Laughably Evil



""He's an absolutely awful human being. The strange thing about comedy is that if an awful character makes people laugh, people feel affectionate towards him. It's insane because if they had to sit next to him for five minutes at a dinner, they would absolutely not be able to cope with him. They would loathe him. But because he makes them laugh, they think, deep down, he's alright.""

- John Cleese

Villains can be many things... Magnificent Bastard, horrific, philosophical... but special attention goes to the villain that makes you laugh. It might be because he's an idiot, it might be that you empathize with him, or it might be simply that his actions are so unexpected. In any case, some villains will always be funny.

Of course, funny does not always equal weak. Praise be to the villain who can cause a chuckle from his audience, right before viciously thwarting the hero's best efforts. In fact, if done correctly, the very things that make a villain Laughably Evil can make them downright disturbing once they begin crossing the Moral Event Horizon. Villain laughing at faking someone out with a gun with a "BANG!" flag coming out? Funny. Same villain doing the exact same laugh when shooting them for real a few seconds later? Creepy. A truly well written one can manage to pull off both at once. See the trope picture for an excellent example of this subtype. Just because a character is Laughably Evil, it does not disqualify them from being a Complete Monster and there are many villains that manage to be both. In these cases, what makes them funny also makes them very unsettling because of how much fun they have committing the most horrific acts possible.

Often overlaps with the Harmless Villain (Harmless Villains are inherently funny, but funny villains are not inherently harmless), Affably Evil (get the joke?), Faux Affably Evil (who are often funny), the Ineffectual Sympathetic Villain and Magnificent Bastard. And with Large Ham (playing a villain seems to be very fun). It's also a prerequisite for the Terrible Trio and the Quirky Miniboss Squad. Contrast with Monster Clown, because clowns make people cry. Interestingly, this either subverts or complements Evil Has a Bad Sense of Humor, as does Too Funny to Be Evil, a closely related sister trope. Tends to be the sort who Crosses the Line Twice. See also: Laugh with Me and Beware the Silly Ones.

Anime and Manga

 * Jason Beck from The Big O. When he's not being an egotistical fop, he's actually frighteningly competent. Too bad this is overshadowed by his over the top hubris, which pushes him firmly into the "Laughably" part of this trope.
 * Most of the villains of early Dragon Ball are like this. Such villains include General Blue, who is utterly hilarious in personality but also a very deadly opponent, and Emperor Pilaf, who has no idea what he's doing. Also Majin Buu, especially in his Fat Buu form, where his antics and are so childish, goofy, and cartoonish that you almost forget that his "games" are killing millions of people, at least until the Establishing Shot of the barren wasteland where a thriving city used to be.
 * The Team Rocket trio from Pokémon are this, which is the reason why they are so popular. At least until Best Wishes, when their boss gives them an actual serious assignment.
 * Tobi from Naruto was this at first..
 * Dedede in Kirby of the Stars. He's arguably more evil than his game counterpart, but also one of the most entertaining characters on the show.
 * A number of villains from One Piece, such as Buggy the Clown, a Villainous Harlequin who's (violently) sensitive about his nose, and Spandam, who alternately kicks the dog in new and horrible ways and makes himself look like an idiot.
 * On the opposite side of the power spectrum is Kaku. The second most powerful member of Cipher Pol 9, he can transform into a giraffe. No, you didn't misread that. He can transform into an actual giraffe. Even better, he can transform into a half-man/half-giraffe. One that keeps his trademark square nose. He sincerely believes giraffes to be powerful creatures and during his fight with Zoro was prone to defending them by saying such things as "Witness the power of a giraffe!". Though that could be part-denial since everyone keeps mocking him for his powers. Oh, and he uses his nose as a weapon.
 * Believe it or not, out of all the animals characters can transform into so far, the giraffe appears to be one of the very best (in this form his storm kick attack was amplified like crazy, he can shorten his neck to lengthten his arms and legs, he can shoot out his head like a cannonball ...). The only one that seems to be superior is the rare phoenix.
 * Any animal that can kick a full-grown lion ass-over-appetite is powerful, even if their goofy build and lack of vocalizations in the range of human hearing obscures that fact.
 * What makes the fight even funnier is that Kaku has just eaten his Devil Fruit, and is figuring its powers out as he goes along. Crowning Moment of Funny comes when he discovers the aforementioned "shorten neck to extend arms and legs" move, reasons that it works on the same principle as a pasta machine, then names the move "Pasta Machine." Also in his favor is that, despite being a government agent, he's a pretty chill guy, even giving a good-natured laugh to a post-battle quip from one of the heroes.
 * Mara from Ah! My Goddess. She takes time out of her busy day tormenting goddesses and attempting world conquest in order to knock a child's ice cream cone out of his hands to fulfill a snide wish by his sister. Either Kick the Dog, Crowning Moment of Awesome, or both. A truly admirable commitment to evil on any scale. For those who are wondering this happens in the first season of the TV series—if not in Mara's first episode, then in her first or second appearance after that. The scene in question actually makes her seem oddly like a Disgaea character, laughing maniacally at her "evil deed" and resulting in both of the kids kicking her in the shin simultaneously and high-tailing it, to her angry surprise.
 * Baki and Minki from Hell Teacher Nube. They're (nominally) evil, powerful, hugely destructive Oni, but the former adores ice cream, toys, and riding around on the little kids' train in the park, and the latter has some bizarre notions of what a good big brother/little sister relationship should be like.
 * Gates of Full Metal Panic!: The Second Raid is so over-the-top with his Chaotic Evil antics that everything he does is completely random. Despite the sadistic violence, this makes him even funnier.
 * Wester from Fresh Pretty Cure.
 * Xellos from Slayers might fit...his antics are certainly funny enough; it's just that no one is sure what his real goals are, so calling him a 'villain' may or may not be accurate.
 * He's The Dragon for one of the 2 remaining demon lords. He might be a Draco in Leather Pants, but his efforts always serve his Mistress.
 * Oda Nobunaga from the Sengoku Basara anime. It's not because he's dumb. Or incompetent. Or even snarky, for that matter. It's just that he's so mind-bogglingly, skull-stompingly, baby-eatingly evil that he becomes hilariously awesome just through his very existence.
 * The various teens of Ranma ½ could conceivably come off as this, as opposed to Comedic Sociopathy. Not one of them (except for Kasumi, and even she made mischief on some occasions in the early manga) has done something that doesn't make them look at least partially villainous, yet these same deeds (and the regulars who generally are villains) still manage to be funny because of their attempts at evil.
 * Prince Walter from The Brave Of Gold Goldran fits this trope.
 * Almost all of the Order of the Glittering Star from Star Driver. Their everyday personas are so over the top that you can't fully take their villain sides seriously - all of them being hammy certainly helps too.
 * Katsuhiko Jinnai from El Hazard the Magnificent World is constantly over-the-top and has a funny Evil Laugh.
 * Pixy Misa from Pretty Sammy. She is a parody of Dark Magical Girl.
 * The Golden Witch Beatrice in Umineko no Naku Koro ni is aware that she is the villain of the series, and is just adoring the role. She's a Large Ham and she loves to chew the scenery, just listen to it when she talks to Battler. However, Eva-Beatrice on the other hand...
 * Blastmon from Digimon Xros Wars is said to be immensely powerful, but has the mind of a 5-year-old and calls the other generals by nicknames. Then he's defeated by the heroes and is reduced to a hopping head for the rest of the series. Before him, there was Etemon, an over the top rockstar monkey who's both silly, and far stronger then the last Big Bad.
 * Prince Eccentro of Mon Colle Knights. He's the comedian of the anime, often accompanied by a Fiery Redhead and a Cloudcuckoolander as two of his followers, thus why he's so popular with fans of the show.
 * The aforementioned Batch and Gluko are also quite comedic. Quite often at the end of many episodes, Gluko often happily stands by and adores the scenery while Batch and Eccentro get rather embarassing moments. They even get into rather comedic situations involving Ms. Loon.
 * Laharl in Makai Senki Disgaea has quite the reputation for having some rather funny moments. Also, in Episode 3, Vulcanus becomes this when he accidentally almost falls off a statue and causes it to fall, which leads to Flonne and Etna's clothing & personality swaps. When he finds Flonne sleeping with Laharl and Etna, he flips out and hits her with a This Is Unforgivable! and attempts to kill all three but accidentally falls into a clam exhibit and is unable to get out for the rest of the episode. Later, while he's still trying to get out, he knocks over the same statue again, causing clothing swaps again, this time for Laharl, Etna, Flonne, and one of the Prinnies.
 * Barry the Chopper of Fullmetal Alchemist is an unrepentant Serial Killer whose lunacy and total inability to understand normal human morality is Played for Laughs. Some people view Envy as this, though that has more to do with its terrible fighting skills and godawful fashion sense than with any real humour on its part.
 * Before he went all One-Winged Angel, Father had a tendency to make small, sardonic quips while horrendous battle raged all around him - usually along the lines of "Why does everybody feel the need to demolish my home?"

Comic Books
"Paul Dini on the Joker: Joker's that perfect combination of schoolyard bully and class clown. The kind of sicko who will make you laugh just before he sticks the knife in and twists it."
 * The Joker thrives on this trope. One of the main goals towards portraying the character is to make his actions such that you can laugh one moment, and be horrified the next. Brilliantly brought out by many of the actors to portray him in other media, most prominently Jack Nicholson, Mark Hamill, Heath Ledger and, most recently, Brent Spinner. Whether it's electrocuting a gangster while singing showtunes, casually (and cheerfully) stalking an everyday accountant in the middle of rush-hour traffic, or doing a magic trick by making a pencil disappear, you can always find it either way with the Joker. Cesar Romero too. Maybe it's because he was so Harmless Villain or such a Large Ham, or maybe just because the show was So Bad It's Good, but he was genuinely hilarious, if not nearly as terrifying as Ledger's Joker.

""Moving WALKway! Not moving STANDway, Granny Fuckwit, MOVING FUCKING WALKWAY!!!" (cue gunfire)"
 * What kind of schoolyard bully stabs people?
 * Part of what makes the Joker so terrifying is his special mixture of being funny as all get out but a Complete Monster in many a canon. While other villains have managed to pull off this combination, the Joker is probably one of the best examples in fiction.
 * Speaking of the Joker, don't forget everyone's favorite Villainous Harlequin Canon Immigrant, Harley Quinn.
 * Marvel Comics' Madcap, a Chaotic Neutral who acts deliberately silly, and whose power is simply to make people act uninhibited.
 * Herr Starr from the Preacher (Comic Book). Every time he shows up he has a smartass line, but his Crowning Moment of Funny was when he scares the shit out of some poor old lady for blocking the moving walkway by shooting wildly at her.


 * By this point in the series he's had to deal with "an angel, a whore, an eunuch, several dozen idiots, an unkillable mick, a one-man holocaust in a duster coat, the occasional twenty-course banquet for the mother of all fat fuckers, inbreeding, family feuds, bulimia, a retarded child (always good for a laugh), and the utter destruction of our most sacred shrine and secret retreat in the detonation of a fifty-ton bomb." Not to mention "having my head carved into a giant gleaming dong", so it's understandable that he'd be a mite testy.
 * Superboy-Prime, with his wonderful bits of dialogue such as "I'll kill you! I'll kill you to death!"
 * Larfleeze of the Green Lantern books is the Daffy Duck of the DCU.
 * Jameson is a power-hungry undead Mad Scientist and demonologist. He's also the Meta Guy of Creature Tech, and as such spends most of his time making awful puns, references to other media, Chewing the Scenery, Getting Crap Past the Radar, and hanging lampshades anywhere they'll fit.

Fan Fics

 * from the Tamers Forever Series. While he's not technically evil there's no denying that he's one of the most ruthless and hilarious characters in the series.

Film -- Animated
"Elastigirl? You married Elastigirl? (notices the children) And got bizzaaaay!"
 * The Thief and the Cobbler: Zigzag, the Evil Chancellor, is usually amusing, but is introduced by a scene where he condemns a cobbler to death for spilling tacks he happened to step on, and only gets worse.
 * The Disney Animated Canon provides us lots of Laughably Evil villains:
 * Peter Pan: Captain Hook. That is all.
 * No one makes you laugh like Gaston.
 * Kronk from The Emperors New Groove. Even though he's not all that much of a villain to begin with...
 * Yzma is so over the top in her characterization and frequent Lampshading of standard Disney villain tropes that she's somewhere between this trope played straight and a parody of it. It also doesn't hurt that the character is voiced by Eartha Kitt.
 * In The Incredibles, Syndrome is another Disney villain who is both humorous and unnerving. Many of his lines will sound very familiar to anyone who is a comicbook fanboy or knows one, and his goofy, hammy demeanour can almost make you forget that the guy is guilty of mass murder, would knowingly kill children, and is essentially plotting to start killing hundreds of innocent people and get hero-worshipped for stopping. Just as an example:

"Hades: Er, guys? Olympus would be that way..."
 * Hades from Disney's Hercules. Thanks to James Woods, he changed from being a stereotypical chilling villain to fast-talking, tempestuous and absolutely awesome. Easily the best part of the movie.


 * He manages to carry on this trait to the TV series, and to video games... any Kingdom Hearts cutscene featuring Hades are generally hilarious.
 * Apart from the examples above, there's also Kaa from The Jungle Book, Pete, any villain in The Rescuers films, Edgar from The Aristocats, and Sid from Toy Story, to name a few.
 * The hyenas from The Lion King.
 * Baron Ruber of Quest for Camelot twitches, talks to himself, and does silly little dances during his Villain Song.

Film -- Live Action
"Guy of Gisborne: Why a spoon, cousin? Why not an axe, or... Sherriff of Nottingham: Because it's dull, you twit. It'll HURT. MORE."
 * Alan Rickman as the Sheriff of Nottingham in Robin Hood: Prince of Thieves


 * Austin Powers: Dr. Evil, Number Two, Frau Farbissina and the rest of the gang.
 * The Green Goblin was partially one of these in the first Spider-Man movie, mostly because the character itself is supposed to be that way, but also because he was so hammy.
 * In Extremities, the rapist gets all the funny lines.
 * Any film that's So Bad It's Good. Particular examples are The Phantom of Krankor, Kobras, Torgo and The Master, Eros, and CrEEEEEdence Leeeeonorrre Gieeeellllgud.
 * Adenoid Hynkel from Charlie Chaplin's The Great Dictator. He is portrayed as infantile and crazy from power. Some consider this version of reality to be too humorous.
 * Ray "Bones" Barboni in Get Shorty. He can spin on a dime between being menacingly brutal, intentionally funny, and humorously incompetent. In one scene, he beats a character half to death and almost gets his balls blown off in the process. When Dennis Farina plays villains, they are usually both funny and nasty at the same time.
 * Not sure if that was intentional, but Komodo of Warriors of Virtue IS the missing Looney Tunes.
 * Tuco in The Good the Bad And The Ugly - it's debatable whether he's actually evil, because some consider him the most sympathetic and relatable character in the film, but he's far from a good guy and is absolutely hilarious.
 * The villain of the CarrotTop comedy Chairman of the Board is the only particularly funny thing about it. It isn't worth it.
 * Biff Tannen (and his relatives) from the Back to The Future trilogy.
 * Freddy Krueger in A Nightmare on Elm Street sequels. Which is quite a feat from a rapist child-killer.
 * Not exactly evil, but the title characters in The Usual Suspects have an empathic moment where they spontaneously burst out laughing in a police line-up—in fact, director Bryan Singer lampshades this in an interview by saying that there's a certain humanity in a bunch of guys getting along and laughing together, even if they're horrible criminals. (The reality is that the actors themselves just couldn't get through the scene without breaking character and cracking up.)
 * Duamerthrax in the Dead Gentlemen's Demon Hunter movies. The films as a whole are pretty goofy.
 * The Octopus in Frank Miller's The Spirit. Gems include the line "I'm gonna kill you all kinds of dead!" and accidentally making a clone that was only a head and a foot.
 * Pam Ferris as The Trunchbull in Matilda. While still managing to keep the character scary, no less.

Literature

 * The title devil from The Screwtape Letters, who has no sense of humor himself. Lampshaded at one point where he complains that the girl the Patient is falling in love with is "the sort who would find me funny."
 * The Ciaphas Cain series tends to draw from this trope for its humor, only instead of the source being an individual villian, it is the Grimdark nature of the Warhammer 40,000 setting itself that provides the source.

Live Action TV
"As Victim: Oh, how can I thank you, you mysterious black-clad hunk of a night thing? As Angel: No need, little lady, your tears of gratitude are enough for me. You see I was once a badass vampire, but love, and a pesky curse defanged me, and now I'm just a biiiiiig, fluffy puppy with bad teeth. As Victim: But there must be some way I can... show my appreciation. As Angel: No! Helping those in need's my job, and working up a load of sexual tension and prancing away like a magnificent poof is truly thanks enough. As Victim: I understand. I have a nephew who's gay, so- As Angel: Say no more. Evil's still afoot. And I'm almost out of that nancy-boy hair-gel I like so much. Quickly, to the Angel-mobile! Away!"
 * John Simm's Master in Doctor Who certainly qualifies as a Crosses The Line Twice villain.
 * Benjamin Linus is one ruthless, manipulative, and downright creepy motherfucker. He also has some of the best lines in the series.
 * All of the villains in the Adam West Batman show fit, but the best examples are all of the one-shot villains that are unique to the show. And the Riddler, whose infamous riddles would continuously be solved by a Boy Wonder who was otherwise only good for getting kidnapped.
 * All of the villains on The League of Gentlemen. There are very few shows that could make a pair of incestuous Corrupt Hick Serial Killers hilarious.
 * Spike could be quite funny, such as when he passed out in Angel's backyard and woke up when the sun made his hand catch fire.
 * Also in the episode where he watches from a roof-top while Angel saves a girl and provides sarcastic voice-over narration.


 * Angelus is even funny sometimes, in a sick sort of way. ("Othello and Desdemona! My favorite couple. Only Desdemona didn't love the other guy.")
 * Glory is the Alpha Bitch with apocalyptic plans.
 * The Trio start out as a mix between this and Harmless Villain.
 * Like Kefka and The Joker, Alpha from Dollhouse can make you laugh and cross the Moral Event Horizon at the same time.
 * The Trickster always manages to deliver some sick and twisted poetic justice in a way that will make you laugh—maybe because it's completely ridiculous, extremely clever, or just Actually Pretty Funny.
 * Lord Fear in Knightmare was a hilariously snarky villain.
 * Yogostein, Kitaneidas, and Kegalesia in Engine Sentai Go-onger.
 * Oiles Gils is an Adult Child General Failure who throws tantrum and gets into hijinx that makes him the butt of jokes and generally act like a Spoiled Brat. He still has some nasty tendencies of plots that makes even his more serious Dragon horrified enough.
 * The Power Rangers franchise has a lot of these guys, really - ranging from Squatt and Baboo the Tagalong Kid monster henchmen of Rita Repulsa to Flit the Fly Crazy Combat Commentator.

Musical

 * Monsieur (and also Madame) Thénardier in the musical version of Les Misérables, quite an achievement considering how nasty he is in the book. Monsieur Thénardier's Villain Song "Master of the House", in which he swindles guests out of money and possessions, stands out as a rare moment of light relief and is probably the funniest song in the entire play.
 * Similarly, Fagin in Oliver!

Professional Wrestling

 * Chris Jericho was one of these in WCW and in his early days in WWE. When he returned to the WWE, he tried to be a face, but has since lapsed back into this, and is much better.

Tabletop Games

 * Da Orkz of Warhammer 40000 are a race of Psychopathic Manchildren who fill in as the comic relief of the setting, in no small part due to crossing the line twice. Most factions in Warhammer 40k will wage genocidal war on you because they hate you with the burning fire of a thousand suns. The Orks will wage genocidal war on you because it's their idea of entertainment.
 * Since 40K is in many ways Warhammer Fantasy Battle IN SPACE!, the Orcs and Ogres in Warhammer Fantasy have similar traits.
 * In Nomine features Kobal, the Demon Prince of Dark Humor. There is also his "blood brother" Haagenti, the Demon Prince of Gluttony, who also holds purview over torture and sight gags (which many consider to be a form of torture).
 * Pathfinder goblins, bless their psychopathic little hearts.
 * Goblins in any given Magic the Gathering setting tend to be psychopathic, destructive, homicidal, genocidal, suicidal and absolutely hilarious.

Video Games
"Bowser: I'm HUUUUUUUUGE!!!!"
 * Edwin from Baldurs Gate and its sequel is sociopathic, irritable and has a massive ego but is genuinely cranky to the point of amusement and bumbling enough to be this trope. Half the laughter comes from him being sulky.
 * Many, if not all, of the main enemies in the Super Mario Bros. series. From Bowser's kidnapping of the princess turning out to be lovesickness, Wart being the tyrant of a dream world while critically weak to vegetables (he hates the taste), to even the names of many of the stage bosses (King Caliente's Spicy Return!). Not to mention anyone who's an antagonist in an RPG or spinoff (*Chunks Awaaaay!* ) (I HAVE FURY!).
 * Special mention also goes to Dimentio, who often has rather quirky behaviors that count as somewhat comical, and yet commits genuinely horrific actions while cracking jokes.
 * However, Bowser is portrayed in a more serious manner in the main series platform games. Especially Super Mario 64 and Super Mario Galaxy.
 * He's a more serious threat in terms of malice in said games, but is still a comical ham of the highest order personality wise, so fits this trope to a tee.

"Hero: (after Escherion turns into a frog) Huh... I guess you inverted your powers. Every spell you try to cast on me, you actually cast on yourself. Escherion: *ribbit ribbit* Hero: I'm sure you just said something very rude in froggy."
 * Let's not get started on Bowser in Mario Party. Especially in 7, where he'll take a picture of the characters and make you pay for it.
 * Jester from Devil May Cry 3 is funny as Hell.
 * Kefka, a rare example of a villain who can make you laugh, even when he's gleefully crossing the Moral Event Horizon. It also doesn't help that he's the Final Fantasy equivalent of The Joker.
 * Another example from that game might be the octopus Ultros. Ultros isn't really that threatening, truth be told, but he's a goldmine of hilarious one-liners.
 * Caulder of Days of Ruin fame is a fascinating example. Among other things, he for the lulz. And he makes it funny.
 * There's also Waylon, a greedy coward whose honesty about his selfishness gives him all of the game's best lines.
 * Many of the demons in the Disgaea series (except the psychopaths like fake/real Zenon, evil Adell, super evil Mao, etc) qualify for this trope.
 * Rayman: The Raving Rabbids. DAAAAAAAAAAAAAAAAAHHHHHHHH!
 * City of Heroes's Dr. Aeon. While he's one of the non-harmless examples of the trope, it's more because he's such a scatter-brained moron that he ends up posing as much of a danger to the world as to himself.
 * Foxbat from Champions Online. He's been described as an evil version of Adam West-era Batman.
 * Zorbak in Adventure Quest has transcended evil. He's Ebil! Mwahahah!
 * Escherion, the very first Lord of Chaos in Adventure Quest Worlds, becomes this trope at the end of the Chiral Valley saga when the hero reflects his inversion spell right back at him, inverting him and causing him to suffer the Humiliation Conga of ending up casting every spell he tries to cast on him/her on himself, and eventually turn himself into a harmless frog, which is a rather funny scene, to say the least.

""Definition: Love is making a shot to the knees of a target 120 kilometres away using an Aratech sniper rifle with a tri-light scope.""
 * The Lich Palawa Joko in Guild Wars: Nightfall once terrorised the entirety of the continent of Elona, whose forces were the greatest threat said continent faced until the Charr invasion many centuries later. Being unable to die or be killed, he had to be sealed away at the location of his defeat, and there he would have remained... if the plot hadn't required that you release him from his imprisonment for several very good reasons. But that's okay, all Joko wants is to reform his undead Army Of Darkness, which you've got to help him with as well. Astoundingly, he fails to be a threat for the remainder of the game, and while you're dealing with the Big Bad he's spending the rest of the time hilariously failing to get any sort of organisation from his mindless minions. What a guy.
 * Many of the player character's evil options in the Knights of the Old Republic games are hilarious. And then there's a certain over-eager assassin droid.

""QWAAAAAAARRRRR-" *KRZT* "I don't have the capacity for love, Janice. I was cursed by a tribe of gypsy ninjas when I was a kid!" "I know, Lance... I was in that tribe of gypsy ninjas!" *THWACK* "-RRRRK!""
 * GLaDoS from Portal.
 * in the sequel.
 * And Cave Johnson. Some of his quotes made his voice actor uncomfortable—to the point they had to cut a scene from Portal 2 because he refused to record Cave's lines for it, finding them too disturbing—despite this actor having played Complete Monsters in the past. And yet, he's hilarious.
 * The player in Evil Genius. Think Dr. Evil.
 * Ratchet and Clank Up Your Arsenal, Dr. Nefarious.

"Kaos: My head is awesome, I tell you! Fear it! Fear my GIANT FLOATING HEAD!"
 * King Dedede from the Kirby series.
 * Dr. Wily, from the Mega Man series. He pulls off evil plots like holding a Russian scientist's daughter hostage and spreading a robot virus, yet tends to use silly-looking robots, frequently wiggle his eyebrows, and beg for mercy upon his defeat. Every single time. The guy is a living paradox. The best example of this, is the time he stole the world's strongest robots, while wearing a rather flimsy disguise.
 * This is quite subject to a Funny Aneurysm Moment when you find out that
 * Hazama of Blaz Blue fame is a walking Crowning Moment of Funny. He's also the kind of guy who crosses the Moral Event Horizon nine times before he's even woken up. This perception has changed over time, however. As Hazama/Terumi becomes more and more saturated and pretty much everywhere and his motives comes off extremely shallow, Broken Base was formed, some just think he stops being laughable altogether.
 * Naturally Dr "Eggman" Robotnik of the Sonic the Hedgehog series, and only seems to be leaning further this way as of recently. Many alternate media representations are similar (see below). What do you expect from an egg shaped scientist who makes toy-like robots?
 * Grand Theft Auto San Andreas. James Woods as Toreno, the paranoid government agent. Disrepecting dead women to a monologue on how all modern conspiracy theories are no where near the truth.
 * General Sarrano is an evil, manipulative, foul-mouthed bastard who delights in the suffering of others, gleefully betrays everyone around him, and is generally an all-around un-fun guy to be around. At the same time, he's a hilariously over-the-top jackass with a never-ending stream of creative invective to toss at anyone and everyone around him.
 * Every villain in the Crash Bandicoot series.
 * Ditto for the entire Rogues Gallery of Earthworm Jim (even more so in the cartoon).
 * Most of the minor villains from the Pokémon Mystery Dungeon series games. However, they are often phased out when the not-so-hilarious Big Bad shows up.
 * King Bohan and Flying Fox from Heavenly Sword. King Bohan is voiced by Andy Serkis and is funny even when being a total bastard. Flying Fox has a very shrill voice and is even hammier than Bohan.
 * Kaos, the Big Bad of Skylanders: Spyro's Adventure. He's got the personality of Invader Zim, Large Ham and all. Though it should be noted he's actually far more compentant than his personality would imply. Doesn't make him any less fun to watch, however.


 * In the first Mother game, Hippies will try to attack Ninten with rulers. They'll also try to shout into a bullhorn that Ninten's mother was looking for him.
 * , from Skyrim. He's a jester who is a touch unstable, and also happens to be.
 * from Kid Icarus: Uprising. The few times when  gets dead serious, however,   actually pretty terrifying.
 * Sho Minamimoto from The World Ends With You, if only for how bizarre he is. Even when he's planning genocide and, he's somehow hilarious. A language or math certainly helps in that.

Web Comics
"Tarquin: But once he won the first two or three bouts I threw his way, I couldn't just slit his throat in the night, you know? He's a crowd favourite. It's weird, no matter how many no matter how many people he kills, the audience still think he's lovable."
 * Essentially all the villains in Sluggy Freelance except, arguably, Daedalus. Horribus, in particular, is a big example. One moment he's begging for his teddy bear (making him vice president to his empire, no less) and getting hit in the head with anvils in the middle of his Dramatic Entrance, the next he's incinerating minions.
 * Darksoul in the oft-underappreciated "Oceans Unmoving" storyline is a borderline example, whose humor mostly comes after you find out the plot twist;.
 * Even Daedalus can be funny. The only villains who weren't affably evil were Evil Aylee Clone and Kusari, who usually plays the straight man to the laughable evil around her, and even when dressed up as 'Hello Kitty' was more chilling than chuckle-worthy.
 * Even Kusari is learning sarcasm.
 * Lord Attez seems this way in Cwen's Quest. Although we only see very little of him, it seems pretty clear he is a hysterical & horrible person from his various traumatized children.
 * Black Mage in Eight Bit Theater could be downright hilarious while suffering.
 * Richard from Looking for Group.
 * Xykon from the The Order of the Stick. He may be a horrible threat, but he gets some of the best lines and comedic moments.
 * And now we have Tarquin, a man of remarkably dry wit and a love of heroic tropes who celebrated his reunion with his son with a festival of lights...made out of immolated prisoners.
 * Tarquin himself actually invokes this trope while talking about Thog

Web Original

 * in later episodes of Kate Modern, in a decidedly un-harmless way.
 * Doctor Steel.
 * There will be blood / It might be yours / So go kill someone / Signed Bad Horse
 * Diamanda Hagan runs on this.

Western Animation
"Negaduck: "When I throw... THE SWITCH!!!!!""
 * Don Karnage in Tale Spin. Let's see: Funny accent? Check. Eccentric and flamboyant? Check. Incompetent Minions? Check. Ruthless pirate who thinks nothing of dropping a child twenty thousand feet to his death or setting a town on fire with a Lightning Gun? Erm... check.
 * All the villains in Darkwing Duck, with the possible exception of Knight of Cerebus Taurus Bulba. Negaduck is a good example of a villain who pulls of both hilarious and dangerous at the same time.

"Darkwing (taken by surprise after already doing his dramatic intro): Er...I am the terror that flaps in the night. I am...the sur-surprise in your...cereal box... Bulba: Yes, yes, I know. I heard."
 * Even Bulba has his moments:

""This is Captain Jetstorm speaking. Please feel free to run about the tarmac and flee for you miserable little lives.""
 * The giant from Mickey and the Beanstalk. Great giant. Also, a cute little bunny rabbit.
 * Prime Evil, from Filmations Ghostbusters, was absolutely hilarious, thanks to a) the writing and b) Alan Oppenheimer's Large Ham acting.
 * Like everything else in Freakazoid, the villains were hilarious.
 * Lex Luthor in the Superman movies is funny for many reasons, but it meshes well with the character. Lex Luthor in Superman: Brainiac Attacks is ridiculously campy, and it doesn't... work... well...
 * Bizarro is a creature with all the powers of the Man of Steel, and an intellect that insults egg plants by association. To be fair, he may actually be quite competent, especially in the DCAU where he is the only one to notice that something is wrong with Lex Luthor (namely that Lex and Flash are body swapped), but because he expresses himself in opposite action every time he speaks, no one gives him the time of day.
 * Most of the villains in Kim Possible are laughable, especially Dr. Drakken (with Shego's running commentary serving to highlight his laughability). Even the Scary Dogmatic Aliens, who can't grasp English idioms and have a goddam Off-button in their ship (except when they threaten to kill Kim and mount her in front of Ron).
 * In Transformers Animated, Blitzwing by himself is funny, particularly when his "random" personality is in control ("Ooh, I wanna see him turn into a fire truck, can I, can I, can I?"), but him and Lugnut sniping at each other is hilarious.
 * Other villains have their moments, too, some more than others. Swindle, for example, is an Arms Dealer who acts like nothing so much as an overly-excited infomercial host. (In fact, his mannerisms were based partly on Ron Popeil.) And, because this show is so Merchandise-Driven, you can have your own little plastic Swindle for just $10.99! But Wait! There's More!
 * Dave the Barbarian's Dark Lord Chuckles, The Silly Piggy. It's in the name. For bonus points, this is how he actually announces himself.
 * Bebop and Rocksteady from the 1980s Teenage Mutant Ninja Turtles cartoon. Sometimes Shredder and Krang get in on it, too.
 * Essentially all the villains from The Venture Brothers, but the Monarch stands out.
 * The Joker from The Batman. From his bizarrely eclectic outfit to his equally bizarre way of fighting, the man simply cannot pass on the opportunity to do anything with a comedic twist. Naturally, some fans were not pleased.
 * Others found him the funniest Joker yet and quite terrifying.
 * The Joker from the DCAU universe definitively qualifies as well. In fact, he even supplies the Trope Picture (more specifically, it was taken in his first scene in Batman Beyond: Return of the Joker where he briefly fakes out Bonk with execution, shortly before doing so for real).
 * Aku from Samurai Jack is so much fun to watch that you often forget he's Made of Evil, as he takes a break from hunting Jack to villainously order a pizza, subjects frightened children to his terrible storytelling, and swears revenge in a helium voice while in the form of a kangaroo rat.
 * The "storytelling" thing may have been an attempt to raise the next generation to revere him. It fails, obviously.
 * All of the villains on The Powerpuff Girls. Mostly Him and to a slight lesser extent Mojo.
 * The titular protagonist of Invader Zim. Or just the Irkens in general, really. Who knew planet-scale genocide could be such a riot?
 * Dr. Robotnik/Eggman of the Sonic the Hedgehog games is humorous but legitimately threatening most of the time. However, in Adventures of Sonic the Hedgehog, he is depicted as bumbling and hilarious, aided by the stellar Large Hamming of the late Long John Baldry.
 * Almost all renditions of the doctor are this in heavy doses (save maybe the Sonic Sat AM version, though even he isn't void of comical moments).
 * Heloise from Jimmy Two Shoes is an Ax Crazy Enfant Terrible known for her Yandere attraction to Jimmy. As you might guess, she's quite hilarious. Lucius can be this as well.
 * The Red Guy from Cow and Chicken.
 * Jetstorm from Beast Machines is Ax Crazy even by Transformers but his Large Ham personality and horrible sense of humour make him one of the most enjoyable villains in the entire franchise.


 * Skybite of Transformers Robots in Disguise is the Ineffectual Sympathetic Villain version.
 * Any Predacon who isn't Megatron/Galvatron.
 * Phineas and Ferb has Dr. Heinz Doofenshmirtz. Yes, he wants to take over the entire Tri-State area, and has created everything from Killer Robots and mind-control helmets... but he's so bad at it, it's hilarious!
 * Of course, Compared to his alternate universe self, Doof-2 from Phineas and Ferb The Movie: Across the 2nd Dimension, he's a pretty decent guy. Doof-2 was willing to kill complete innocents and his alternate-self, just for the sake of it. Though he still fills this trope by, among other things, announcing their doom with a sock-puppet.
 * Every villain from The Little Flying Bears, most notably Skulk and Sammy.
 * Discord from My Little Pony Friendship Is Magic is much like The Joker in terms of this trope. One moment you'll be laughing at him, the next you'll be completely horrified as he breaks and brainwashes the Mane Cast.
 * Mostly because Discord (or as the fans call him DisQord) is basically Q from Star Trek: The Next Generation after he got bored with annoying bald federation captains.
 * A few villains in The Spectacular Spider Man fit into this, namely the Green Goblin, who effortlessly makes jokes and quips back at Spidey while at the same time being a relatively Ax Crazy Magnificent Bastard. Rhino also counts too, as he is a typical Dumb Muscle with several funny lines and scenes, but gleefully attempts to "impale Spider-Man's heart on his horn".
 * Skeletor from He Man and The Masters of The Universe became this in the Filmation cartoon—in the original minicomics he was a fairly serious villain, but since censors were constantly breathing down Filmation's neck about what they perceived to be a horribly violent cartoon about a sword-swinging barbarian, they decided to make the scary man with a Skull for a Head less scary by playing him for laughs. Though still an evil schemer, the cartoon Skeletor was turned into a Laughing Mad Deadpan Snarker who kept cracking one-liners in which he insulted the world in general and lamented how he was Surrounded by Idiots. The 2002 remake of the show turned him a little more menacing and threatening, but kept his sarcasms and general tendency to get all the best lines in the show.