncle in trouble, and eventually failing miserably.
- This is half the point of The Devil's Storybook and The Devil's Other Storybook, both by Natalie Babbitt. The other half is how he still wins as often as he loses.
- Andrew Wyvern in James Morrow's Only Begotten Daughter is a fairly disgusting creature, who only seems to succeed because God's an absentee landlord. Morrow stated in interviews he was trying to avoid the various tropes so the Devil wouldn't be the most interesting character.
- Left Behind has the devil so incompetent that he becomes sympathetic solely because of how badly he gets beaten. He tries to turn things around, but he was destined to lose at God's hand anyway.
- Lucifer in The Book of Joby is fairly petty, and gets crapped on by birds.
- In Paradise Lost, despite Satan's fancy rhetoric and impressive figure, he's just posturing as an epic hero and making self-defeating arguments and that he's simply too proud to ask for forgiveness and admit his mistakes in front of all his loyal followers. Even in the battle scene he gets clobbered unconscious the moment he takes the field. Its sequel, Paradise Regained, continues this, in part to fit into the idea of damnation as continually degrading him into weaker and less godly forms, and also because he was up trying to tempt Jesus and was obviously doomed to failure, unlike with Adam and Eve.
- Chichikov from Dead Souls definitely invokes this with the whole "buying people's 'souls'" thing and he's a lot like the "devil as small time bureaucrat / loser" portrayal in other works. In fact, both Chichikov and Scratch store their souls in a box - the only difference is that Chichikov's are metaphorical.
- Torak of The Belgariad and Azash of The Elenium. Both are incredibly powerful in physical/magical terms, but they're also crippled, handicapped by an inability to change, stupid, and totally unable to understand human emotions, which ultimately results in both their downfalls.
- Although the Devil wins in the short story Enoch Soames, the narrator characterizes him as a humorless, self-important prig, describing him variously as a Dastardly Whiplash type- attempting to seem cool and sinister but really looking like a melodrama villain as well as a "swell mobsman"- slang for a type of pickpocket/petty criminal that dressed in fashionable clothing to blend in.
- The devil appears in the "The Stones Are Hatching" as a blot of pure darkness who comes to take the soul of Alexia's teacher in a flashback. However, he quickly turns out to be just as stupid as his folkloric counterpart when he is easily convinced by the teacher into going after his students instead, and then cannot even tell the difference between Alexia and her shadow, taking that instead.
- In Brimstone Satan is shown to be not only an incompetent jailer (letting over a hundred damned souls escape Hell), but he's also incredibly petty and juvenile, unable to pass up an opportunity to tie someone's shoelaces together or loosen the cap on a salt shaker.
- In Buffy the Vampire Slayer, Caleb, right-hand man to the First Evil, refers to Satan as a "little man" (at least, compared to his boss).
- Doctor Who: In "The Satan Pit", when the Doctor confronts the Beast in his prison, he finds a towering red-horned monstrosity that roars at him and shoots fire. Then he realizes that the Beast is just that, a simple beast, with its spirit and sentience gone elsewhere. The physical body of the Beast suddenly becomes a lot less scary.
- On Good Eats this happens sometimes. Sometimes a Big Red Devil will appear and get his ass kicked by Alton (who at the time was a Christian in Real Lifenote ). Or, as in the Devil's Food Cake episode, he simply will not get to taste the cake.
- Millennium has the four demons at the coffee shop in "Somehow, Satan Got Behind Me", revealing that for all their fearsome rep in the show, demons are... kind of pathetic. Even Frank ends up feeling sorry for one of them.
- In the Mystery Science Theater 3000 episode "Santa Claus" Mike Nelson sings "The Devil is a Wiener" to the tune of the soundtrack.
- In an episode of Northern Exposure, the town is visited by Satan, who is a dumpy and unimpressive man more interested in small acts of betrayal than diabolical evil. He ultimately fails to corrupt the citizens of Cicely even slightly.
- In the Quebec surreal comedy sketch show Phylactere Cola, one skit shows Satan living in a basement apartment, having to deal repeatedly with annoyingly persistent Jehovah's witnesses. They manage to convert him in the end!!
- Saturday Night Live:
- One sketch features a musician making a Deal with the Devil only to discover that Satan is a phenomenally crappy songwriter.
- Another one features Patrick Stewart as an initially impressive Satan who then chokes on a grape and finds that he can't command any respect from his lackeys anymore.
- In another episode the Devil goes on The People's Court suing for a woman's soul. He loses.
- Supernatural: Lucifer is a suave, sophisticated, and exceptionally dangerous being. He created the demons personally, can destroy the planet when at full power, and is one of five creatures that the Colt can't kill. But ultimately, none of that changes the fact that he's just a spoiled brat throwing a tantrum because his daddy wasn't paying enough attention to him.
- There's a The Whitest Kids U' Know routine in which the Devil is depicted as an effeminate Southern guy who spends two minutes of screentime going on what Wikipedia calls "unprecedented rants against people who make assumptions of what the Devil is".
"Would you please stop that?"
- On an episode of X-Play about the time a World of Warcraft expansion came out, Morgan made a deal with the devil to have him level up her character. Unfortunately, the Devil sucks at WoW.
- The song "The Devil Went Down To Georgia" by The Charlie Daniels Band portrays Satan as "way behind" on his quota for souls. In desperation, he makes a bet with Johnny, a local Georgia fiddle player, to a fiddling contest. Though Satan is portrayed as a pretty badass dude, he's no match for a good ole Georgia boy and gets beaten handily. Johnny freely gloats and insults the devil throughout the song and ultimately snags his shiny golden fiddle. It's speculated that the Devil's true goal was making Johnny fall to the sin of pride, and indeed Johnny acknowledges that he knows what he's doing is a sin, so whether he was truly prideful or just confident in his abilities is up for debate.
"The boy said, 'My name's Johnny and it might be a sin,
But I'm gonna take your bet! You're gonna regret, 'cause I'm the best that's ever been!'"
- A sequel balled: "The Devil Comes Back To Georgia" also made by the Charlie Daniels band tells of how ten years after the Fiddle Duel, the Devil challenges Fiddle Player Johnny, now a family man and father, to a rematch. Seething from his defeat years before, the devil tells Johnny that his pride will be his downfall and takes the Golden Fiddle away as Johnny is tuning it, though the Fiddle player still has his old fiddle in his woodshed. After getting warmed up on his old fiddle due to having not been playing since the birth of his son, Johnny and the Devil duel once again. Its' not clear at the end, but from the sounds of things, Johnny kicked the Devil's ass... again.
- Then there is the Trope Namer itself, which is Lordi's song The Devil Is A Loser. The song ridicules someone for making a Deal with the Devil... because they were stupid enough to make a deal with someone that pathetic.
- The lyrics are also boastful in nature that Mr. Lordi (the singer's persona) is the more powerful being that the people in the music video should be fearful of.
- The song "War is my Destiny" by rapper Ill Bill describes the fallen angels who served Satan during the rebellion as promptly dethroning him after they were cast from Heaven for his failure to deliver on his promises. A new Devil is crowned in his place. Satan later manages to somewhat redeem himself in their eyes after the Biblical Flood by coming up with a plan to corrupt mankind by manipulating them through the word of God.
- Stryper's (Christian glam metal band) To Hell With the Devil dismisses the Devil from a Christian perspective.
- Similarly, many of Carman's songs fit this particular trope as well.
- "The Number of the Beast" by Iron Maiden was perceived by some to out the band as Satan worshipers... the song itself plays out like a horror movie (it was inspired by Damien: Omen II). However, the "Run to the Hills" single artwork has Eddie, Maiden's zombie mascot, in a fight with the devil. The Number of the Beast album shows the aftermath, Eddie holding the Devil's decapitated head. Maiden rightfully pointed out that they were not encouraging worshiping the Devil as he was the LOSER in the battle.
- "Bigger Than The Devil" (especially the cover art) by SOD clearly implies this.
- The Psychopathic Records supergroup "Soopa Villainz" has Mr. Diamond (Violent J) reference this trope in their Boastful Rap "Conquer"...
Mr. Diamond: "I don't work for the Devil!
Shit, we kicked him outta Hell!
We overthrew him, stabbed him with a cross, and cut off his tail!"
"We so deep underground, the devil came around
- From the Insane Clown Posse's "We Like It Like That":
But got his tail chopped off by Shaggy the clown"
- Both members of ICP are religious, so it's no surprise Satan (or "the Witch" as he's often called) is portrayed this way. At no point in any of the Joker's Cards is the Witch shown having any powers greater than lies and deception.
- The song "Beelz" by comedian Stephen Lynch depicts Satan as Affably Evil and Ambiguously Gay.
- The Trevor Moore song High in Church is about Trevor and his friends indulging in several hallucinogenic substances before getting roped into attending church by his mother. The majority of the song is about Trevor (who is growing increasingly-more paranoid as the drugs gradually kick in) expressing worry that somebody will know he's high, coupled with a bit of commentary on the more "fire and brimstone" aspects of Christianity while still acknowledging the nice parts of the religion. Finally, the shrooms he ate kick in and Satan (or just a hallucination of him) appears to taunt Trevor with a promise of eternal damnation. Trevor, suddenly not afraid anymore, rips Lucifer's taunts apart with a very logical and epic Kirk Summation and sends the devil screaming back to Hell.
Satan: For all eternity, you will never escape my clutch!
Trevor: Okay, uh, first of all, I think that seems like a little much. A joint and a couple caps and stems, is that all that a soul is worth? And God made everything I've done tonight, all of it's from the Earth! The mushrooms and the pot, yo, He made it ALL! The nitrous! And the adderall! My soul relaxers, maybe a little coke, but if that damns me for eternity then if you ask me the system's broke!
- "The Devil & Me" by Clutch describes a down and out devil from alternating perspectives. Opening with:
The devil and me had a falling out.
Violation of contract beyond a shadow of a doubt.
Wherever he go, whomever he meet.
He got to cross my house on the other side of the street.
- Generally, if you read Medieval folklore about the Devil, he will usually be presented as a diminutive, ugly and stupid, easily tricked by ordinary peasants on a daily basis. The more powerful, imposing Devil only started emerging during the Reformation period when religion went from a fairly laid back routine back to Serious Business.
- In Zoroastrianism, The Anti-God Ahriman is usually portrayed as a self-destructive moron, who frequently suffers indignities like being anally raped (Vendidad). This is because evil in Zoroastrianism is held to be inherently self-defeating, so while in practise he is as powerful as Ahura Mazda he won't truly accomplish anything. Interestingly, Ahriman is the predecessor of Satan, as Zoroastrianism indirectly influenced Second Temple Judaism, but the idea of Satan as a loser evolved independently.
- In Islamic culture (as opposed to the religion of Islam, which doesn't have much to say about the Devil other than "he's a jinn and a tempter") the devil (called Iblis, who was never an angel) is not only stupid but ugly as well which makes a folk theory/Alternative Character Interpretation that he and God were once lovers kind of odd. Then again, Love Makes You Crazy, Dumb, and Evil. The idea doesn't appear in religious text and is in fact regarded as heretical. It's folklore, don't think too hard about it.
It's been said (eg. by Karen Armstrong) that when Ayatollah Khomeini called America the "Great Satan", in an Islamic context that referred more to this trope than the idea of a supreme evil, with the Islamic "Satan" being a materialistic dumbass with no spiritual values.
- In Mormonism, the Devil is the loser of the war in heaven. Basically, it boils down into different versions of the Plan of Eternal Salvation. Lucifer's plan involved everyone not having free will, guaranteed entry into heaven, and the glory for all of that belonging to himself since it was his plan. Jesus wanted everyone to have free will even though it meant that yes, there will be sinners and evil people, as well all the people going into heaven deserving it for trying act ethically over the course of their lifetime and all the glory going to God because God enabled it and probably had it all in mind anyways. Lucifer eventually becomes Satan, stewing in Outer Darkness (Hell) and trying to upset the Plan of Eternal Salvation at every chance he can get. Which, of course, helps to enable the entire thing. He's still treated as a very dangerous character. Yeah, he's lost, but his goal shifted from elevating himself above God by forcing humanity into salvation, to taking as many souls down with him as he can. In other words, a temper tantrum because he can't have things his own way.
- Irish folklore tends to portray the Devil as a total sucker who will buy just about anything. This is in contrast with other traditions where a Deal with the Devil will end up with the person who made it being the fool, thinking they could trick the devil. In most stories, the protagonists will get away with swindling the devil without consequences and souls intact, and in the few where they do suffer some consequences, they tend to result either from character flaws on the part of the protagonists or the devil being a sore loser. For instance, the tale of Jack O'Lantern, where he ensured that he could not be taken to hell but neglected to make sure that he could get into heaven, and for this oversight will eternally wander the earth, carrying a lantern to keep evil spirits away. It's not surprising for a culture that evolved wordplay to an art form and considered that if someone was swindled it was the victim's fault for being an idiot. St. Patrick may have changed that (driving the snakes/liars from Ireland), but early Irish Christians, reading the Bible, seem to have been very unimpressed with the devil's intelligence by comparison. Swindling the devil is still acceptable, with the ordinary human protagonists playing Karmic Trickster.
- Note that US culture is heavily influenced by the Irish one, particularly in the Northeast (with the large Irish Catholic immigration in the 19th century), and in the South (where Ulster Scots and Irish Protestants settled in the 17th and 18th centuries), so it isn't surprising that American culture is also riddled with tales of the Devil getting tricked by humans: see e.g. "The Devil Went Down to Georgia" in Music above, or the Northern equivalent, "The Devil and Daniel Webster" and variants (which combines it with the American and especially Northern focus on legalism and quibbles).
- Finnish folklore has one prominent story about the Devil. The bargain he makes is that the story's protagonist will work at his farm for three years, and the first of them to lose their temper will be partially skinned, enough to make a pair of boots. The Devil is depicted as a land-owning farmer, and over the course of the story loses his dog, his oxen, two wives, and his house to The Protagonist. He is on the verge of running from his own home during the night when the second wife is killed, making him finally lose his temper, so the protagonist wins the arrangement and gets exactly what he bargained for: a pair of very nice shoes made with the Devil's skin. The Devil, on the other hand, vows to never again bargain with a Finn, because they are too stubborn.
- There's a folk tale about The Devil and the Farmer's Wife, where the farmer lets the devil take his wife, but soon wants to give her back. Sometimes, the farmer can live with her even though the Devil can't (either he's just more patient or the wife deliberately made more of a nuisance of herself in hell) and he leaves the family alone; in other versions, the farmer doesn't want her back either and they split up, while the Devil still leaves the family alone. Either way, the devil is not particularly impressive.
- Phil, the Prince of Insufficient Light from Dilbert. He even has a giant spoon in place of the usual pitchfork, and claims to be from Heck. He's in charge of punishing small sins, like leaving the toilet seat up. He's a half-brother to the Pointy Haired Boss (and the Pointy Haired Boss was always their mom's favorite).
- From The Far Side:
The Devil: (staring out his home window) Tell me, Margaret... Am I a butthead?
- Swedish comic Himmlens Änglar has poor Fan who is this to such a degree that he's The Woobie.
- Satan in Old Harry's Game is a rather whiny fellow who uses torture and corruption mainly as mechanisms to cope with his own self-hatred.
- The Ebon Dragon from Exalted is basically the Devil-figure of the setting; the master of betrayal, lies, and deceit, and the only one of the Yozis who operates on standard human morality...but see Word of God's explanation for exactly why his villainy is represented not by alternative interpretations of the Virtue system, but merely by having bad Virtue scores:
"The Dragon's evil is supposed to be pathetic. It's supposed to be contemptible. That doesn't make him weak, but he's not heroic in either a classical or contemporary sense. He's a force of evil without scruples or principles. He stands for nothing save making things worse for everyone. He will stab you in the back at every turn and he cannot be reformed. ... When you face the Dragon, having Virtues greater than him, you can look down on him. You can see that he's not simply different or alien, but a loser. And yet, losers can win. He's a smart loser, a cunning loser. He's a loser unfettered by any moral restraint holding him back from hurting you any way he can get away with. He cheats. He cheats very well. He might just win. But it won't be a heroic victory. To make it so would miss the point. He's giving the finger to all the humanists and transhumanists and alien weirdos. He says you all suck. But the truth is that he just sucks compared with all of you and on some level, he knows it. I said there were two bad things that alternative Virtue did as a model for the Dragon's wickedness. The second is that you give him an excuse. Oh, he runs from fighting? Actually, he's just smart enough to duck out when he's losing. It's all very reasonable, you see. No. Wrong. He's a coward who bolts in terror from the heroes and lies to himself and others about why he did it. Even if he can make himself stay as an act of antagonistic defiance, he can't make himself stop being terrified. He can't escape into the Other. He's stuck playing in the same moral sandbox as everyone else and he absolutely fails at it."
- The Infernoids are something of a meta-example, an archetype of Fiends that look like mechanical devils, named after Biblical demons. While powerful, all of them are NOMIS, who must be summoned by first banishing other Infernoids from your Graveyard, making this a weak archetype (or at least a very hard one to master) when they are used alone. Enforcing the Trope even more, while the most powerful one is Level 11, the one named after Satan is Level 1, with zero ATK and DEF, unable to be used offensively and not much use by itself.
- The Burning Abyss Fiends are a group that can cut it by themselves; so long as they have help from the two members of their group who are not Fiends, which are based on Dante and Virgil. Without them, the Graveyard activation requirements of their effects is difficult at best.
- Played with in kill puppies for satan; the devil himself is legitimately evil and possibly dangerous, but his human minions are all pathetic, incompetent losers who think kicking puppies around is the evilest thing they can do. He also has to put up with demons unionizing on him and scoring an exclusive work contract, much to his chagrin.
- In Antonin Dvorak's opera The Devil and Kate, the sheer bitchiness of the chatterbox Kate is such that even Lucifer is afraid of her, and is willing to do anything in order to send her back to Earth.
- In Randy Newman's musical/opera Randy Newman's Faust, Lucifer sings a song called "Bleeding All Over the Place." He's not a totally loser, but he's a heck of a lot less threatening than the Ultimate Evil usually is, possibly because he's voiced on the CD by Randy Newman.
- Conor McPherson's play The Seafarer, has a character named Mr. Lockhart who is clearly a stand-in for good old Mr. Mephistopheles. He wastes an entire evening playing cards with a bunch of guys, some of whom are alcoholic, just to get one soul while tormenting him about his impending fate as much as possible, which truthfully is something typical for him, but this NOT what makes him come across like a loser. No, what proves it is the exact WHY of his predatory behaviour which becomes clear during a slowly-building Villainous Breakdown, where he all but openly cries about how much suffering his own choices have caused him and how sharing this suffering with the men that he manages to get his hands on is the only thing left to him.
- Demise is presented as a Satanic Archetype in The Legend of Zelda: Skyward Sword, but he was defeated in his war against the god Hylia long before the game started. He manifests himself as the mindless Imprisoned three times, but always loses to Link. Upon being restored to a humanoid form, he takes on Link in a swordfight and loses once again. He curses the future incarnations of Link and Princess Zelda to be plagued by Ganondorf, for eternity, but even he has yet to achieve a permanent victory over the two.
- In the Sam & Max Beyond Time and Space episode "What's New, Beelzebub?", Satan is a rather ineffectual middle management of Hell, LLC. He has no respect from his subordinates, and is at the beck and call of the Big Bad, who eventually fires him.
- Satan from Puyo Puyo and Madou Monogatari is a pathetic Stalker with a Crush for protagonist Arle Nadja. His schemes are frequently ridiculous or pointless (such as increasing the power of the sun so he can get a tan and attract girls), and is always foiled by her and Carbuncle.
- Sunless Skies has the colony of Devils living at the Well of the Wolf. The place is so horrible they're actually relatively selfless and helpful simply because they're to worn down by living there to be evil anymore. It's implied that Chorister Bees use Devils as a chrysalis and these are the ones that the bees hatched from, which may contribute to their condition. Upon witnessing this, the Repentant Devil is visibly shaken to see what the Devils have been reduced to after the Exodus.
- Pony Island: Lucifer sucks at basic coding, game design, and is obsessed with girly ponies. He kidnaps souls and makes them play his games because they're just that bad.
- In the True Cheater ending of Catherine, Catherine's father, the demon Nergal appears when Vincent proposes to his daughter to try to intercede. He's completely harmless, gets kicked in the nads by his daughter for interrupting, seems more concerned with playing video games, and ultimately gets overthrown by Vincent when he turns into an Incubus and takes over Hell. The ending's last shot shows him being used as a couch on which Vincent and Catherine are making out.
- The Devil is presented as a large and imposing figure in Cuphead (and he very much is), but at the very last portion of his boss fight, he starts crying like a baby, complete with stereotypical "waaaah, waaaah" sounds. That doesn't mean you've won, however. It just means that now you have to keep shooting him while dodging his tears.
- The Devil from Dinosaur Comics spends all his time talking to T-Rex about video games and internet slang, and he drinks grape juice from concentrate.
- Hell Inc: in Hell, Inc. B.L. Zebub is a classic red, horned demon who works in an organization based around the torture of damned souls and delights in tormenting anyone under him in the hierarchy. He is also trapped in middle management, breaks his work PC by visiting sketchy porn sites on a regular basis and is the frequent target of unflattering drawings and jokes by his employees.
- Pictured above is the Devil. While he IS a pretty badass dude, more than a few strips feature him collecting mockery of God, taunts of Ezekiel and Ariel "the Wascally Angels", pity of Buddha and made aware that he's Lonely at the Top. The closest thing he had to a friend was his son Loony Fan L'il Evil, a Harmless Villain whose faith might as well have been Ho Yay. Characterization Marches On however, and later story arcs have made him into a much more serious villain.
- The Anti Christ was so pathetic that he finally got a life only after accidentally mind-wiping himself by drinking from Lethe and so far no one (including Devil) wanted his old personality back.
- In Sluggy Freelance, Satan is the victim of cyber attacks by Riff, ends up doing the nasty with a cat while drunk, gets chewed out on a daytime talk show for not taking care of the resulting demonic kitten children, and is terrified of scorpions.
- In the Rooster Teeth Comics, Hell is tech support for Apple, the Devil is the still the Boss, but he wears Khakis.
- In Dead Duck, the devil is a teenager running Hell so he can appease his old man and running a day camp on the side under a costume to look more intimidating. His father? God
- Inverted in Holy Bibble. Although the real God is pretty awesome (and has a lot of personal similarities to Satan, actually), the God described in the Old Testament is actually a senile and useless minor demon created by Satan on a whim.
- Once faced with Tennyo and Generator in the story "Sit In" in the Whateley Universe, the demon lord (okay, brevet under-baron) Phesclangorenthal rapidly turns into this.
- Discussed by Moviebob, who believes that when you take away all the stories and rumors, the devil is less Lex Luthor, and more Starscream.
- In Bonus Stage, Satan rambles on about nothing and makes people watch Time Squad, watch Shrek 2 or eat his mom's spaghetti. He also lets Joel, Phil and Elly out of hell.
- In later episodes of Vinny's Tomodachi Life streams, Satan ends up moving to Vineland Island. He quickly makes lots of friends, wears a basketball jersey among other ridiculous outfits, and lives in a brightly-colored apartment. Vinny freely admits that this is the least threatening version of Satan he's ever seen.
- In Hellsing Ultimate Abridged, Satan (who shows up in Episode 8 when Alucard ends up confronting God) is actually a soft-spoken and not particularly forceful guy who hesitantly asks God to ease up the requirements for going to Heaven and offers Him some avocado toast if He'll come by to visit sometime. Satan also asks Alucard to give him back the Hounds of Baskerville, but Alucard cuts him off by yelling that "They're mine now!"
- The Red Guy With No Pants from Cow and Chicken and I Am Weasel. He certainly looks the part but he's only referred to as the devil in the first show's pilot (in which his "Evil Plan" is to make Chicken smoke cigarettes).
- On South Park, Satan may look scary, but he's not.
- He used to be scary, but then got into an abusive, codependent relationship with Saddam Hussein and hasn't recovered since. At times, his demeanor borders on self-sabotaging, making him more of a woobie. Then he had enough and killed Saddam. But Saddam came back because he's already dead.
- Amusingly, God Himself called him out on this:
God: Jesus, what the hell happened to you?
God: You got kicked out of here for being a headstrong rebel. And now you're a whiny little bitch.
- The Robot Devil from Futurama. The guy is outsmarted by Fry and in one episode is seen in jail. He's also whiny, Screams Like a Little Girl when you hit him with a fiddle, and lives in New Jersey. His only positive trait is that he's a good musician.
- Played with in "The Devil's Hands Are Idle Playthings", which starts with the Robot Devil losing at his own game and being forced to give up his own hands to Fry, but then has him pull off an intricate Chain of Deals that ends with him getting his hands back and Fry humiliated in front of a crowd. Say what you will about him, the guy is pretty competent at manipulative bastardry.
- In God, the Devil and Bob, The Devil is shown more as an incompetent and effeminate weirdo with creator issues than a powerful master of temptation. His evil schemes are often self-defeating but occasionally he proves he's a Not-So-Harmless Villain.
- Jimmy Two-Shoes: Lucius is technically only the great-great-great-great grandson of the original devil, who is feared by everyone including his descendants. Lucius himself is largely a Smug Snake Harmless Villain who is incapable of running things without Heloise. He's also a massively Large Ham, because he is voiced by Sean Cullen.
- Played with in Lucy, the Daughter of the Devil: Satan seems like a harmless yuppie right up until the point where he tries to murder you in your dreams with burrowing flesh-worms.
- The Powerpuff Girls makes this a Subverted Trope. Him may mince around in drag between launching invariably doomed Evil Plans, but he is far from harmless. An immortal Reality Warper, Him only loses because his schemes hinge on exploiting some character flaw, a Monster of the Week, or poorly-chosen combat conditions. He comes far closer to success than other villains, and one particular episode demonstrated exactly what would happen should the girls fail...
- In The Simpsons, whether he's a loser or not is a case-by-case basis:
- He's certainly a loser in the Treehouse of Horror segment "The Devil and Homer Simpson", where his own Jury of the Damned rules against him after he's outwitted by Marge.
- In one canon episode, where Springfield's single people tried to change the law to make the town less family-friendly, Marge decided to lead a campaign to stop them. A tobacco company representative offered her a cheque. Once she took it, the representative took off his hat, revealing a pair of horns, assumed a more devil-like appearance in general and claimed she belonged to them. She quickly pointed out she hadn't endorsed the cheque and the representative quickly resumed his human look and claimed the horns were "football injury".
- In Ugly Americans, the demon Twayne Boneraper makes a deal with a politician that he'll become mayor in exchange for his soul. Unfortunately said politician is utterly unelectable and boasts openly about having made a deal with the devil. He ends up dying accidentally, putting Twayne up before the demonic court for being a failure as a demon, as the only soul he's managed to ensnare recently is that of a large, ill-tempered cat.
- In an episode of Darkwing Duck, the Devil plays dirty, tricking Gosalyn into signing the pact that lets him claim Darkwing's soul. The problem? Morgana and her clan manage to beat him at his own game and find a loophole in it!
- In the Pinky and the Brain Halloween episode, the devil offers Brain the world in exchange for his soul. Brain refuses because he's angry about being called a failure, but later finds out that the gullible Pinky has been persuaded to sign in his place, in exchange for a "radish rose watchamahoozit." However, the devil is forced to release Pinky when it turns out that he doesn't even know what that is.
- In the Rick and Morty episode "Something Ricked This Way Comes" (actually a parody of Needful Things) Summer gets a part-time job at the Needful Things thrift store, which seems to be a lot like it was in the book, until Rick immediately figures out that Mr. Needful is actually the Devil, and that the golden microscope he sells is cursed. Rick is able to use his mad science to figure out how to detect, analyze, and counteract curses, and he opens up his own store across the street where he removes curses, leaving the items with just their beneficial magic. For instance, an aftershave that makes a man irresistible to women, but also leaves him impotent? Rick pairs it with a cure for impotence. Rick makes a ton of money, and Mr. Needful is so humiliated that Summer has to talk him out of suicide.
Mr. Needful, the Devil: "People like Rick are making me obsolete. I mean, seriously. I may be 'the devil', but your grandpa is the devil."
- Rocko's Modern Life gives us Peaches, Dark Overlord of Heck...who gets bossed around by Heffer's late grandma and isn't actually the ruler of Heck.
- The Flintstones: Pebbles and Bamm-Bamm's song "Let The Sun Shine In" (from the episode "No Biz Like Show Biz") is pretty much this.