Villainous Friendship

Proof that two wrongs can just feel right.

"Sardu and Ralphus have a... special relationship. Sardu doesn't spend the movie yelling at him or belittling him like in movies such as The Body Shop, in this one it... seems like they're friends."

The relationship between the Big Bad and The Dragon is...complicated. Sometimes The Dragon has different goals in mind than his boss. Sometimes the Big Bad will toss aside his Dragon without a second thought should he fail his master, or cannibalize him for an extra power boost. Sometimes The Dragon only follows the Big Bad out of loyalty or duty. Sometimes they even intend on stabbing him in the back. It would seem that the relationship between the two positions varies from grudging respect to deep loathing.

But what if the two are actually friends?

It's not too much of a stretch, when you think about it; who does the Big Bad always have at his beck and call to talk out his issues and hang out with? His Dragon. After spending so much time together, the two may form some kind of a bond, whether it's just a matter of Emperor Nefarious wanting to know how Zartok the Destroyer's wife and kids are, or if the two are True Companions, sticking out for each other to the end. Neither one necessarily has to be a good person; sometimes they're both Affably Evil, other times the Big Bad cares nothing for any of his troops except for his right-hand man. This relationship often comes in two varieties: either they both care for another, or the relationship is only one way.

Compare My Master, Right or Wrong, Even Evil Has Loved Ones, and Unholy Matrimony when the relationship is romantic. Contrast The Starscream. May result in Moral Myopia if they condemn heroes for doing the same things as themselves. For characters who don't get along, it's Headbutting Heroes.


Examples:

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    Anime and Manga 
  • The Pillar Men from JoJo's Bizarre Adventure Part 2 have known each other for millennia; it's no surprise they like each other (except for Santana, who the others see as kind of a weak tool). Esidisi was even willing to sacrifice his life so that his comrades' plans could succeed.
  • Some of the Akatsuki duos in Naruto end up like this, but the most obvious are Konan and Nagato, who were actually friends prior to joining Akatsuki, and as such are actual friends instead of being forced to work with each other.
  • Guame and Lordgenome in Tengen Toppa Gurren Lagann. Supplemental materials show that Guame was once Lordgenome's Non-Human Sidekick (as Boota is Simon's). A thousand years of ruling the planet has warped both of them, but they are still on better speaking terms than Lordgenome is with anyone else.
    • To put it in perspective, the other three generals are afraid of reporting failure to Lordgenome because they know it might mean their lives, whereas Guame can get away with openly questioning his orders in front of the others.
  • Gundam:
    • Played with in Mobile Suit Zeta Gundam. Sociopathic Soldier Yazan Gable is clearly incapable of showing empathy or actually caring about anybody. But it's just as obvious that he enjoys the company of likeminded psychopaths Dunkel Cooper and Ramsus Hasa and Big Bad Paptimus Scirocco, playing the Manly Man to the latter's Sensitive Guy.
      • Sarah Zabiarov is shown to have a bad case of hero-worship and/or heavy crush on Scirocco, which he naturally exploits whenever necessary. However, there is a hint that Scirocco may have cared for Sarah more than his other pawns, as when she dies, he completely loses control and goes ballistic, the only time in the series he does so.
    • Mobile Suit Gundam SEED Destiny reveals that Big Bad Gilbert Durandal had a functioning friendship with his predecessor, Rau Le Creuset. In fact, most of Durandal's actions are driven by his inability to prevent Le Creuset's spiral into madness.
  • In Yu-Gi-Oh!, Marik's relationship with Rishid (his foster brother as well as his second-in-command) is complicated. The two are very close, and Rishid does show Undying Loyalty to his brother, but this is for a very good reason: Rishid knows that he is the only one preventing Marik's even darker personality (who killed their father) from taking hold. When Yami Marik does eventually take over, he tries to kill Rishid to prevent the real Marik from regaining control, but Rishid refuses to desert the real Marik, and this plays a vital role in the Final Battle between the villain and the Pharaoh.
  • Reiner Braun and Bertolt Hoover from Attack on Titan are devoted friends, and make for an extremely dangerous team as a result. They are fiercely protective of each other, and won't hesitate to risk their own life to help the other. Their friendship with their aloof partner, Annie Leonhart, is a bit more complicated. Even more complicated is their friendship with the other members of the 104th, who they genuinely consider their friends regardless of being on the opposite side of the conflict.
  • The Team Rocket Trio of Jessi, James, and Meowth from Pokémon. They genuinely care about each other and their Pokémon. In one episode it was shown that Meowth was not treated well by them. In almost every other episode however, they treat him as a true friend.
  • The Power of Friendship is so strong in Kinnikuman that even villains express it. This is especially notable in the case of Ashuraman and Sunshine during their fight with the Hell Missionaries. Ironically, they had spent that arc actively blocking the Power of Friendship from aiding Kinnikuman.
    Sunshine: It doesn't matter if we're devils! I can't abandon the person who's fighting this battle beside me to the very end!
  • In Eyeshield21, Blood Knight Gaou genuinely respects and considers Marco to be his friend and role model, even if Marco himself is openly terrified of Gaou.
  • In Hunter x Hunter, Hisoka and Illumi hang around each other quite a bit during the Hunter exams and the chairman election arc, trading information, having casual chats, and helping each other with their plans.

    Comic Books 
  • The Incredible Hulk give us Abomination and The Leader, who became friends through their mutual hatred of the Hulk. Leader was even upset when the Red Hulk killed Abomination.
  • In as much as either of them is capable of it, Lex Luthor and The Joker are friends. They understand one another better than any other villains do, and despite their many fallings out, they'll always work together again.
  • The page image is a variant cover from Sonic the Hedgehog/Mega Man: Worlds Collide, where Dr. Eggman and Dr. Wily start the Crisis Crossover because they find a mutual friend and kindred spirit in one another. The partnership works out very well up until late in the series: the stress of their failure to stop Sonic and Megaman, despite their teamup, combined with the fact that Dr. Eggman is a murderous psychopath who will casually throw Dr. Light to his death from their vessel once he decides Dr. Light is too dangerous to keep alive, which offends Dr. Wily because A: he considers that going too far and B: he wanted to keep Dr. Light alive to rub his triumph in Light's face, causes an irreconcilable break-up between the villains. They promptly start double-crossing each other and further ruin their efforts to stop Sonic and Megaman.
  • Poison Ivy and Harley Quinn are genuine friends.
  • Black Tom Cassidy and the Juggernaut were friends for many years. Wolverine once teased Juggernaut by referring to Cassidy as "your boyfriend". Juggernaut once dived underwater to save Cassidy from drowning. For Cassidy's birthday, Juggernaut once gave him the Crimson Gem of Cyttorak, hoping to give him some of his powers. After Juggernaut's Heel-Face Turn, he convinced Cassidy to turn himself in.
  • Greg Rucka's run on The Punisher introduced Stephanie Gerard and Christian "Chris" Poulsen. Stephanie's a former AIM scientist who wants to get into regular crime because it is more profitable and less risky. Chris is a former SHIELD operative who acts as her right-hand man, confidante, and muscle. The two share a genuine friendship, spend all of their time together, and at the time of Stephanie's death, were moving towards a romantic relationship. When she dies at The Punisher's hands, Chris proceeds to go on a Roaring Rampage of Revenge that sees himself dead, leaves a double-digit bodycount, and results in The Punisher becoming the NYPD's Public Enemy #1.
  • Hierarchy members Sere and Emeris in A Distant Soil have a reasonably close friendship based on their common fondness for Torture for Fun and Information, murder and Mind Rape. Emeris doesn't mourn long (or at all) when Sere is killed though.
  • The Flash's archenemy Captain Cold has a surprisingly strong friendship with fellow villain Heat Wave. All of the Rogues like each other to some extent (except Captain Boomerang) but Cold and Heat Wave are especially notable in this regard. They constantly bicker and have completely opposite motifs and personalities, but are also very protective towards one another and Captain Cold is genuinely concerned about Heat Wave's ever-damaged mental state.
  • Red Skull has a incredibly loyal second-in-command in the form of Crossbones. Crossbones is the only person who genuinely likes and looks up to Skull, considering him a mentor-figure. No matter what atrocious act Red Skull commits, Crossbones will always be there to help him. It helps that Crossbones is also hopelessly in love with Red Skull's daughter Sin.
  • Dr. Doom has one with his right hand man Boris. Boris is highly loyal to the doctor. Doom seems to care for Boris as well, being content to leave him in charge of Latveria whenever he is away. Doom even acknowledges Boris as his "only living friend".

    Fan Works 
  • In Mega Man Reawakened, Glyde and Bass are friends, and later, so are Glyde and Wily. Glyde even paid Wily's billion dollar bail.
  • Neomorphs: The Visser and Guraff are close friends, and appear genuinely concerned whenever the other is in danger.
  • In The Lion King Adventures, Timon and Pumbaa are turned into evil beings who drain the souls of cubs to preserve their immortality; however, they are still just as much friends as they were in the actual films.
  • In The Moon's Apprentice, Nightmare Moon legitimately appears to care for her dragon, Twilight Sparkle, although when she began to care is up for debate.
  • Vengeance of Dawn has the eponymous fallen heroine Breaking Dawn and her circle of foalhood friends, Razor Wind, Cherry Blossom, Hardy Bloom, Laurel, and Hard Candy. None of the latter five are particularly evil, but go along with Dawn's plot to dethrone the newly-crowned Twilight Sparkle and win back the favor of Princess Celestia, simply because their loyalty to her is so strong. She feels the same way toward them, as seen when she promises not to leave them behind when she becomes a princess of Equestria. In fact, one could make the argument that they're as close as Twilight and her friends are. They don't even abandon Dawn when her plan fails and the princesses come to arrest her, sticking by her side until the end. How's that for loyalty?
  • In Child Of The Storm, it's been noted that Gravemoss and Dr. Zola get along disturbingly well.

    Films — Animated 
  • Maybe they're a bit more like pets, but when Ursula accidentally zaps Jetsam and Flotsam in The Little Mermaid, she looks absolutely distraught and decides to go One-Winged Angel.
  • Although Iago does take a few blows along the way, he and Jafar seem to have a genuine friendship throughout Aladdin. They chat pleasantly with one another, Jafar actually takes advice from him at one point, and even after he conquers Agrabah he keeps Iago at his side to enjoy in the spoils as well. You can pretty much consider it fizzled by the end, though.
  • Care Bears Movie II: A New Generation begins with the villain, Dark Heart, blackmailing a girl named Christy after a Deal with the Devil. Partway through the movie, however, she saves him from drowning, which begins to make him actually care about her. This eventually leads to a Heel-Face Turn that makes him Become a Real Boy.

    Films — Live-Action 
  • Humperdinck and Rugen were portrayed this way in The Princess Bride, with full on Affably Evil, Heterosexual Life-Partners overtones.
  • In The Dark Knight Rises, it is revealed that Bane is merely The Dragon to the real Big Bad, Talia Al Ghul. Their backstory swiftly reveals that he pledged his life to protecting her when she was a little girl in a Hell Hole Prison, and it's likely that Talia is the only person Bane has ever cared about, to the point that he was willing to fight off almost all of the other inmates, suffering an agonising disfigurement in the process, just so that she could have the freedom that was denied to him. And she came back for him, bringing the might of the League of Shadows to bear against the prisoners who injured Bane and murdered Talia's mother, asking Ra's to spare Bane. Their relationship has been one of absolute loyalty and mutual trust ever since.
    • In The Dark Knight, the Chechen and Maroni are clearly good friends outside of work. They're even having dinner together when they're arrested.
  • Calvin Candie and Stephen in Django Unchained are shown to be genuine friends, with Stephen, the head house-slave, preserving Candie's authority at Candieland and basically running his plantation for him, and Candie providing Stephen with a dominant position in his organization.
  • Cohaagen and Hauser (Quaid's former identity) in Total Recall (1990). Cohaagen acknowledges their friendship when Quaid calls the guy an asshole and makes sure he is given an obedient, mindwiped wife to "enjoy", goes into a rage when he is forced to order the death of his friend, and goes on a tirade against Quaid for making sure he's not coming back.
  • In Scarface (1983), Tony Montana and his eventual Dragon Manny Ribera start out the film as friends, which doesn't change as they start a criminal empire in Miami. Manny eventually gets fed up with Tony's more malicious behavior, like beating up his sister's touchy boyfriend. When Manny secretly elopes with Tony's sister, his friend goes nuts and kills Manny in a jealous rage.
  • Drug kingpin Nino Brown in New Jack City has a friendship with his lieutenant Gee Money that doesn't seem to be faked. When they establish their criminal empire, Nino tells Gee that they've finally made it and that they have to look out for each other. Near the end, he expresses his friendship with Gee as more important to him than all the money and women he has gotten, but they just can't go back to the way they were after Gee betrays Nino by making a deal behind his back. Nino struggles to kill Gee as tears roll down his face.
  • Gothika: The serial killer/rapist is eventually revealed to have had an accomplice. After Sherrif Ryan is revealed as Doug's accomplice, he states that he helped Doug out with his first kill because they were friends, and since then they have been destroying countless lives for their depraved gratification. Ryan goes on a rampage against Miranda as revenge for killing Doug (she was possessed by the ghost of one of the victims).
  • In the first Batman film, directed by Tim Burton, The Joker and his right-hand man Bob seemed to have a pretty good relationship. Bob was the second in command of The Joker's group of thugs back when he was Jack Napier. After Jack's transformation into The Joker, Bob stayed by his side as his loyal right hand man. Bob was very loyal to his boss and did everything he was asked with a "Yes sir!" The Joker seemed to value his loyalty pretty well, telling him "you are my number one guy". But that all ended when The Joker shot and killed Bob just to vent his anger after Batman foiled one of his plans.
    • Riddler and Two Face from Batman Forever get along great and seem to be having the time of their lives in every scene they share. Even when Two Face and his goons crash Riddler's party, he simply complains that Two Face should have let him in on it.
  • Harry and Marv from the Home Alone films seem to have a pretty good friendship, despite Harry often getting annoyed with Marv's stupidity. In a deleted scene, the two are even shown singing "Harry And Marv are coming to town".
  • In Hellboy II, Prince Nuada was heartbroken and enraged at the death of his sidekick Mr. Wink, telling Hellboy "You will pay for what you did to my friend back there".

    Literature 
  • Implied to be the case between Nicodemus and Anduriel, the Fallen Angel that shares his body, in The Dresden Files. While most of the Denarians (the organization Nicodemus heads) end up little better than slaves to their Fallen before long, the fact that Nicodemus has retained his free will and humanity despite being possessed for approx. two thousand years speaks of at the very least a healthy respect between them. Part of the reason it works is that Nick is horrible enough on his own that he doesn't really need much demonic prompting...
  • In the Honor Harrington series'', Rob Pierre and Oscar St-Just are friends aside from being loyal, while they recognize they are two very different personalities. David Weber often shows this type of relationship between people on the opposing side of his heroes, as he often has the "villains" be doing things for reasons other than just purely For the Evulz.
  • In Twilight Sparkle and the Crystal Heart Spell, Trixie and Gilda are shown to have met each other and become friends at some point. The two have fun pulling pranks and scamming ponies. It is an Odd Friendship because Gilda hates ponies and Trixie IS a pony.
  • Belch is this to Henry Bowers in It. Villainous jerk or not, it takes a pretty brave and loyal guy to stand up against a fricking Frankenstein's monster just for the sake of protecting a friend. Henry barely returns the sentiments, though he does apologise to Belch's reanimated corpse (though it's actually the creature in disguise) for leaving him behind to die.
  • In the prequel novel Wolf Creek Desolation Game: Mick Taylor is shown to have had one with his superior during the Vietnam War, Sergeant Atkin. The two raped and tortured women together. During a mission, Atkin taught Mick the "head on a stick" technique, and watched as Mick cut a soldier's head off, and mount it on a pike. The two seemed to like each other and get along quite well. Their friendship ended when Atkin decided to try and kill Mick to make sure he didn't talk about what they did.

    Live Action Television 
  • In season 3 of The Vampire Diaries, Stefan and Klaus, but it's more like "comrade"ship than friendship.
  • Tony Soprano of The Sopranos with Silvio Dante and Paulie Gualtieri.
  • Avon Barksdale and Stringer Bell from The Wire have been friends since they were kids, and as of the show's first season they have killed and plotted their way into controlling the drug trade on the West Side of Baltimore. However, they begin to grow apart after the end of Season 1, when Avon is arrested and sent to jail while Stringer avoids any jail time, as Stringer has very different ideas about running the business. Stringer wants to run the illegal drug trade like a business, without the violence and Mob Wars, while Avon exults in everything that is part of The Game, especially his reputation and the taking of turf. Eventually they both reluctantly turn on each other, with neither knowing that the other was also doing a set up. The result is that at the end of Season 3 Stringer dies and Avon goes to jail again.
  • Justified has Wynn Duffy and his bodyguard and enforcer, Mike, who live together in Wynn's trailer, and always look out for one another. There's also Dickie Bennett and Dewey Crowe, who are always overjoyed to see each other, and go out of their way to protect one another when in jail together.
  • Roose Bolton and Walder Frey are seen amicably chatting and bantering back and forth the morning after the Red Wedding in Game of Thrones, celebrating their ascensions and the destruction of House Stark and House Tully.
  • Sado and Yuko in Majisuka Gakuen
  • Elias and Scarface in Person of Interest. From their first moment on screen together, it's clear that they're closer than your standard boss and minion; as the series goes on, we see them sharing a nice meal together when one of the good guys comes calling, and when Scarface is gunned down when Elias is in jail, Elias has his bodyguards paroled to watch over Scarface in hospital. It turns out they met as kids in an abusive group home, and are the closest thing each other has to family.
  • Daredevil; Wilson Fisk and his Dragon James Wesley. Beyond acting as his head enforcer, Wesley helps Fisk woo the woman he loves and encourages him to do things that make him happy. In return, Fisk speaks fondly of Wesley and even gives him a genuine "Thank You" for everything he's done. Fisk takes it really badly when Wesley is gunned down. by Karen Paige.
  • Buffy the Vampire Slayer:
    • In S2, Spike and Drusilla are a genuinely loving couple. When The Judge, a being designed to destroy all humanity rises, he states that their love for each other means he could kill them easily despite their not being human.
    • In S3, Mayor Wilkins loves his Dragon Faith like a daughter. Hurt one and the other will come looking for you.

    Professional Wrestling 
  • Brock Lesnar and Paul Heyman. Despite being Heels, the two do genuinely care about each other. In the 2013 Extreme rules match against Triple H, when Trips had Brock in a submission he had no chance of escaping, Paul rushed into the cage to help Brock knowing that he stood no chance against Trips, allowing Brock to defeat him. In one interview, Heyman described a meeting with Brock where Brock showed him a picture of their kids playing together. Lesnar was also the one who asked Heyman to be brought back to the WWE.

    Tabletop Games 
  • The Pathfinder adventure path "Legacy of Fire" posits a close friendship between gnoll assassin Rokova and troglodyte cleric Grundmoch, despite the fact that both of them are Chaotic Evil servants of Rovagug. This actually becomes a plot point, for when evil genie Zayifid kills and replaces Rokova, Grundmoch notices, outs the genie to the PCs, and is actually quite willing to ally with them if it means Zayifid ends up dead. A Spanner in the Works caused by friendship between monsters. Not something you see everyday.
    • Grundmoch actually seems to have a talent for this. His personal bodyguard is a gibbering mouther called The Gargler, which the text notes he has managed to not only train, but befriend. The Gargler is loyal to Grundmoch, and will attack anyone who threatens him without any regard for its own safety.
  • Vampire: The Masquerade: Granted this is enforced more by collective blood bond (and a healthy dose of brainwashing/conditioning/Stockholm syndrome), but Sabbat packs tend to have this by default. It's a magically enforced friendship, but such Cainites will eagerly face Final Death for each other. It's those in the Camarilla that have a hard time standing each other. In fact, while regular, unenforced friendship is possible (there are clear examples of this, foremost being the coteries), it's heavily implied to be against Kindred nature as a whole. Ironically, it's the bad guys (or worse guys) that are most likely to employ the Power of Friendship. Unless they're the player characters, of course.

    Video Games 
  • Bahamut Lagoon has Sauzer (Big Bad) and Palpaleos (The Dragon), who have been friends for a long time.
  • In the Castlevania series, several manuals/bestiaries claim that Dracula and Death are this. Sadly, aside from Portrait of Ruin and possibly Lament of Innocence, protagonists rarely see this in action.
    • It should be noted that even though Dracula does use Soul Steal on Death once (in the aforementioned Portrait of Ruin), Death told him to do it as a last-ditch effort to defeat Johnathan and Charlotte.
  • Touhou: Toyosatomimi-no-Miko and Mononobe-no-Futo, the scheming immortals.
  • Shezar and Mudou in Duel Savior Destiny tend to fight a lot and threaten to kill each other, but considering their personalities, the fact that they haven't done it is a pretty good indication of their friendship. When Mudou dies before Shezar in Mia's route, he's the only one of the bad guys to actually get upset about an ally falling while the rest of them basically shrug and call him replaceable.
  • Hazama and Relius from BlazBlue seem to be pretty friendly with each other, despite both of them being head-screwing world-exploding sociopaths that are the cause of almost everything wrong in the world for the last century or two. Heck, it's implied that being such big assholes actually helps them get along. The reality is much muddier, as Relius' Astral quotes in Chronophantasma express increased frustration at having to rein Hazama in, and Terumi (Hazama's alternate personality) has a victory quote stating he always hated Relius' guts. Little wonder Relius gets horribly broken and Hazama comes down with a sudden case of death by the end — they were so confident in their ability to rein in the heroes and the Imperator that they started letting their true colors slip.
  • Gym Gingnham, psychopathic Blood Knight Big Bad of Turn A Gundam and depraved rapist Psycho for Hire Yazan "I'm gonna violate you" Gable of Zeta Gundam fame become fast friends when they meet up in Dynasty Warriors: Gundam.
  • The demons Decarabia and Forneus of the Ars Goetia aren't mentioned in the original text as having any relationship to each other, but are best friends in two out of five the Shin Megami Tensei games in which they both appear, even getting a combination attack together in Persona 3. Probably because, again unlike in the Goetia, they're both depicted as sea creatures, a starfish and a ray respectively.note  It more or less started in Shin Megami Tensei III: Nocturne, where Decarabia's found waiting for Forneus at the site of the Hachiko statue.
  • WildStar has the Draken and the "Chua." The former love killing things. The latter dedicate their lives to making better, more efficient ways of killing things. They got along nicely.
  • Cassius and General Gaius in Dust: An Elysian Tail were evidently close friends and shared the same vision of the future. For this reason, he doesn't order Dust's death, and the final fight has Gaius pleading with Cassius to remember.
  • Albert Wesker and William Birkin from Resident Evil, at least as much as two sociopaths could be. Placed in charge of one of Umbrella's facilities as teenagers, the two were noted to be close and conspired together on many occasions. Their partnership remained well into their 30s, with Birkin actively aiding in Wesker's plan to betray Umbrella and steal their research. Birkin's death at the hands of Umbrella agents seems to have genuinely made Wesker very cross, something rare for a man infamous for using and throwing people away.
  • Ellen and The Demon from The Witch's House share a... complicated relationship. On one hand, they seem to mostly be working toward their own goals, Ellen often gets annoyed with The Demon, and he is willing to pull a You Have Failed Me on Ellen. On the other hand, they do seem to get along over their shared love of evil, and The Demon usually greets her in a friendly way, often addressing her with a "Yo". In one of the game's endings, he addresses Ellen as "My fair witch", he taught her how to read and write, and instead of pulling a You Have Outlived Your Usefulness he kept his part of their deal.
  • In Pokémon Alpha Sapphire, this seems to be the case between Archie, the Team Aqua Leader, and his Perky Female Minion Shelly. In the Aqua hideout, Archie had a photograph of him, Shelly and Jirachi taken approximately twelve years agonote ; He seems to be close to Matt too, who sees him as a brother. This is in stark contrast to Maxie of Team Magma in the other game, who doesn't seem to care at all about the female Admin and accuses his Dragon of trying to usurp the position of leadership (when what the guy's true intent is to prevent the terrible mistake Maxie is about to make).
  • Lex Loathe and Glyde are damned near inseparable in The Misadventures Of Tron Bonne with the latter even jokingly mocking the former's utter lack of morals which they both laugh over. This carries over to Mega Man Legends 2 (where it's implied Lex is dead), where Glyde still keeps his portrait in his flag ship.
  • In Warcraft III, the death knight Arthas and the lich Kel'Thuzad have a very real camaraderie throughout the Undead campaign. Their bond grows so close, and they grow to trust each other so much, that it's easy to forget that Arthas actually killed Kel'Thuzad when they were respectively still a paladin and a necromancer. Or that they're both agents of a vast undead army whose sole purpose is to eradicate any and all life on the planet.

    Web Comics 
  • Homestuck: Jack Noir and the Draconian Dignitary, as seen here and the next page. They seem to actually be Moirails (compare with the definition of Moirallegiance here).
  • Goblins has Dellyn Goblinslayer and his dragon Sarral Caine, two evil adventuring buddies who've been through thick and thin together. Dellyn considers Caine to be the only person around that can be depended on, and is visibly shocked and grief-stricken when he finds Caine's body.
  • The Order of the Stick:
    • Xykon and Redcloak show a veneer of this, laughing together over tormenting heroes and minions. In fact, Xykon is callously abusive towards Redcloak, while Redcloak sees the undead Xykon as nothing more than a powerful tool that he tries to manipulate to his own ends. The Monster in the Darkness thinks of the rest of Team Evil as his friends, but they very obviously do not reciprocate.
      • Tsukiko firmly believes that she and Xykon are friends, allies, and soon-to-be lovers. Xykon sees her as an expendable pawn and is indifferent when Redcloak feeds her to her own wights.
    • Tarquin and the Vector Legion appear to be a straight example: their ploy to conquer the Western Continent ran on decades of cooperation and respect. In particular, Tarquin refers to Malack as his best friend, and murders his son Nale in chilling Tranquil Fury when Nale kills him. Laurin's reaction to Malack's death suggests that she was also fond of him.
      • Miron is friendly enough with Tarquin to nickname him Tarkie, and chats with Laurin about her daughter's plumbing business.
    • Thog sees Nale as a friend, though Word of God is that Nale keeps Thog around for his combat ability and has no real concern for him. Nale and Sabine would be a straight example, but have edged into Unholy Matrimony.
      • Nale and the drow wizard Zz'dtri seem genuinely friendly and show surprising loyalty towards each other. Nale is genuinely horrified when the latter is killed, even trying to save him before being forced to flee.
    • Back when he was a young human, Xykon had a genuine one with fellow apprentice Yydranna. He accepted her being chosen as their boss's Dragon over him, she gave him advice about his tendency to go with raw power over tactics, and they parted on pretty good terms for mass-murderers.
    Yydranna: If I'll ever see you again, I'll have to ruthlessly crush you.
    Xykon: I'd be disappointed if you didn't try.
    • Redcloak and the Hobgoblin General also seemed to be on good terms, but he died before we knew his name, so...
    • Goblinoid clerics Redcloak and Jirix have, like, the only genuine and loyal comradeship Redcloak's had with anybody since his brother died years ago.

    Web Original 
  • While Moist in Dr. Horrible's Sing-Along Blog arguably qualifies as Horrible's Dragon more just by default than anything, the two are clearly best friends as well as supervillain and (only) henchman.
  • Rich Burlew (author of The Order of the Stick) wrote an article on giving TTRPG villains personalities that extended beyond acting purely to further the plan. The example he gave was a campaign in which two villains who were working together and whom the heroes fully expected to backstab each other, because they just couldn't believe that the villains really were best friends.
  • In The Irate Gamer, Evil Gamer and Satan seem to be pretty good friends. In the Zombies Ate My Neighbors review, Satan and Evil Gamer were shown having a friendly conversation in Hell, and Satan even agreed to bring Evil Gamer back to life. In the Monster Party review, Satan and Evil Gamer made a deal where evil would help Satan get to Earth so he could Take Over the World if Satan killed the Irate Gamer. Satan ended up befriending Irate Gamer instead and went to hang out with him and Ronnie at a bar. Evil got mad at Satan for not killing the Irate Gamer, but Satan suggested that they all Go-Karting with Bowser, even offering to get Evil Gamer some cheesecake. In the Silver Surfer review, Satan congratulates Evil Gamer for thinking of a robot invasion before he did.
  • In Worm, when Skitter takes charge of the Undersiders, either Tattletale or Bitch could count as The Dragon. In both cases, Villainous Friendship is in play. Also, both cases are due to their own Crowning Moment of Heartwarming.
  • Marik and Yami Bakura from Yu-Gi-Oh! The Abridged Series have a strained but ultimately prevailing friendship throughout much of the series. Of course, they may have only gotten this far because Bakura's still holding out for something else.

    Western Animation 
  • Christy and Dark Heart in Care Bears Movie II: A New Generation, due to a Deal with the Devil, that eventually leads to Love Redeems.
  • He-Man and the Masters of the Universe (1983): Seen with some of Skeletor's henchmen, oddly enough. It's most obvious with Trap-jaw and Whiplash's friendship (which comes across as Whiplash having a rather one-sided boy crush on Trap-Jaw), but Trap-Jaw seems to be pretty chummy with Beastman too (of all Skeletor's henchmen, the two are the most likely to appear as a duo), and Webstor and Kobra Khan seem to get along quite well also. Tragically, I don't think we'll ever know how Khan really felt about his Snakemen buddies killing Webstor in the 2002 series.
  • The Psycho Rangers in the third season of The Legend of Korra all get along very well. Zaheer and Gahazan give each other a firm handshake upon meeting each other again (and friendly chatter on how Zaheer gained airbending following Harmonic Convergence), Ming-Hua light-heartedly teases their "ugly mugs" but is very grateful to see them when they spring her, and jokes about how they rescued her before Zaheer's girlfriend.
  • Megatron and Soundwave of the various Transformers franchises definitely qualify. In fact, when reborn as Galvatron, Megatron showed open grief and rage at Soundwave's death, and cared enough for him to bring him back to life.
  • Transformers Prime has Breakdown and Knock Out, The Brute and the Deadly Doctor respectively, who are in fact extremely good friends. Knock Out takes Breakdown's demise and Silas' use of his corpse as a cyborg body very, very badly. Knock Out and Starscream also qualify, since they share a mix of Evil Genius, Butt Monkey, and Dirty Coward traits and easily sympathize with each other as intelligent but rather histrionic villains.
  • While not exactly "villains", Diamond Tiara and Silver Spoon of My Little Pony:Friendship Is Magic are two friends who love to bully and antagonize the Cutie Mark Crusaders, and they are always antagonists in episodes where they play a role.
  • Pinky and the Brain are Well Intentioned Extremists trying to Take Over the World to make things better. Pinky obviously cares a lot about Brain, viewing him as a true friend. Brain often gets annoyed with Pinky and harms him, but despite this, he does in fact care about him. When Pinky sold his soul to get Brain the world in "A Pinky And The Brain Halloween", Brain rescued him because he missed him and ruling the world was no fun without him. In the Christmas episode, Brain tears up when he finds out that Pinky wrote a letter to Santa asking for Brain to be given more respect.
  • Spliced: Mister Smarty Smarts and his minion Octocat are often annoyed and frustrated by each other, but they're there for each other when it counts, as shown in the ending of "Octocataclysm".
  • Depending on the Writer, the League of Super Evil can be Vitriolic Best Buds or uneasy allies ready to betray each other at a moment's notice.