Mephisto: If you so desired, I could return your mother to you, alive and well. I could even mend your relationship with your brother— make your family whole again. All I would require is— [finds Ebony pressed against his neck] Gyark! 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 perhaps he's unattractive and unpopular and lives in his mother's basement. Perhaps he's 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.
This is the other side of the infernal coin. Satan as a stylish, seductive badass is a modern invention. Medieval portrayals have him a thug, dangerous but also easy to fool and really only waiting for someone stupid enough to sin. Older ones portray him as something of a celestial prosecutor, someone appointed by God (or at least permitted) to put humanity to the test; opinions differ on whether it's simplya duty or if he is a jerkass who loves his work.
For other non-threatening evil spirits, see Don't Fear The Reaper.
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Anime and Manga
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 MgRonald?
Neron loses because Captain Marvel's soul is too pure. He also loses his throne in the Reign in Hell comics.
Satanus joins Neron as a Devil who is 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. On the other hand, he helped save about three universes from destruction at the hands of said "old man", so maybe he had a reason for quarreling with him.
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. Then in Thunderbolts he gets completely played and humiliated by the Leader and 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 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.
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 avoidthe varioustropes so the Devil wouldn't be the most interesting character.
Lucifer in The Book of Joby is fairly petty, and gets crapped on by birds.
The underlying characterization of Satan in Paradise Lost. Despite his fancy rhetoric and impressive figure, he's just posturing as an epic hero and making self-defeating arguments that even he admits are bogus. 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. Of course, there are a lot of people who see him as exactly the epic hero he presents himself to be.
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.
Live Action TV
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).
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.
At one point, he calls the three lesser devils "Insignificant piles of insect saliva." The one of the lesser devils, played by Norm McDonald asks, "How exactly do you pile saliva?"
After choking on a grape following his threat to eat their bloody entrails, another minion played by David Spade tells him that he shouldn't attempt to eat bloody entrails until he mastered grapes. They keep on mocking him even after he turns them all into barnyard animals.
In another episode the Devil goes on The People's Court suing for a man's soul. He loses.
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.
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.
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!!
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.
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 three creatures that the Colt can't kill (the other two are implied to be God and Death). However, when it comes right down to it, none of that changes the fact that he's a spoiled brat throwing a tantrum because his daddy wasn't paying enough attention to him.
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.
On Good Eats this happens sometimes. Sometimes a Big Red Devil will appear and get his ass kicked by Alton (who is a Christian in Real Life). Or, as in the Devil's Food Cake episode, he simply will not get to taste the cake.
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 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.
"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 The Omen). 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.
"We so deep underground, the devil came around 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.
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.
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).
"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."
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 Mc Pherson's play The Seafarer, the Devil is a character named Mr. Lockhart. He wastes an entire evening playing cards with a bunch of guys, some of whom are alcoholic and one of whom is blind, just to get one soul.
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.
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.
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
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 Movie Bob, who believes that when you take away all the stories and rumours, the devil is less Lex Luthor, and more Starscream.
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 SnakeHarmless 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.
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 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.