The Canadian Sleeman Breweries recently launched a new ad campaign playing up the bootlegging activities of the company's founder John Sleeman. It also plays up George Sleeman, whose business was threatened by prohibitionists who'd managed to get anti-liquor laws passed in his hometown, after which he ran for mayor himself and repealed the prohibition laws.
As do most of the other villains, especially Mello and Ryuk.
The author himself was shocked that so many people seemed to love evil characters such as Light. He probably decided to have Light lose and die at the end simply because so many people wanted a character he purposely made more evil to win.
That outcome was almost certainly 'planned from the start'. However, they probably made Light's epic crash and burn ending even harsher than originally conceived to drive home what they really thought of their "hero".
Britannia as a whole. A ton of fans tend not to see all the nazism and casual mass murder because of all the pretty uniforms and badass mecha!
In the Bad Future of Mahou Sensei Negima!, Negi's students capture Takane D. Goodman and her posse, and (painlessly) Mind Probe them to know where Negi is imprisoned. This leads to the following exchange:
Sir Crocodile of One Piece pulls this off almost too well. A list of atrocities can fill a book. However, he commits his evil acts while dressed like a blinged-out mafia don, complete with a ring on almost every finger and a pimpin' green fur coat. Not only that, but he controls an organization made up of Crazy AwesomeBadasses, owns a casino, trots around with a scantily-clad hot chick as his #2, keeps incredibly dangerous predators as pets, and is also made of and can control sand, and he has a hook for a hand. That's just darn cool. But he's such a bastard...
You can't one up a bastard-8 foot plus tall-knight-marine-Godfather-insanely choking-likely rapist-pirate who kills people by touching them named Crocodile...unless you are a silent-8 foot plus tall-gangster-pirate-superstrong-hetero-ninja who is also a sword named DAZ BONES. He's like Raven from Tekken, only bigger, stronger, a pirate, has no need for weapons, and has the greatest name ever hands down. His loss, or, actually, both of their losses, lost the strawhats fans.
All of the villains are incredibly awesome in their own singular ways. Though the best way to put it is...
Y Ruler Of Time: on One Piece's villains How is it possible that these guys are so awesome I want to root against the Straw Hats?!
Negishi from Detroit Metal City is hated for his music, and generally considered to be a spineless douche by virtually anyone...until he becomes Krauser II in Detroit Metal City, a Death Metal band. And once there, he embodies this trope.
Also inverted with the Xcution / Full-Bringers, who are insufferable sneaks who are much weaker than the previous enemies and have overall less interesting powers.
Played straight with the Vandenreich Quincies who have pretty much dominated all of Soul Society with their powers, while looking awesome in their Quincy outfits. Especially their leader who has managed to kill Yamamoto that makes the latter look like an amateur.
Cobra, Midnight, Jellal, and Erza Knightwalker from Fairy Tail
Lyrical Nanoha both uses and averts this. Fate, the Wolkenritter, and most of the Numbers were cool, but Precia and Quattro were...bitches, and Jail is something of a Base Breaker.
Lordgenome from Tengen Toppa Gurren Lagann. On the one hand, he is a ruthless tyrant and Anti-Villain who doesn't care if his daughters live or die...on the other hand, he has rugged good looks and a cool-looking and powerful Humongous Mecha, and he can fight Mini Mecha with zero weaponry whatsoever; by which we mean his bare hands, and almost tank a Big Bang-level attack with a scaled-up version of his mech.
The Laughing Man from Ghost in the Shell: Stand Alone Complex. He has tons of copycat supporters, and in one episode, Motoko visits a chat room devoted to discussing how cool and rebellious the participants think he is.
Femto a.k.a. Griffith in demon mode from Berserk. He is, considered by most of the fanbase, the most despised villain for what he has done over the course of the story (and particularly for doing one very heinous deed to a lovable character). Surely, his actions are unforgivable!... But DAMMIT! Why does he have to look so friggin' awesome in that quasi- evil costume (since he's technically naked)?! And dude - he has the power to bend reality at his will!How awesome can you get??
Kotomine Kirei from Fate/ZeroBadass Normal priest, with bullet-proof vestments, extreme skill in Baji quan and insanely accurate and deadly knife skills. Also Gilgamesh, King of Heroes, with the largest sense of entitlement/ego this troper has ever seen in a villain to date. And they team up.
Berg Katse from Gatchaman has hir fans. The messed-up childhood and cool new toy nearly every episode probably have something to do with it, even with the silly ears.
The Joker, in most incarnations. It doesn't matter whether he's a giggling, goofy clown prince of crime (e.g. the 60's Batman television series), a mass-murdering sociopathic Monster Clown (e.g. The Dark Knight), or a seemingly impossible mixture of the two (e.g. Batman The Animated Series), he will inevitably overshadow every other character, have all the best lines, and, while Batman will always have the best toys (he's the goddamn Batman, after all), the Joker will find the most creative and spectacular ways to use the tools at his disposal. No matter what he does or who he does it to, he will make you laugh, because of the simple fact that he's just that good.
Discussed in an issue of Batman: Black and White, a short-story anthology. In this story, Batman and the Joker are actors playing their comic book roles as if they were roles in a movie. The Joker brings up the fact that Batman always gets to make a big, dramatic, splash-panel entrances, complaining that he never gets to look that good. Batman then points out that the Joker always gets the best lines, while he just has generic crime-fighting hero lines.
Batman in general is a magnet for this. When your main character is a traumatized billionaire dressed as a bat and you have villains drawing your attention far away from that, it really says something.
Le Tueur: I have a confession to make: I only like the Batman because he has the best villains!
In the Marvel Universe, Doctor Doom practically owns this trope. He's a science genius who wears a cloak and a suit of armour, rules his own country, and lives in a castle. And refers to himself in the third person! DOOM insists on it!
Monsieur Choc, the main villain in the Tif Et Tondu Belgian comic book series. He is considered so cool that he is the reason the series became popular in the first place, and the recent re-releases deliberately put him as the focus on the covers of the stories chosen.
The titular character of Lucifer is a horrible, destructive person, but (likely in reference to Paradise Lost below) is incredibly awesome all the same.
Played with in Sin City. The pure evil characters are usually pretty ugly and often cowardly, or just plain creepy. Some of the good guys, however, are at the extreme end of anti-herodom. The most popular tend to be Marv, Dwight, and Miho, who would normally be considered bad guys in any other work. They are also damn cool.
One arc in The Sandman features a convention of Serial Killers who think of themselves as this (they pick impressive-sounding names for themselves and think of themselves as Übermensch), but as the reader sees more of them their combination of petty delusions of grandeur, personal insecurities, copying of their predecessors and occasional stark-raving-madness becomes more obvious. This is ultimately confirmed when the eponymous Morpheus gives them all a blistering "The Reason You Suck" Speech, tells them that "Until now, you have all sustained fantasies in which you are the maltreated heroes of your own stories. Comforting daydreams in which, ultimately, you are shown to be in the right" and then uses his power as lord of dreams (and thus fantasies as well,) to strip them of their self-deception so that "you shall know, at all times, and forever, exactly what you are. And you shall know just how LITTLE that means."
In The Official Fanfiction University Of Middle-Earth, this gets deconstructed with the subject "Evil Is as Evil Does 101", taught by Sauron himself, to teach that Evil is more than calling yourself evil because it's cool and dark and edgy. Like causing a river of blood, at least.
Almost every Disney villain imaginable turns out to be cooler and much more lovable and funny than the protagonist. Having really awesome Villain Songs probably helps.
Hades from Hercules. Roger Ebert even said Hades brought, "something of the same verbal inventiveness that Robin Williams brought to Aladdin." In addition, he's such a fast talker he got The Fates, Megara, and Hercules himself to obey his whims, all while being a Card-Carrying Villain in the whole process.
Honest John and his sidekick, Gideon, from Pinocchio have one of the coolest songs in Disney history: Hi Diddle Dee Dee
Yzma from The Emperor's New Groove is arguably the most entertaining character (with the possible exception of Kronk) in the movie in her own right, completely setting aside the issue of the protagonist being less than likable. And if her initial Villain Song, "Snuff Out The Light" had ended up in the film, she would've been bumped up even further.
The villain of The Princess and the Frogbreathes this trope. Dr. Facilier (voiced by Keith David) is a nasty piece of work: powerful, scheming, persuasive, stylish, charismatic, and he has an awesome Villain Song. Now this is following tradition!
Judge Claude Frollo from The Hunchback of Notre Dame fits, too, and he has not one, but TWO heroes to overshadow. It helps that he has probably the most audacious and amazing villain song ever, and that neither hero is really interesting enough to stand up to a character with as many layers as Frollo. And then there's Tony Jay's voice.
Clu's aforementioned Dragon, Rinzler. He has a cool outfit and mad fighting skills, and his being Tron himself not only makes him cooler, but also makes his Heel Face Turn and subsequent Heroic Sacrifice that much more poignant.
Really, any villain played or voiced by Tim Curry will shine so much that it can be almost dangerous in how awesome they turn out. Screw the protagonists, let's throw them in a death trap so we can hear the bad guy do that evil laugh again!
Legend thrives on this. People may complain that Tom Cruise isn't wearing pants and there's glitter on everything, but those horrifically cheesy lines the Lord of Darkness provides? Priceless.
Subverted in Spider-Man 3: when he's possessed by the symbiote and 'evil', Peter Parker thinks he's this, but is still noticeably geeky and clueless — he's just now arrogant and obnoxious as well (but he does become the most supernaturally smooth tango dancer since Gomez Addams). Furthermore, the symbiote eventually merges with Eddie Brock, who is noticeably slimy, unctuous, and creepy.
Played perfectly straight by Spider-Man 2, though. Doctor Octopus is made of win.
In terms of Spider-Man movie characters, Venom would have been the epitome of this trope if he hadn't been killed off so quickly.
Norman Osborn was kind of cooler as a business scientist than as the Green Goblin, though, apart from a few aerial acrobatic moments and maybe his first murder...and he was coolest while talking to himself and wigging out.
Darryl Revok of Scanners. Bad, bad dude. Pow. Michael Ironside always invokes this trope, even when playing a nominally good guy.
Applies to various evil monsters in the Godzilla movies, especially the Godzilla Final Wars version of Gigan that gets chainsaw hands for the final battle. Also applies to Godzilla himself in the films where he is evil.
The Lion The Witch And The Wardrobe, Queen Jadis in her bright attire out-cools almost all of her opponents on the battlefield, possible because actress Tilda Swinton is inherently cool in all her roles. In Prince Caspian, nasty uncle Miraz has some of the best lines (although it's hard to beat Edmund), thebest beard (not counting Aslan's), and probably the genuinely best set of armour.
Miraz was less cool in the book, but the all-dialogue scene in the Howe with the hag and the werewolf was one of its most memorable bits, mostly due to the werewolf's creepy bragging. It ranks up there with Aslan growing delicious grapes for everyone and the duel.
Blood Feast is a great example of this. Fuad Ramses is the only good character in the whole movie.
The independent horror/comedy film Behind the Mask: The Rise of Leslie Vernon has the coolest new killer who looks up to Jason and Freddy, who lets a crew document his future reign of terror. Leslie Vernon is not only charming, witty, and genuinely friendly; before beginning his legacy, while in a library, he says, "Paradise Lost? Found it!" while grabbing John Milton's Paradise Lost. And he keeps turtles as pets and then tells the young woman interviewing him that he only kept pets that he could eat. His mask is amazing as well.
Avatar. Colonel. Miles. Motherfucking. Quaritch. Works out to stay strong on a planet with weaker gravity, commands a platoon of tough ex-armed forces mercenaries, rocks a customized mecha with a freakin' dragon painted on the gun barrel and a huge-ass combat knife, holds his breath, kicks down a door and steps into toxic air simply to pursue a traitor with his assault rifle, sports scary scars on one side of his face, and rides to battle in the Dragon Gunship while sipping fine Arabica Roast coffee. That he possesses the courage and determination to keep fighting no matter the odds merely adds to his Colonel Badass bona fides.
While the men of Gondor are just a bunch of unshaven men wearing plate mail, Sauron has not just his orcs and trolls, but the soldiers of Rhűn, spearmen with remotely creative looking armor and warchants that sound like the Haka, and the Haradim, who ride Műmakil, which are essentially the ninety foot tall war elephants that Hannibal had wet dreams about. Their impact onto the frontlines of a charge from the Riders of Rohan (which had routed an orc army of dramatically superior size) was a moment where even the orchestra abandoned the forces of order as the Haradim rampaged through the helpless Riders until driven off by the Strong as They Need to Be protagonists.
Plus, Sauron's armour is ridiculously cool looking. Spikes everywhere, a huge, crownlike helmet that looks like a horse's skull, and the whole thing has a faint and delicate poison ivy motif etched into it.
Also, just as applicable, Saruman. It helps being played and voiced by Christopher Lee.
For a giant eyeball, Sauron is quite cool-looking himself. And then there's the Nazgűl.
Even though he was a minor bad guy, the Uruk-hai captain that popped up at the end of the first flick was also cool. He's one of the few characters that gets to smack Aragorn around a little, does a really cool Captain America-like shield throw, and has the audacity to shove Aragorn's sword into his gut the rest of the way with utter contempt and defiance.
The Balrog, who is probably the Boba Fett of the movies series: he's a One-Scene Wonder that takes out a major hero for the remainder of a movie and is one of the more memorable characters.
Keyser Soze of The Usual Suspects is clearly a monstrously evil man if even half of the things said about him are true, but his coolness in doing them is indisputable, particularly given the famous twist ending has made him a by-word for the Diabolical Mastermind.
Scarecrow from Batman Begins, who has an awesome answer to every problem that comes his way. Mob boss knows too much about his secret identity? Scarecrow pumps him with so much fear-gas that it drives him insane. The Batman shows up in his hideout? Scarecrow lights him on fire and kicks him out the window!
Rounding out the trilogy, The Dark Knight Rises introduces Bane. His appearance would suggets your typical dumb brute, but he's actually a Genius BruiserManipulative Bastard with a sympathetic backstory. He opens the movie by cutting a plane in half mid-flight and only proceeds to get more awesome from there. The first time he fights Batman is almost hilariously one-sided, he has a Cool Mask that makes his voice omniously low, and he completely takes over Gotham with minimal effort. He breaks Batman's spine (sort of) and sends him to a nigh-unescapable prison for several months.
Subverted with Roman and Minnie Castevet in Rosemary's Baby - the tackiest Satanists ever.
Gabriel from Constantine. Also, the Devil and Balthazar.
The Decepticons of the Transformers, as they usually are in most Transformers series. Case in point: the Autobots are limited by their desire to make Earth their second home, and must take on friendly appearances and altmodes to blend in with civilians. The Decepticons, on the other hand, have no such limitation. Therefore, they take on the forms of tanks, F-22s, and satellites, or, in the case of Megatron and Shockwave, simply reject reformatting their original forms. Additionally, they have access to numerous weapons, ranging from Transformer-sized fighter jets to a giant mechanical worm that serves as a war beast. Even the humans are aware of this, as Epps, at one point, asks to no one in particular "How come the Decepticons get all the good shit!?"
Megatron (as mentioned above) is possibly the best example of this among the 'Cons themselves, especially in the first movie where he's at his most Ax Crazy and Badass, and is easily the most interesting and entertaining of the robots in the movie, despite getting less screen time than the humans or Autobots. Oh, and he's voiced by Hugo Weaving (see above).
While Cats And Dogs gets flak from cat lovers for making all felines villainous, it does redeem itself a bit with this trope, with Mr Tinkles and his henchmen often claiming more amusing personalities and gags than the heroic dogs.
Sharptooth from The Land Before Time. Despite killing Littlefoot's mother, there is no doubt he is this, and probably the coolest Tyranosaurus ever to appear in an animated film.
This has notoriously been the biggest problem with John Milton's Paradise Lost. Satan is, in fact, so much more interesting to read about than God or Christ (except when the latter gets into His chariot) that William Blake thought Milton was "of the Devil's party without knowing it." The immense Misaimed Fandom hasn't helped. Even though what looked like was going to be an awesome battle scene over Earth turned into Satan running away after realizing that he's not cool anymore, which the sneering angels already knew, and the rest of the story after that shows him being humiliated worse until he wins with Eve and the narrative loses interest in him, for the most part. He's still falling the whole time. But who gets past the first couple of books, anyway?
Claudius the God is the story of Emperor Claudius, portrayed as a decent and honorable man thrust unwillingly into a position of ultimate power. I, Claudius chronicles the reigns of Augustus (and his wife Livia), Tiberius, and Caligula. Guess which one is the most fun read? In case you need a hint: one chapter of Claudius the God is devoted to the protagonist's visit to the doctor.
Averted in the Tortall Universe. Kel is disappointed that Blayce is not some grand wizard, and instead, just a short and ugly wimp. His muscle isn't too impressive either.
Subverted in The Screwtape Letters. Devils are bureaucratic, cranky, selfish killjoys who actively try and reduce the pleasure sinning gives people.
All of the Four Horsepersons of the Apocalypse fall under this trope, as the parts featuring one or all of them are easily the coolest and most awesome parts of the book.
Although you wouldn't know it from reading the actual book, where he is hideous, disgusting, and creepy, Dracula is essentially responsible for the entire western world's vampire obsession.
Lord Voldemort He's one of the most powerful and cunning characters in the series and has a kickass army of Dark wizards and various sinister creatures at his disposal.
Dante's The Divine Comedy is split up into three poems, detailing the narrator's journey through Hell, Purgatory, and Heaven. Guess which one is the best known. Similarly, while everyone knows about the Seven Deadly Sins, not too many people are familiar with the Seven Cardinal Virtues (Humility, Generosity, Chastity, Meekness, Temperance, Brotherly Love, and Diligence).
In Family Matters, Extraverted Nerd Steve Urkel's formula based off the "cool gene" transformed him into Stefan Urkél, who was suave but amoral. However, this was subverted in Stefan's next appearance, where Steve revealed that he'd accidentally involved the "evil gene" in the formula; from then on, Stefan was both cool and nice.
For some reason, evil, batshit insane, brain-stealing villain Sylar from Heroes is a lot cooler than sane, geeky Sylar. Apparently, evil wears contacts. Ditching the specs (and also acquiring stubble) seems to be mandatory for characters taking a walk on the dark side. Consider Wesley from Angel: glasses on — the scholar and gentleman of the group. His attempts to be baddass are laughable. Glasses off — beds Lilah, keeps a woman tied up in his closet, breaks rogue Slayers out of jail, and tortures junkies for information.
Spike, who, before he was turned into a vampire, was laughed at and wrote "poncy poetry", whereas when he was sired, he became all bad ass. (His actor, James Marsters, has since made this his specialty, as the rest of this page shows.)
Evil Angel is about seven times cooler than Good Angel. It probably has to do with the lack of brooding. Evil Angel is funny. He also gets several times smarter when he goes evil, which was lampshaded in the episode Awakening.
In an alternate universe, Xander and Willow got rid of their geeky sides after vampirization, instead opting for black leather and a smooth demeanour.
Brother Lassar. He's played by Anthony Head. Nothing more needs to be said.
Captain John Hart of Torchwood. Kills someone and then says, totally bored, "Thirsty now". Casually admits he killed someone, apologises for the mess, clears a bar of all he considers ugly, and orders one shot of every drink in the bar. Then drinks what appears to be a bottle of Vodka. In one go. With no noticeable side effects. Comes out with regular quips. The only person who really gets the better of him is Gwen Cooper. It helps the same actor played Spike in Buffy, and there is a definite similarity between the two.
The villains in Batman were always more colorful than Batman and Robin. No wonder so many established actors were willing to play them!
Mark Shepherd plays delightfully evil characters in Firefly, Supernatural, and Leverage that seem to come out on top and have lots of fun while doing so. From his shiny shoes to his amazingly charismatic voice, he effortlessly manages to outshine and out-cool the regulars on the show.
Supernatural: Castiel seems to get more bad ass and confident as he turns to the dark side in Season 6.
Also, lots and lots of the smarter villains. Including a season-seven appearance by an aging James Marsters, playing an apparently immortal witch capable of treating our god-killing heroes like gnats. Many of the coolest ones get Enemy Mine situations (like Crowley) or turn out to be fairly decent, or at least relatable, like Patrick the Gambler.
Scorpius from Farscape is this, right down to the leather clothes.
Generally averted in Criminal Minds, where the various killers usually come across as rather pathetic as soon as they're not in a position of power, (they are usually trying to fulfil some fantasy or make themselves feel better about some perceived deficiency in themselves,) and the whole focus of the show is on The Profiler team proving themselves intellectually superior to the killers by outsmarting and catching them. The only exceptions to this tend to be killers like the Boston Reaper, who gives off this vibe due to his extremely high level of competence and his apparent lack of any fantasy-fulfilment (he just kills because he's an evil sadist who enjoys tormenting his victims and being notorious).
Often subverted in the lyrical content, however. A lot of black metal is individualistic in the Nietzsche Wannabe tradition, while death metal tends towards either nihilism or more traditional "punk ethics". In these cases, the Evil Is Cool aesthetics are intended to be provocative and anti-social, rather than to be taken at face value. It's much less a rejoicing in actual evil as it is simply an embracing of this trope at an aesthetic level. Lyricists are aware that people, and they themselves, find villains, darkness, and horror to be interesting. As bands like Cannibal Corpse have said, very few extreme metal bands take their own lyrics seriously, and those who do are usually rather unstable. As Black Sabbath also stated, they're intended to be viewed much in the same light as horror films. A lot of bands simply use their music as a Villain-Based Franchise.
Dr. Steel. Many fans like him not for the music, but for the incredibly cool Steampunk Villain getup.
It was this concept that led WCW to temporarily take the crown as the #1 wrestling promotion in the world with the New World Order. Although the nWo was comprised of heels, the charisma of its top members like Hogan and the Outsiders, combined with some innovative marketing (this announcement has been paid for by the New World Order), attracted many fans to their side.
Many professional wrestlers profess to enjoying playing a heel far more than playing a face. For some of them, this can bleed through into their performances, such that a wrestler who undergoes a Heel Face Turn actually loses popularity due to his lackluster performances afterwards. There's a reason a lot of professional wrestlers and wrestling fans tend to think Good Is Boring. Faces tend to fall into being good role-models or, because Good Is Dumb, lose any Genre Savvy skills they had as a heel and end up with no real personality. Heel Face Turns often result in promos that don't consist of anything more than saying, "I respect my opponents," "I want to prove that I'm the best," etc., as opposed to being able to take advantage of their creative mic skills. This is probably why many of the most popular wrestlers of the last twenty years have been tweeners or even heels, as opposed to faces.
A good heel turn can also save someone's career and end up making them a star after a disastrous or boring face run. See The Rock, Randy Orton, John Cena, and Santino Marella for prime examples of this in the past decade.
An interesting phenomena is when, through excellence in performance, an interesting persona, and good mic skills, a supposed Heel wins over the crowd and becomes a fan-favorite Heel.
When Kurt Angle first joined the WWE, he was considered to be a yet another "real" fighter who had not yet paid his dues as a Jobber. However, his ring skills were incredibly impressive, and his two gold medals (1996, Atlanta Olympics, and 1995, World Championships) weren't fake. Even more impressively, he won one of them while having a broken neck. And then, something miraculous happened. During a Monday Night Raw episode, the crowd started chanting "You Suck, You Suck" along with Angle's wrestling music. His reaction not only clarified his persona, but it also created the most loved heel in the history of wrestling.
CM Punk doesn't like you but everyone likes him due to his rebellious and frank attitude about WWE. He often gets cheered even when he expressly disparages against the audience because no one disagrees with his claim that he's the "Best in the World".
From the spinoff Dawn of War computer games: Eliphas the Inheritor is universally considered one of the top five characters, as is Gorgutz 'Ead 'Unter. Mainly because Eliphas is almost painfully badass and Gorgutz is awesomely insane.
Magic: The Gathering reintroduced the Phyrexians, who want to corrupt and assimilate the entire multiverse. Naturally, half the fan base takes their side. 51%, at last count, in fact.
They eventually won the popularity contest and took over the world which they were fighting for.
Exalted: Infernals are widely considered to be way more awesome than Solars. The Solar charmset is generally viewed as kind of bland (the overriding theme is "I am really good at this" with a few paragraphs for each Charm describing what they are good at and how that is expressed), while Infernals do things like turning a glass of water into a tentacle or undergoing mitosis. Solars have an ascension path of "Solars with higher Essence", while Infernals can forge themselves into new Primordials. Abyssals, on the other hand, are much less popular due to flaws in their Charmset and limited support for character paths other than "angsty penitent" or "kill the world and piss on the ashes".
The Shakespearean characters every actor wants to play are his most notorious villains, Iago of Othello, and the eponymous Magnificent Bastard of Richard III. Similarly, every actress wants to be Lady Macbeth, his greatest villainess. The roguish buffoon Falstaff was so popular that Shakespeare gave him his own spin-off comedy in which he is the protagonist. (By royal command, no less - Queen Elizabeth turned out to be one of Falstaff's admirers.)
Similarly, the really cool characters in opera are not the tenor good guys, but the jealous/mad/pervert baritones and the creepy basses who sing low notes of Doom. Who would ever prefer the nice, boring tenor Don Ottavio to the Magnificent Bastard Don Giovanni? Or, in Der Freischuetz, prefer the utterly bland Max to the ribaldly malevolent Kaspar?
Despite the fact that The Phantom of the Opera is an obsessive, controlling, homicidal, textbook 'bad boyfriend', he is inevitably the one the audience roots for. You'll have to scour through hundreds of Phantom/Christine ShippingFan Fics to find one Raoul/Christine, and it's better than even money that actors would rather play the Phantom. Why? Raoul is a largely ineffective ponce; Erik drops chandeliers on people. Plus, in the case of the musical, he gets all of the cool songs and a stylish black cape.
Christopher Marlowe was good at writing this type of character; the best-known example is Mephistopheles in Doctor Faustus, but Tamburlaine of the play of the same name and Barnabas of The Jew of Malta also qualify. Oh, and the evil ghost Machiavelli.
Mr Doolittle of My Fair Lady is an amoral drunkard, but for all his faults, "With a little bit of luck" is so charming, we can't help but think this guy cool.
The entire point of the Villains Tonight! stage show on the Disney Cruise Line, featuring Hades, Maleficent, Ursula, Jafar, Yzma, Captain Hook, Cruella DeVil, and Dr. Facilier all together in one show!
Used quite a bit the Devil May Cry series. Dante's enemies (primarily his Evil Counterpart, his brother Vergil) are pretty darn cool, but Dante still generally mops the floor with them with style.
Saints Row: every chapter ends in an Eviler than ThouCoup de Grâce. Almost everyone kisses the Protagonist's ass by complimenting his/her murderous psychosis. Arguably the coolest character in the series so far is unrepentant mass murderer Johnny Gat.
Also the point of Dungeon Keeper, where you are the Dark Lord who builds his eldritch underground kingdom and throws adventuring heroes in torture chambers. Remember: Evil is Good.
It is primarily for this reason that Knights of the Old Republic and similar games have an evil option. KOTOR is further helped in this regard, since Star Wars villains are generally among the most Badass characters in all of fiction.
This is acknowledged in the second game, where the opening screen shows one of the various Sith Lords of the game. Go bad enough, and your character will replace them after you complete the game.
The King of KOTOR Kool himself - the psychotic, homicidal HK-47 assassin droid. "Definition: 'Love' is making a shot to the knees of a target 120 kilometers away using an Aratech sniper rifle with a tri-light scope." He is far and away the single most beloved character by the meatbags playing the games.
Both KOTOR games actually provide especially good foundations for this. In the first game, you're playing an amnesic Sith Lord, and if you decide to reclaim your former glory, characters will acknowledge you as such. And KOTOR II just takes it Up to Eleven. This time, you aren't technically on a mission to be the hero, so it's not even expected of you. In this game, you get to wear a black Badass Longcoat, teach your companions the way of the Dark Side, cut your way through small armies like a knife through butter, take out entire ambush teams of mercenaries with a single Force Storm, curbstompJedi Masters in a duel, steal their techniques, then suck up their power for yourself...and that's all before you get Force Crush, against which there is no defense! The Light Side path may have more plot exposition, but the Dark Side one is definitely the cooler one.
Also from Star Wars, Star Wars Battlefront II has you playing as the 501st Legion in the "Rise of the Empire" story mode. Needless to say, after the Evil Empire rises and the 501st becomes evil, they're still awesome.
Another Star Wars example: TIE Fighter. Darth Vader is your wingman. That is all.
The Command & Conquer series always has fiendishly enjoyable Evil campaigns. Especially in Red Alert, the evil is served with a generous side of Large Ham. Starting in Tiberian Sun, Nod had much cooler outfits than GDI, and in Tiberium Wars, they had cooler looking vehicles. This is somewhat offset by the fact that Nod has a tendency to favor looks over practicality. GDI's ground vehicles tend to be better, and their soldiers actually look like soldiers, while Nod's look like a bunch of, abeit cool looking, KKK rejects.
Pick a Final Fantasy game, go ahead, pick one. To recount some of the more famous examples:
Kotomine in Fate/stay night...well, he's cool enough that the fact he has a mullet ceases to matter. Possibly helped along by every scene contrasting him to Shirou. The other Big Bad, Zouken, is not cool. Or likable. Or, well, tolerable. You just kind of want him to hurry up and die already. Helped by the fact that Kotomine really knows how to talk; it's hard to be bored of his often long speeches. Most of his speeches have very little to do with him being evil or evil in general.
Looking back at Guilty Gear, many people were turned off by Ky Kiske because he's too much of a goody two shoes. Then, in BlazBlue, he's given an Expy in form of Jin Kisaragi, a twisted, erratic Jerk Ass whose unwholesome personality was nonetheless well-met by many fans.
There is the matter of Hazama, a.k.a. Yuuki Terumi, who's taken the role of the Big Bad of the series. He's an arrogant Troll who's even more abrasive and mean-spirited than Jin and has more or less fucked up the lives of everyone in the series, most of all, Noel, when he transforms her into Mu-12. Fans love him because he's funny, handsome, and a cool dresser.
Although over time, people somehow got sick of Terumi being constantly pushed to attention and looking too invincible nearing Boring Invincible Villain status. On the other hand, this title now goes into his partner Relius Clover, who's not as pushed to attention, but remains a Large Ham, composed, a cool dresser, rugged, and just as depraved as Hazama (or even more)
Shadow the Hedgehog from the Sonic the Hedgehog series, at least, when he was initially a villain. Nowadays, he is more of a Base Breaker. Dr. Eggman is probably just as beloved a villain as Sonic is a hero.
Tyranitar and Hydreigon, a Godzilla/Tyrannosaurus rex and a King Ghidorah/Hydra Pokémon respectively. Both of them are extremely savage and destructive, are Dark-types who use actualdarkness powers as compared to most other Dark types, and their BST of 600 makes them comparable to some legendaries in terms of power. (Unsurprisingly, they're both in the OU tier.)
Houndoom is a Dark-type literal Hell Hound and one of the more popular Pokémon.
One of the best-known and most powerful "evil" Pokémon, Mewtwo.
By far the most popular "shiny" Pokémon coloration belongs to Charizard, already an enormous Ensemble Dark Horse. In its shiny form, it gets an evil-looking black color scheme with blood-red wings and sinister red eyes (this form was actually depicted as a Darkness-type in the TCG in one card, and the card is one of the most sought-after and ridiculously overpriced cards today).
A lot of the evil organizations such as Team Rocket can be this with their stylish uniforms, cool hideouts, and intimidating Pokémon teams.
Unlike Reshiram and Zekrom, Kyurem is shaping up to be a truly evil (or at least corrupt) Pokémon by nature that eats humans. And it's a giant icedragon that can absorb Reshiram or Zekrom to switch forms and become more powerful.
Kratos from God Of War is an excellent example, as his very anti-heroic tendencies make him a more interesting character. He's a complete Badass. Also, Ares, to a certain extent, though he is not so cool as Kratos due to being such a despicable character. He has coolhair, that seem to be made of fire. And his armor?? Man, best armor in the franchise!
Jack of Blades from Fable may murder your mother and blind your sister among other things. However, being one of the few well-voiced characters in the game, the first Big Bad in the series, and just generally an all around badass Humanoid Abomination/Eldritch Abomination, he earns this status. He easily ranks as the best villain in the series.
As evil as they are, you have to admit the Reapers from Mass Effect are pretty cool. They're unfathomably advanced squid-shaped spaceships with apparently no desire beyond killing everyone every few thousand years because, hey, why not?
Through not exactly a villain at the moment(but perhaps will be a antagonist an X-Pack), the Knight Templar Angel Imperius from Diablo III seems to be heading in this direction given his badass armor design and the short but badass fight between him and Diablo at the beginning of Act IV.
General Tarquin earned himself fandom adoration for his affability and for being Dangerously Genre Savvy. He actually lampshades this trope, commenting that, "Audiences always think the villain is cooler than the hero is, anyway."
On a more or less literal example, sites like Something Awful and Encyclopedia Dramatica took off on and later propagated the idea that e-baggery is hip and whoever feels empathy for others is not a true nerd.
While calling him evil is a bit of a stretch, Strong Bad of Homestar Runner was originally intended to be a bumbling bad guy who always lost. He quickly became the most popular character on the website. His old introduction video actually said "you don't know it yet, but I'm the real reason you're here." From the first Strong Bad Email: "Do you use [your powers] for good, or for awesome?"
Generally, this is the point of Eric Cartman from South Park, especially as The Coon from the "Coon & Friends" trilogy.
Senor Senior, Senior was just a bored billionaire until Ron gave him the idea that it would be really cool if his mansion were an actual supervillain lair.
Ron often parodies this trope when faced with Deadly Invention of the Week.
Ron: That would be so cool if it wasn't going to hurt us.
Not to mention the episodes where he becomes evil. When this happens, he is quite possibly the most badass character in the entire show.
Mighty Max: the archvillain Skullmaster was voiced by Tim Curry. Luckily, for the rest of the cast, he only showed up in about 5 episodes. But in those episodes, well, he rules hell, and has demon and zombie armies at his command. Oh, and he can outsmart the Smart Guy and beat the Big Guy in a straight fight. Oh, and all of his convoluted plans succeed...except for the last one. Maybe.
Megabyte from ReBoot. While fairly average throughout the first season, in subsequent seasons, he became increasingly hardcore, with impressive plans and still enough time to hand the heroes' asses to them in occasional fights.
You're watching Futurama, the show that does not advocate the cool crime of robbery!
Blackarachnia is very popular amongst the fanbase — like she says, she's hot, poisonous, and deadly. (Also, a Femme Fatale with the sort of body most fanboys only get to look at, that might also have something to do with it.)
The villains always have cooler names. The Autobots have "Optimus Prime", "Bumblebee", "Ironhide", "Ultra Magnus", "Trailbreaker", "Cliffjumper", "Bulkhead", "Wheeljack", "Smokescreen", and "Blurr", but how do they compare with Decepticons "Megatron", "Starscream", "Devastator", "Demolishor", "Frenzy", "Bonecrusher", "Barricade", "Blitzwing", "Shockwave", "Skullcruncher", "Ruination", "Predaking" and..."The Fallen"?
Care Bears: for some older fans, the main villains of the Nelvana series and movies are more entertaining than the Care Bears and Cousins.
The Dreamstone falls under similar territory. The fanbase largely favors Zordrak and the Urpneys over the cutesy residents of the Land Of The Dreams. Granted, for the Urpneys, it may be more a case of "Evil Is Funny".
Similar to Xanatos and Slade above, Tombstone and Green Goblin, the two main Big Bads of The Spectacular Spider-Man, are perhaps two of the most awesome characters in a series full of them.
Who was your favorite character from Fantasia? If you responded anything but Chernabog, the towering demon on the mountain from the end of the movie, your pants are now on fire.
Victor Veloci, the villain of the horrifically Anvilicious and poorly researched Dino Squad, is seen by many of the show's few viewers as the only interesting character.
Zuko also managed to profit from this; considerably less since he's a) not that good at being evil and b) The Woobie even when he's evil, but it gave him a certain style and badass cred that seems to help draw in the fans. Especially in the beginning of the first season, when he was actually the villain.
And Fire Lord Ozai. Not the Magnificent Bastard his daughter is, though he sure seemed something like it until he completely lost his mind.
Amon from The Legend of Korra. He's voiced by Steve Blum and therefore has a deep voice that he uses in frightening threats, a cool and scary mask, doesn't flinch when fire blasts into the room he and his mooks are in (incapacitating them) and can resist the assault of a powerful rogue bloodbender, something only an equally powerful waterbender has been shown to do. Finally, he absolutely terrifies Korra. A guy who claims to be a non-bender manages to terrify the most powerful bender in the world. Just as she's starting to get her confidence back, he ambushes her and delivers a Breaking Speech so effective that she breaks down into tears afterwards. He achieved true Magnificent Bastard status in record time. It took only six episodes to achieve it and he's only had a major part in THREE!
His Mooks, the chi-blockers, also count. Not only do they look cool, but are also some of the most competent and dangerous mooks ever put into Western Animation. They're like an army of Elite Mooks. Two of them can put up a strong fight against two very powerful benders.
An in-universe example: in one episode of The Simpsons, Bart dismisses the entire genre of Christian rock because "everyone knows the best rock groups are affiliated with Satan."
In Rango, this is pretty much the reason behind Rattlesnake Jake's popularity. The Rule Of Cool runs very high for him; he's a black hat rattlesnake western outlaw modeled after Angel Eyes, he weaves words of hellfire and damnation into his speech (which is provided by Bill Nighy), and has a Gatling gun grafted onto his tail. He's Creepy Awesome and Crazy Awesome all rolled into one!