[[quoteright:166:[[Webcomic/{{Sinfest}} http://static.tvtropes.org/pmwiki/pub/images/sinfestloserdevil_1374.png]]]]
[[caption-width-right:166:Keep telling yourself that.]]

-> '''[[ComicBook/GhostRider 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!\\
'''[[VideoGame/DevilMayCry 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.
-->-- ''VideoGame/MarvelVsCapcom3''

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 ''JustForFun/AvatarAndTheAirbendingFellowshipOfVampireSlayers'' than punishing the damned or tempting mortals, or perhaps he's unattractive and unpopular and [[BasementDweller lives in his mother's basement]]. Perhaps he gets outsmarted every time he tries to [[DealWithTheDevil make a deal with a mortal]]. Maybe he's plagued by DaddyIssues (being the original rebel and all).

Naturally, he's no match at all for the forces of heaven. [[KungFuJesus Jesus doesn't need to know kung fu to humiliate him]] and is in any case [[JesusWasWayCool much cooler than him.]] His former fellows among the angels can give him wedgies at will. A GoodShepherd can [[TalkingTheMonsterToDeath talk him into submission]]. Heck, even a mortal guy with a cross could drive him back.

Some works will use EvilIsPetty 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.

If the Devil's job sucks enough then he may decide to leave it to someone else altogether; see ToHellWithThisInfernalJob. If the Devil sucks at his job enough then someone else might take it from him; see HellHasNewManagement.

This is the other side of the infernal coin. Satan as a stylish, seductive badass is a modern invention. [[FairyTale 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 [[PunchClockVillain simply]] [[NecessarilyEvil a duty]] or if he is a {{jerkass}} who loves his work.

For other non-threatening and also non-evil spirits that personify death, see DontFearTheReaper.



* In [[https://www.popsugar.com/fitness/Halo-Top-Ice-Cream-Commercial-43695801 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 [[HypocriticalHumor loves it too much not to eat it himself]].) The storyline continues in later commercials, where [[https://www.youtube.com/watch?v=hnoxJuVx11k he tries to sue the angel]] with a team of [[AmoralAttorney damned lawyers]], failing again because ''they'' can't stop eating it either, and later [[https://www.youtube.com/watch?v=lkY_Fjr4T6o&index=2&list=RD3fm3BGLQRCg a third]] where he offers to [[TakeThat stop making Segways]] if the angel stops making the ice cream.

[[folder:Anime and Manga]]
* In ''LightNovel/TheDevilIsAPartTimer'', the Demon King and TheDragon 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 [[WcDonalds Mg]][[BurgerFool Ronalds]]?
** Downplayed by the fact that he enjoys his job, takes his fall from power remarkably well, and is a charismatic NiceGuy. He's also not the biblical devil; Satan is a very common name among demons.
* In ''Anime/PuellaMagiMadokaMagicaTheMovieRebellion'', [[spoiler:Homura]] becomes a self-admitted demon who hates the world and ([[MoralityChain almost]]) everyone in it. But, for all her power, she isn't ''happy''. [[spoiler:Fundamentally, she is still the same alienated, self-hating pessimist we met in the first episode.]] Even her servants pelt her with tomatoes.

* Neron, Creator/DCComics's version of the Devil, fits often:
** In ''ComicBook/UnderworldUnleashed'', 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 ''ComicBook/OneMoreDay'' below. After many of Franchise/TheFlash's old villains CameBackWrong (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 ''ComicBook/{{Lucifer}}'' has an AlternateCharacterInterpretation 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.
* Mephisto has his ups and downs.
** He was enslaved to Thanos during ComicBook/TheInfinityGauntlet saga. He was once humiliated by the ComicBook/BlackPanther by being cut off from his power and the crap beat out of him. He was OutGambitted by Doctor Doom, and even bested by his own son, [[AntiAntiChrist Damien Hellstorm]]. Then in ''ComicBook/{{Thunderbolts}}'' he gets completely played and humiliated by the Leader SelfDemonstrating/{{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 ''ComicBook/OneMoreDay'' he dissolved the marriage of Spider-Man and Mary Jane. He once faked defeat against the ComicBook/IncredibleHulk 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, [[ComicBook/TheMightyThor Hela, and Loki.]]
* ''ComicBook/{{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 ComicBook/GhostRider 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 ''Literature/TheLordOfTheRings'' {{Mary Sue Hunter}}s story ''Fanfic/TheGameOfTheGods''. In it, [[GodOfEvil Morgoth]] attempts to derail the books by inserting various {{Mary Sue}}s 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, [[IneffectualSympatheticVillain he's become rather pitiable]].

* ''Film/{{Bedazzled 1967}}'' contains possibly the most literal example ever, in which Satan [[spoiler: loses a wager with God and is sent to a VillainousBreakdown]].
* In the ''Film/{{Bedazzled 2000}}'' remake the Devil [[HotAsHell (a beautiful woman)]] grants wishes to a man in exchange for his soul, but each wish [[JackassGenie results in a humiliating failure]]. It turns out that the Devil is actually harmless, since [[spoiler: God owns all people's souls; they can't be sold!]] She's just a practical joker.
* ''WesternAnimation/TheHauntedWorldOfElSuperbeasto'': 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 ''Film/TenaciousDInThePickOfDestiny''. Old Scratch wins the rock off here against the two protagonists (and his performance here is ''[[EvilIsCool wicked awesome]]'', hammed up by Music/{{Nirvana}} drummer Dave Grohl, who portrays him) but hes OutGambitted in the end and banished back to Hell by the duo anyway.
* In the Brazilian movie ''Film/OAutoDaCompadecida'', the Devil appears as an AmoralAttorney 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, TheHero [[FearlessFool makes fun of him all the time]] because he [[EvilSmellsBad 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 ''Literature/TheDivineComedy'', 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 [[SelfInflictedHell cools and hardens the tears into ice, trapping him]].
%%* Creator/EoinColfer novel ''Literature/TheWishList''.
* ''Literature/TheBrothersKaramazov'': 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 HeroicBSOD. 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' ''Literature/{{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 [[EvilIsPetty 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.
* Creator/CSLewis creates a loser devil in ''Literature/TheScrewtapeLetters''. Screwtape is a grumpy old demon with NoSenseOfHumor, 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 VastBureaucracy.) 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 [[DevilButNoGod God's an absentee landlord]]. Morrow stated in interviews he was trying to [[DracoInLeatherPants avoid]] [[DesignatedVillain the various]] [[MisaimedFandom tropes]] so the Devil wouldn't be the most interesting character.
* ''Literature/LeftBehind'' has the devil so incompetent that he becomes sympathetic solely because of how badly he gets beaten. He tries to turn things around, but [[YouCantFightFate 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 ''Literature/ParadiseLost'', 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, ''Literature/ParadiseRegained,'' 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 ''[[JesusWasWayCool Jesus]]'' and was obviously doomed to failure, unlike with Adam and Eve.
* Chichikov from ''Literature/DeadSouls'' 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 ''Literature/TheBelgariad'' and Azash of ''Literature/TheElenium''. 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 ''Literature/EnochSoames'', the narrator characterizes him as a humorless, self-important prig, describing him variously as a DastardlyWhiplash 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 "Literature/TheStonesAreHatching" as a [[EldritchAbomination 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.

[[folder:Live Action TV]]
* In ''Series/BuffyTheVampireSlayer'', Caleb, right-hand man to the First Evil, refers to Satan as a "little man" (at least, compared to his boss).
* ''Series/SaturdayNightLive'':
** One sketch features a musician making a DealWithTheDevil only to discover that Satan is a phenomenally crappy songwriter.
** Another one features Patrick Stewart as an initially [[LargeHam 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.
* In an episode of ''Series/NorthernExposure'', 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.
* There's a ''Series/TheWhitestKidsUKnow'' routine in which the Devil [[NoCelebritiesWereHarmed is depicted as an]] [[Creator/ChrisCrocker effeminate Southern guy]] who spends [[OverlyLongGag 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 ''Series/XPlay'' about the time a ''VideoGame/WorldOfWarcraft'' 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. [[spoiler:They manage to convert him in the end!!]]
* In the ''Series/MysteryScienceTheater3000'' episode "[[Recap/MysteryScienceTheater3000S05E21SantaClaus Santa Claus]]" Mike Nelson sings "The Devil is a Wiener" to the tune of the soundtrack.
* In ''Series/{{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.
* ''Series/{{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.
* ''Series/{{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 [[SympathyForTheDevil feeling sorry for one of them]].
* On ''Series/GoodEats'' this happens sometimes. Sometimes a BigRedDevil will appear and get his ass kicked by Alton (who at the time was a Christian in RealLife[[note]]A few years after the end of the series, Alton reevaluated his religious beliefs; although not giving up on Christianity entirely, he no longer identifies as a Christian.[[/note]]). 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 [[HereWeGoAgain 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 TropeNamer itself, which is Music/{{Lordi}}'s song ''The Devil Is A Loser''. The song ridicules someone for making a DealWithTheDevil... 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.
** Similarly, many of Carman's songs fit this particular trope as well.
* "The Number of the Beast" by Music/IronMaiden was perceived by some to out the band as Satan worshipers... the song itself plays out like a horror movie (it was inspired by ''Film/DamienOmenII''). 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 Creator/PsychopathicRecords supergroup "Soopa Villainz" has Mr. Diamond ([[Music/InsaneClownPosse Violent J]]) reference this trope in their BoastfulRap "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!"
** From the Music/InsaneClownPosse's "We Like It Like That":
-->"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.
* The song "Beelz" by comedian Stephen Lynch depicts Satan as AffablyEvil and AmbiguouslyGay.
* The Trevor Moore song [[https://www.youtube.com/watch?v=_h8-SBO-RKo 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 ([[MaybeMagicMaybeMundane 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 KirkSummation and sends the devil screaming back to Hell.
--> '''Satan:''' "For all eternity, you will never escape my clutch!"
--> '''Trevor:''' [[ShutUpHannibal "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, [[BreadEggsMilkSquick maybe a little coke]], but if that damns me for eternity then if you ask me the system's broke!"
* "The Devil & Me" by Music/{{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.

[[folder:Mythology and Religion]]
* 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 SeriousBusiness.
* In UsefulNotes/{{Islam}}ic 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 [[{{Fanon}} folk theory]][=/=]AlternativeCharacterInterpretation that ''he and God were once lovers'' kind of odd. Then again, LoveMakesYouCrazy, [[LoveMakesYouDumb Dumb]], and [[LoveMakesYouEvil Evil]]. The idea doesn't appear in religious text and is in fact regarded as heretical. [[BellisariosMaxim 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 UsefulNotes/{{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 [[EarnYourHappyEnding deserving it for trying act ethically over the course of their lifetime]] and all the glory going to God because God enabled it and [[TheChessmaster 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, [[TooDumbToLive 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, [[OmnicidalManiac 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 DealWithTheDevil 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 KarmicTrickster.
** 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 TheProtagonist. 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 [[PityTheKidnapper 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 [[DefiantCaptive 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.

[[folder:Newspaper Comics]]
* Phil, the Prince of Insufficient Light from ''ComicStrip/{{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 ''ComicStrip/TheFarSide'':
--> '''The Devil''': (staring out his home window) Tell me, Margaret... Am I a butthead?
* Swedish comic ''Himmlens Änglar''(Heavens Angels) has Poor, poor Fan(Damn) who is TheWoobie.

* Satan in ''Radio/OldHarrysGame'' is a rather whiny fellow who uses torture and corruption mainly as mechanisms to cope with his own self-hatred.

[[folder:Tabletop Games]]
* The Ebon Dragon from ''TabletopGame/{{Exalted}}'' is basically the [[{{Satan}} Devil-figure]] of the setting; the master of betrayal, lies, and deceit, and the only one of the [[EldritchAbomination Yozis]] who operates on [[CardCarryingVillain standard human morality]]...but see WordOfGod's explanation for exactly why ''his'' villainy is represented not by [[AboveGoodAndEvil alternative]] [[{{Ubermensch}} 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."
* ''TabletopGame/YuGiOh'':
** The Infernoids are something of a meta-example, an archetype of Fiends that look like mechanical devils, [[NamesToRunAwayFromReallyFast 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 [[http://yugioh.wikia.com/wiki/Dante,_Traveler_of_the_Burning_Abyss Dante]] and [[http://yugioh.wikia.com/wiki/Virgil,_Rock_Star_of_the_Burning_Abyss Virgil.]] Without them, the Graveyard activation requirements of their effects is difficult at best.

* 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 UltimateEvil usually is, possibly because he's voiced on the CD by Randy Newman.
* Conor [=McPherson=]'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.

[[folder:Video Games]]
* Demise is presented as a SatanicArchetype in ''VideoGame/TheLegendOfZeldaSkywardSword'', 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 [[TheHero 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 [[spoiler: Ganondorf]], for eternity, but even he has yet to achieve a permanent victory over the two.
* In the ''VideoGame/SamAndMaxBeyondTimeAndSpace'' 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 BigBad, who eventually fires him.
* Satan from ''VideoGame/PuyoPuyo'' and ''Madou Monogatari'' is a pathetic StalkerWithACrush 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.
* ''VideoGame/PonyIsland'': 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 ''VideoGame/{{Catherine}}'', [[spoiler: Catherine's father, the demon Nergal appears when Vincent proposes to his daughter to try to intercede. He's completely harmless, gets [[GroinAttack 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 ''VideoGame/{{Cuphead}}'' ([[NintendoHard and he very much is]]), but at the very last portion of his boss fight, [[spoiler: 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 ''Webcomic/DinosaurComics'' spends all his time talking to T-Rex about video games and internet slang, and he drinks grape juice from concentrate.
%%* The webcomic ''[[http://www.inhislikeness.com In His Likeness]]''.
* ''Webcomic/{{Sinfest}}''
** 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 "[[ScrewySquirrel the Wascally Angels]]", [[http://www.sinfest.net/view.php?date=2009-12-19 pity of Buddha]] and made aware that he's LonelyAtTheTop. The closest thing he had to a friend was his [[spoiler: son]] LoonyFan L'il Evil, a HarmlessVillain whose faith might as well have been HoYay.
** The AntiChrist was so pathetic that he finally got a life only [[AmnesiacDissonance after accidentally mind-wiping himself]] by drinking from Lethe and so far no one (including Devil) wanted his old personality back.
* In ''Webcomic/SluggyFreelance'', 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 ''Webcomic/RoosterTeeth'' Comics, Hell is tech support for Apple, the Devil is the still the Boss, but he wears Khakis.
* In ''Webcomic/DeadDuck'', 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? [[spoiler: ''God'']]
* Inverted in ''Webcomic/HolyBibble''. 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.

[[folder:Web Original]]
* Once faced with Tennyo and Generator in the story "Sit In" in the Literature/WhateleyUniverse, the demon lord (okay, brevet under-baron) Phesclangorenthal rapidly turns into this.
* Discussed by [[Creator/BobChipman Moviebob]], who believes that when you take away all the stories and rumors, the devil is less ComicBook/LexLuthor, and more Starscream.
* In ''WebAnimation/BonusStage'', Satan rambles on about nothing and [[CoolAndUnusualPunishment makes people]] watch ''WesternAnimation/TimeSquad'', watch ''WesternAnimation/{{Shrek 2}}'' or eat his mom's spaghetti. [[spoiler:He also lets Joel, Phil and Elly out of hell.]]
* In later episodes of [[WebVideo/VinesauceTomodachiLife Vinny's Tomodachi Life streams]], Satan ends up moving to Vineland Island. [[AffablyEvil He quickly makes lots of friends]], wears a basketball jersey among other ridiculous outfits, and lives in a brightly-colored apartment. [[LampshadeHanging Vinny freely admits that this is the least threatening version of Satan he's ever seen.]]
* In ''WebVideo/HellsingUltimateAbridged'', Satan (who shows up in Episode 8 when [[spoiler: 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!"

[[folder:Western Animation]]
* [[ExactlyWhatItSaysOnTheTin The Red Guy With No Pants]] from ''WesternAnimation/CowAndChicken'' and ''WesternAnimation/IAmWeasel''. He certainly looks the part but he's only referred to as the devil in the first show's pilot (in which his "EvilPlan" is to make Chicken smoke cigarettes).
* On ''WesternAnimation/SouthPark'', 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 [[VillainDecay hasn't recovered since]]. At times, his demeanor borders on self-sabotaging, making him more of a ''[[TheWoobie woobie]]''. [[spoiler:Then he had enough and killed Saddam.]]
** Amusingly, [[GodKartingWithBeelzebub God Himself called him out on this]]:
-->'''God:''' What the hell happened to you?
-->'''Satan:''' Huh?!
-->'''God:''' You got kicked out of here for being a headstrong rebel. [[TheReasonYouSuckSpeech And now you're a whiny little bitch]].
* The Robot Devil from ''{{WesternAnimation/Futurama}}''. The guy is [[IdiotHero outsmarted by Fry]] and in one episode is seen in jail. [[ManChild He's also whiny]], ScreamsLikeALittleGirl [[ImprobableWeaponUser when you hit him with a fiddle]], [[ArsonMurderAndJaywalking and lives in New Jersey]]. His only positive trait is that he's a good musician.
* In ''WesternAnimation/GodTheDevilAndBob'', The Devil is shown more as an incompetent and effeminate weirdo [[WellDoneSonGuy with creator issues]] than a powerful master of temptation. His evil schemes are often self-defeating but occasionally he proves he's a NotSoHarmlessVillain.
* ''WesternAnimation/JimmyTwoShoes'': 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 SmugSnake HarmlessVillain who is incapable of running things without [[OnlySaneEmployee Heloise]]. He's also a massively LargeHam, because he is voiced by Sean Cullen.
* Played with in ''WesternAnimation/LucyTheDaughterOfTheDevil'': Satan seems like a harmless yuppie right up until the point where he tries to murder you in your dreams with burrowing flesh-worms.
* ''WesternAnimation/ThePowerpuffGirls'' makes this a SubvertedTrope. [[SissyVillain Him]] may mince around [[CreepyCrossdresser in drag]] between launching invariably doomed {{Evil Plan}}s, but he is ''far'' from harmless. An [[CompleteImmortality immortal]] RealityWarper, Him only loses because his schemes hinge on exploiting some character flaw, a MonsterOfTheWeek, or poorly-chosen combat conditions. He comes far closer to success than other villains, and [[BadFuture one particular episode]] [[HellOnEarth demonstrated exactly what would happen]] [[EvilOnlyHasToWinOnce should the girls fail]]...
* In ''WesternAnimation/TheSimpsons'', whether he's a loser or not is a case-by-case basis:
** He's certainly a loser in the [[HalloweenEpisode Treehouse of Horror]] segment "The Devil and Homer Simpson", where his own JuryOfTheDamned 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 ''WesternAnimation/UglyAmericans'', 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 ''WesternAnimation/DarkwingDuck'', 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 ''WesternAnimation/PinkyAndTheBrain'' 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 ''WesternAnimation/RickAndMorty'' episode "Something Ricked This Way Comes" (actually a parody of ''Literature/NeedfulThings'') Summer gets a part-time job at the Needful Things thrift store, which seems to be a lot like it was in the book, [[spoiler:until Rick [[GenreSavvy 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."
* ''WesternAnimation/RockosModernLife'' gives us Peaches, Dark Overlord of [[GoshDangItToHeck Heck]]...who gets bossed around by Heffer's late [[NeverMessWithGranny grandma]] and [[ActuallyThatsMyAssistant isn't]] ''[[ActuallyThatsMyAssistant actually]]'' [[ActuallyThatsMyAssistant the ruler of Heck]].