There is a subtle distinction between Stupid Evil and Chaotic Stupid. Sure, the Chaotic Stupid character is also likely to Kick the Dog. But he's just as likely to Pet the Dog, Shave The Dog, Paint The Dog Purple, or even Ignore The Dog Entirely To Run Off Chasing Butterflies. In short, the 'true' Chaotic Stupid character is the one who thinks that being Chaotic Neutral means being batshit insane. And by "insane", we mean more Gogo Dodo than Hannibal Lecter.
This guy is willing to prove his madness at any time he feels it needs proving, which is all the time. Expect all sorts of "wacky hijinx" from talking in Word Salad to annoying important NPCs (as well as the other players) with stupid jokes. While a little comic relief can be refreshing once in a while, the Chaotic Stupid character takes it to a level which threatens to turn the entire game into a farce, or even gets the other party members killed. Suffice to say, the Chaotic Stupid should never be let within ten feet of any sort of magic, especially the type that can be exploded in the middle of the party for multiple d6s of damage. He's also at a risk of suffering from Chronic Backstabbing Disorder, but it might not be lethal to whoever he betrayed, since he's as likely to kill them as he is to pull down their pants.
Often overlaps with The Loonie, a player archetype from the famed Munchkin Files. Needless to say, several player's handbooks have attempted to disabuse clueless players of the notion that chaos is a blank check to loosen their screws. Though the Second Edition Advanced Dungeons and Dragons Player's Handbook described Chaotic Neutral as the alignment of "lunatics and madmen", even this was not intended to be Chaotic Stupid (although the example Chaotic Neutral party member in the party of all alignments was most definitely Chaotic Stupid, randomly yelling at the top of his lungs and doing a suicidal charge at the dragon and getting roasted). The various incarnations of the Third Edition rules said of the Chaotic Neutral alignment, "Remember that the chaotic neutral character may be unpredictable, but his behavior is not totally random. He is not as likely to jump off a bridge as to cross it." Some people just didn't get the memo, though.
Often an underlying reason to Attack! Attack! Attack! and Leeroy Jenkins. Compare Too Dumb to Live, It Amused Me. For what happens when other alignments are played to a degree it becomes stupid, see Stupid Good, Lawful Stupid, Stupid Evil, and Stupid Neutral.
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Wrath from the 2003 anime adaptation of Fullmetal Alchemist is this due to his utter lack of impulse control or thinking things through. To illustrate, he fused with Trisha Elric's remains to prevent them from being used on his mother surrogate Sloth. After he got done killing Lust, he fuses with Sloth while both her and Ed know what that would do, merging her with the remains and leaving her paralyzed, allowing Ed to finish her off.
While not an Adventure example, Tomo Takino of Azumanga Daioh qualifies as this. For example, the time that she threw the keys to Chiyo's Summer Home into the forest just as Chiyo was about to unlock the door. And thought that it would be funny if she did it a second time.
Bobobo Bo Bo Bobo is utterly incomprehensible even to his own allies. Practically his entire being is driven by Rule of Funny, and he's just as likely to start punching out his own teammates or using them as human shields as he is to lay the smackdown on whatever villain he's fighting.
Chaka in Black Lagoon, from his very introduction seems to be working overtime to get himself killed. Literally everything he does is incredibly stupid, from interrupting a yakuza meeting to talk obnoxiously about nothing, trying to impress Revy, who is working as a bodyguard, by beating the shit out of the guy she's supposed to protect (which he only survives because she didn't have her guns with her), kidnapping the teenage daughter of his yakuza boss with plans to sell her into sex slavery and then just kind of hanging around at a bowling alley for her bodyguard to show up, or killing his remaining gang when Revy and Ginji massacre them. He would be best summed up with "all balls, no brains" but he's too much of a Dirty Coward for even that to be true.
Deadpool is the face of Chaotic Stupid in modern comics Depending on the Writer. He beat the Taskmaster (whose power is an almost supernatural ability to "read", copy, and perfectly perform and understand the muscle movements and fighting styles of his opponent) in hand-to-hand combat by taking a break in their fight to dance and otherwise make himself unpredictable. He even begins his gambit by pushing a female X-men member through a skylight into a indoor pool entirely filled with pancakes. Which were only there in the first place because he just suddenly decided to make a few thousand pancakes when he woke up that day. Then again, this is from the guy who knows he's in a comic book. Maybe he's onto something.
In Yet Again, this is Crypt Oogakari's usual designation, easily being the most insane member of the main cast and the Oogakari family as a whole. The rest of his family fall into the neutral range, and he only joins them during his brief bouts of sanity (at which point he becomes a Blood Knight of the highest caliber).
Hydell in Lockout is chaotic evil, but it is at least partially due to brain damage from being put in stasis.
In the first Highlander film, The Kurgan's joyride-rampage through New York, wherein he drives down the wrong side of the road, singing "New York New York" while playing chicken and running over pedestrians, served no purpose other than a hilarious classic moment in comedy history.
Mark Whitacre in The Informant, who becomes a whistleblower/FBI informant under the guise of doing the right thing when he's actually scheming to take over his company. And he fails in spectacular fashion at both due to his increasingly stupid mistakes.
Frank Begbie of Trainspotting strays into this territory frequently, given that he insists not only on being a violent and often sadistic brawler, but often doing it within plain sight of people who are liable to call the police or remember his face. At one point, after kicking in a man's head and accidentally slicing open Spud's hand, he stands right in front of the bar and various shocked witnesses and demands that Renton take at least a minute to "bring me doon a fukken ciggareh" before even considering leaving — or taking his injured friend to a hospital. He's also been known to attack bystanders for eating chips too loudly. Neutral Axe Crazy might be a better description of his alignment, come to think of it.
The Helmacrons from the Animorphs series. They are extremely tiny, almost microscopic aliens, whose ships are about the size of a hot wheels car, but what they lack in size, they make up for in sheer crazy. They execute all of their leaders, under the premise that if they were alive, they would make mistakes. They still follow their leader's orders though, despite the fact that they are dead. They are also notoriously stupid, and extremely gullible, at one point, allowing Marco to repeatedly mock and insult them to their faces, because he told them in Earth culture, it's considered a form of submission.
Zaphod Beeblebrox in The Hitchhiker's Guide to the Galaxy. He's clearly highly intelligent, but so ridiculously impulsive and attention-seeking that in any situation he could do anything from set off on a quest to discover one of the great secrets of the universe or escaping from prison to go to a disco. A really good example is in The Restaurant at the End of the Universe in which he steals a Cool Spaceship from a rock band he enjoys, even though he has already stolen a much better spaceship anyway, for no real reason. Exploited as his flaky Attention Whore personality makes him the ideal person to become President of the Galaxy, distracting from the people really in control.
Live Action TV
Sam's mother on iCarly: The woman drove her car after getting eye surgery, causing her to crash through a wall at the school. Also, Sam and Melanie were born on a bus because she took one while having labor pains instead of calling a cab.
Worse than the iCarly example, an episode of CSI had a man whose stepdaughter died after ingesting hazardous material because he decided to take the bus to the hospital instead of calling an ambulance. Then, instead of admitting what had happened to the authorities, he left her body outside in a pseudo shrine so it appeared she'd been murdered.
Ziggy Sobotka from The Wire. Lighting hundred dollar bills on fire in a pub full of poor working men, buying a pet duck and giving it whisky, repeatedly picking fights with bigger and tougher people, whipping out his member in a crowded bar - if it's stupid, and he thinks there's a laugh in it, he'll do it. Although he finally wises up when it's too late to do any good.
Reese: This is just wrong! You can make money and please children! This is a senseless act! You are evil! Pure evil!
There was also an episode where he decided to be gentle and kind, but the school descended into anarchy because Reese was the "alpha-jerk" who applied "even-handed bullying". He turned back into his normal self after seeing Stevie (who he declared off-limits because he was in a wheelchair) being bullied, and then administered some justice on the other bully.
The Shadows in Babylon 5 were left by the other First Ones who strike fear and sow discord to show the younger species the benefits of chaos—i.e. freedom, competition, and innovation. They were intentionally set up against the Vorlons of to teach the younger species about the benefits of an ordered society—i.e. to have laws and enforce them. Between them, they were supposed to move the younger species towards a good, harmonious blend somewhere in the middle. But eventually they got too caught up in "winning" the argument, and so the Vorlons became general order-mongers and the Shadows general chaos-mongers.
Jesse Pinkman from Breaking Bad starts out pretty much as the poster boy for this trope, for all he's not exactly thick. Just really impulsive. He actually starts to wise up as the costs keep getting steeper and Character Development hits him like a freight train. Badger, however... nope: Chaotic Stupid all the way. Well, Chaotic Clueless would be a better description in his case, really.
The Dragonlance setting of D&D had the Kender, who were halflings with an unique blend of fearlessness and a habit of kleptomania "borrowing things", which made them the perfect excuse for Chaotic Stupid behavior in the wrong hands (so much that they were frequently considered The Scrappy of the setting).
Planescape basically had an entire faction based around this trope. The Xaositects believed that the universe had no inherent order to it, and that truth could be found only in chaos. Naturally, this meant speaking in Word Salad and generally acting like lunatics as much as possible. This is how they're described in the sourcebooks, so it's NOT just players taking things too far in this case.
There were a few Xaositects who seemed somewhat lucid. One sourcebook mentioned The Painter, an artist in the faction who started to paint because, well, she decided she really wanted to paint. And she was quite good at it, so much that her work made her somewhat of a celebrity in Sigil.
And the Slaadi, who are literally Chaotic Neutral (and consequently Chaotic Stupid) personified.
"He said he was looking for the Happy Hunting Grounds. I didn't know what he was talking about... so I ate him."
In fact, 4th edition gave Slaadi the official alignment of Chaotic Evil (they were traditionally Chaotic Neutral) because they are so Chaotic Stupid that they want to tear down all of the rules everywhere... Including the rules that keep the very fabric of existence functioning. For the Lulz.
Of course, Slaadi can be presented as "opposed to all law" without being "opposed to all sanity"... but Rule of Funny has its place in these games.
Vampire: The Masquerade GMs sometimes have to deal with "fishmalks", Malkavian characters who think madness and extreme loopiness are synonymous (the name comes from being the sort of people who would presumably slap the Prince across the face with a fish for the lulz). That's bad enough, but during the second edition White Wolf produced a downloadable sample adventure that took this to an extreme, replacing the usual Malkavian derangement with something vaguely resembling a seizure played for laughs.
A good part of why Chaos hasn't yet conquered the galaxy in Warhammer 40,000 is because of this, the four main gods simply hate one another too much to allow alliances to continue very long.
Tzeentch may or may not be actively preventing a solid Chaos victory with his plots, because Victory Is Boring.
It's not just because victory is boring, but because Chaos is inherently self-destructive. Tzeetch in particular is the god of ambition and scheming, and if he ever actually reached his ultimate goal (whatever that might be), he'd disappear in a puff of logic, as scheming is part of his very nature.
KhârntheBetrayer (what a guy!) single-handedly destroyed his entire Legion's organization when fighting the Emperor's Children on the bitterly cold planet of Skallathrax. When the other World Eaters were actually stopping the assault to take shelter, he ran around with a flamethrower burning down the shelters, other World Eaters, and occasional Emperor's Children. Ever since, the World Eaters have been reduced to eight-man sellsword warbands. For his actions, Khârn was made Khorne's champion, resurrected whenever he dies and immune to all forms of psychic powers. In fanon, he actually does more damage to his own side (by planting melta bombs on transports, playing commissar or throw-the-cultist) than the enemy does.
In Ciaphas Cain (HERO OF THE IMPERIUM!), Khornate berserkers once tried to screw up a Slaaneshi summoning ritual that would have caused the planet to fall to Chaos, simply because their two gods are opposed.
Orks could take over the galaxy, but haven't because they like fighting each other just as much as they do anybody else. That their entire society runs on Klingon Promotion also helps.
It's been implied in more recent codexes that the Orks are a race of Living Weapons created by the Old Ones to battle the Necrons; though the War is over and their creators are gone, the Orks are still following their biological programming, unfortunately for the galaxy as a whole.
The Donjon De Naheulbeuk RPG has a counter to this behavior (and any other stupid alignment-related behavior) in the form of "Loser points": the GM can give one to the party at any time if he/she feels his players are turning the game to a farce. Gain enough points and bad things happen to the whole party, such as getting their legs broken by mob enforcers or waking up in the middle of a field with two armies charging them.
BattleTech has Clan Ice Hellion, the clan is ever reckless to pick a fight with anyone, especially their fellow clans. They thought that they could conquer Terra on their own, by attacking Clan Jade Falcons occupation zone. To put it in perspective, the Hellions like employing light and medium mechs as their main strike force, against other clans who like fielding larger and heavily armed omnimechs.
Sheogorath, of The Elder Scrolls video game series, and his antics fall pretty squarely in Chaotic Stupid territory. He's not called the Mad-god for nothing. In one of the expansions it's revealed that he even moonlights as his own Lawful Stupid archnemesis — or, more accurately, that Jyggalag, Daedric Prince of Order, was cursed back in the day to become the relatively ineffectual Sheogorath, Prince of Madness.
In Morrowind, he had rather less of this, giving the impression not that he himself was mad (at least not to Cloud Cuckoo Lander levels, though he may have been slightly cracked), but that it amused him to drive mortals crazy and observe the results. His voice acting is the most "normal" of all the Daedra lords in the game, his image simply a distinguished gentleman. From Oblivion onwards, Chaotic Stupid is in full force.
To a lesser extent, you have Sanguine, Daedric Prince of debauchery, who at one point sends the Dragonborn on a drunken rampage through half the country because it'd be funny. Of course, it kind of was, but when you practically personify the trope 'What Did I Do Last Night?', Chaotic Stupid is there in full force.
The Umgah from Star Control are an entire ALIEN RACE of this trope, having genetically engineered themselves to the point of insanity. Their idea of 'funny pranks' involve invoking wars between evil spiders and hippy bird people, making a powerful psychic lifeform sentient once more so they can see if it will do tricks for them, dropping planetoids into the oceans of inhabited planets, and scaring the crap out of an easily scared race of mollusk things. Over the course of one conversation, you liberate them from the aforementioned powerful psychic lifeform and get named their "Great Hero," they give you ships, and then they decide that "Great Hero" is boring, name you "Great Enemy" instead, and declare war on you.
They then attack you with an infinite wave of ships, which you can attempt to combat with the identical ships they just gave you. They probably think this is hilarious.
The Thraddash might qualify as this, too. They are a parody of typical warrior races who revel in combat so much that they have nuked themselves back to the stone-age eighteen times. They are on their nineteenth attempt at having a civilization by the time you meet them, and can still be easily goaded into attacking more powerful races simply because you suggest it to them. Alternately, they can be goaded into emulating The Three Stooges.
Their greatest invention to date appears to be the Reeunk Afterburner, named after its accidental creator. Reeunk was a mechanic who thought it was a fine idea to put a lit cigar into a starship's aft fuel valve. And yes, he was burned to a crisp.
While nearly every Touhou character is Chaotic Neutral, they tend to avoid this trope (or at least Reimu reminds them to behave). Fairies however are both dirt stupid (Cirno is actually the smartest fairy yet encountered) and highly unpredictable, due to both their incredibly short lifespans (at least in comparison to other types of youkai) and ability to immediately ressurect after death or serious injury, creating decidedly warped views of mortality. As noted in Perfect Memento in Strictest Sense their most reliable behaviour is playing pranks, but even then they range between getting people lost or stealing their food to pushing them off of a cliff or setting them on fire, and tend not to differentiate between a powerless human and a centuries-old being with enough power to effortlessly disintegrate them.
In the roguelikeDungeon Crawl, there's the god Xom. Whereas other gods have a piety level based on your actions (good gods appreciate destroying undead, for example, and evil gods killing living beings), Xom's piety level is entirely random. As a worshipper of Xom, you are considered his "plaything" (if piety level is low) or "toy" (if high), and he grants you gifts such as teleporting you randomly at will, summoning dozens of butterflies, or gifts of anything; anything from powerful items (especially ones that your character isn't any good at using) to plain rocks.
Mortal Kombat Deception introduced an entire race and realm of chaos, filled with people who sometimes speak backwards, play games like Everybody Runs Around, and, when asked a yes or no question, respond with "Yes, no, yes, no, yes, no, yes." The only named member of the Chaosrelmers is Havik, the Cleric of Chaos, who will fight for anyone regardless of alignment if they will bring chaos. He even gets a Lawful Stupid nemesis in Hotaru. The citizens also greet you and thank you for running up and punching them.
Dawn of War: When exiting a transport, Khornate Berserkers will proudly proclaim that they need a new driver, as this one's dead.
Every AI-controlled character in The You Testament thanks to a fantastic example of Artificial Stupidity that basically makes everyone act completely at random, with a leaning towards needless Jerkassery. Characters will randomly wander the map, sit down in the middle of nowhere, get up, pick up an item, drop the item, run up to someone else, hug them, and then suddenly beat the piss out of them for no good reason before going up to you and stealing whatever it is you're holding (and if you try to take it back, they'll claim it's their's and threaten you.) Emptying your mind meter will also make the player character go insane and act just like the others.
Elan from The Order of the Stick, despite being the page picture, isn't quite an example of this. He can often be stupid (less so as the comic goes on), but it's not inherently related to him being Chaotic, it's just part of who he is. The page picture makes sense when you realize that Elan trusts Haley implicitly and Haley had just snapped at Elan that, as a party of player characters, everything they do is technically an adventure. Elan being Elan took this literally.note Bonus points for Lawful Stupid Miko coming upon the scene.
Rayne from Least I Could Do has been drifting into this alignment since 2004, and is now merrily swimming within it, his actions are almost totally random and utterly incomprehensible to the outside observer, so much so that people barely notice anymore unless his zany antics directly impact on them, which they usually do
In a Knights of the Dinner Table strip, the characters run afoul of the god Thor; when Thor appears to avenge the insults to his name (guess who insulted him), Bob and Dave and Brian immediately start attacking him despite BA (the Game Master) pointing out that Thor is impervious to all mortal weapons, has infinite hitpoints, etc. Sara immediately has her character run away, and convinces Brian to have his character do the same. Bob's and Dave's character die shortly afterwards, with Bob and Dave bitterly complaining that they don't understand why.
Ben, of the KOTD spin-off/homage Fuzzy Knights, lives and breathes Chaotic Stupid (and is even called that in-strip once), not just in the characters he plays but to a large degree outside the game. When Target and Violet try his impulsive play style for a night or when Target switches his character to Chaotic Neutral, stuff gets interesting.
In one of the Deep-Immersion Gaming sequences in Something Positive, Mike is apparently playing a character like this. Jason refers to him as "Mr I Can Shoot Guards Who Are Using The Bathroom But It's Wrong To Desecrate The Dead", and Mike protests that he bases his character's morality on coin flips.
Emily in Questionable Content, whether she's swimming and chanting "Muskrat, Muskrat, Muskrat" or punching a robot because she thinks his head looks soft and is then surprised her hand hurts, her Cloudcukoolanderness puts Hannelore's to shame.
Some players in Survival of the Fittest attack everything in sight no matter what it is, and disregard whether they can even win the fight or if they'll benefit more from an alliance or at least not picking a fight.
122. The paladin's alignment is not Lawful Anal. 651. My alignment is not Sarcastic Good. 742. Apparently Chaotic Angry and Neutral Hungry aren't real alignments either. 863. Even if there is no alignment in Traveller, giving feuding TL1 tribes TL12 weapons and putting the results on PPV is just wrong. 1059. Even if the villain is Lawful Evil, slapping a cease and desist order on him isn't going to work. 1949. Can't free the hostage with a surprise game of Red Rover. 2172. Even if its beneficial, no changing the number of limbs on a character without the other player's consent. * Also known as "Psychotic Neutral".
Everyone in The Binder of Shame. "We're Chaotic Neutral, that's practically a get-out-of-plot-developments-free card!" Blobert Smith has a particular tendency to this, his roleplaying described as being like a cross between regular gaming and performance art. Some of the other players come across this way in their real-life personae.
Tednugent, the long-suffering protagonist of Interactive Fiction Fanfic Parody You Awaken In Razor Hill is repeatedly forced into this trope and this sort of behavior, as a character whose actions were controlled by the whims of the readers of the story. Many of them - MANY of them - chose to Command Ted to do outright moronic things regardless of the severity of any given situation he was in - such as Commanding him to challenge the story's Big Bad,Pyramid Hogger to a 'yo momma' contest, or licking things that ought not to be licked. This led to a small Writer Revolt when the 'Narrator' (the author of the story) began to respond to the more ridiculously self-destructive commands with some fairly brutal consequences.
MS Paint Adventures is known to feature shenanigans of this sort. They were quite prevalent during Problem Sleuth, when the comment boxes were open and everything was explicitly coming from player suggestions; sometimes, if the characters really insisted on being engaged in something productive, the players would bid the character continue with what they were doing, but in a sillier manner. Homestuck had a few really good ones early on, before Hussie locked the suggestion boxes, but here and there you still get someone being a bit of a dipshit.
Spoiler Warning's Reginald Cuftbert character combines this and Crazy Awesome and has been know for such feats as taking on a group of Mad Bombers wearing just a bonnet and tuxedo, killing people by rigging the room with C4 and detonating it with himself still inside, stealing weapons directly in front of somebody then selling them back, and managing to stealthily blow somebody up in the middle of a crowded casino without anyone noticing.
Anonymous, if you buy into the idea of Anonymous as an organization. Since it's really just a bunch of random people, some of whom will occasionally join together to enact some kind of wacky (or not-so wacky) scheme, the "organization" really falls under this.
Kim Possible's Shego, when she gets excited about destroying the world, descends into this in "Car Alarm".
Blitzwing's Random face usually falls in this category as well.
The eponymous character of Invader Zim has repeatedly shown himself to be determined enough to not only easily conquer Earth but the entire galaxy, yet his impetuous nature and his COMPLETE lack of consideration for the consequences of his actions results in utter failure and/or the deaths of people he WASN'T trying to kill. Perhaps the best example of this is in the incomplete episode "The Trial", showing that Zim invented an Infinite Energy Absorbing Monster solely to impress his superiors which does exactly what it would be expected to do, killing Zim's fellow scientists and even one of the Irken leaders.
He also killed her counter part not long after, then most of the Irken armada...
And we all remember what happened with the FIRST "Operation: Impending Doom"...
That's disputable, he does want to take over the tri-state area through conquering means, that's pretty evil, he's more Stupid Evil than Evil Stupid... and really Chaotic Evil would be a better description. Like Doctor Two-Brains from WordGirl, he has evil plans, but a chaotic view of how to attain them, and a chaotic limited view of what he wants to attain.
Roger from American Dad! is so obsessed with creating alternate personalities with his infinite supply of wigs and costumes, that he goes out of his way to make sure that some of his personalities are just straight up crazy. For example, a Native American firefighter-slash-serial rapist.
Roger has gradually become more Chaotic Evil as time goes by though. Like murdering Haley's new boyfriend for witnessing overhearing Roger confessing to accidentally killing his new wife.