Villainous Friendship

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. 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 comes in three flavors.

Type I: The Big Bad and The Dragon are truly the best of friends, with complete trust and devotion between the two. Their relationship can range from True Companions to Heterosexual Life Partners to perhaps even something deeper. The two truly care about each other's well-being, and both look out for the other. If The Hero threatens the Big Bad, then you can bet that The Dragon will be right around the corner to smash his face in. And should The Hero seriously injure The Dragon (or, heaven forbid, actually kill him), the Big Bad will quickly lose his stoic Smug Snake persona and come after The Hero with Unstoppable Rage. In the case that The Dragon isn't a person but rather a creature under the Big Bad's employ (say, for instance, an actual dragon), the Big Bad treats him with care and respect, and in return The Dragon protects him with undying loyalty and ferocity.

Type II: The Big Bad cares deeply for The Dragon, but the Dragon couldn't care less for the Big Bad, either feeling neutral for him or outright despising him. This can result from The Dragon being forcefully given his position and/or power by the Big Bad, while the Big Bad cares enough for their well-being.

Type III: The Dragon cares about his master, but the Big Bad couldn't care less about The Dragon. This can sometimes result in My Master, Right or Wrong, when The Dragon shows undying loyalty to the Big Bad without the latter worrying about his fate whatsoever. The Dragon may die valiantly fighting The Hero in his lord's name, but the Big Bad will just be disappointed that his best fighter is down.

Compare My Master, Right or Wrong, and Unholy Matrimony when the relationship is romantic. Contrast The Starscream. May result in Moral Myopia.

Anime and Manga

 * In a filler arc of Bleach, is a Type III towards.
 * In Code Geass, the Emperor Charles and are Type I, as well as Cornelia with Guilford and Dalton.
 * Considering that pretty much everyone from Death Note is villainous in some way, there's a lot of these. Sit down, this will take a while.
 * Light and Misa begin as Type III, though seeing as, it is possible that they moved to Type I territory (though knowing Light, it's highly unlikely).
 * Misa and Rem are Type III; Rem cares deeply for Misa, but Misa doesn't really care about Rem.
 * Mello and Matt are Type I, seeing how Matt is.
 * Mikami and Takada are Type I, but
 * Light and Takada are very much Type III.
 * Light and Mikami are Type I. Mikami
 * A diagram in the databook actually implies that Light and Mikami are more of a Type III: Mikami is honestly loyal to Light, but Light views both Mikami and Takada as murderers who aren't that much better than other criminals. He does, however, think that Mikami is useful.
 * Light and Ryuk, on the other hand, are a subversion: Light seems to see Ryuk as a buddy to brag to, and Ryuk likes playing with Light, but in the end, Light only wants to use Ryuk as much as he allows it (e.g. making him find hidden cameras installed in his room ), while Ryuk just sees Light as a shiny new toy.
 * In the shonen manga Gamaran there's a Type III between Sakon Daimaru and his bigger brother Ryuugo. Namely, the mentally retarded Sakon sees Ryuugo as a loving big brother and mentor, while Ryuugo sees Sakon as a powerful human weapon and nothing else.
 * In Gash Bell, Zaruchimu is a Type III towards Riou, though grudgingly so; in his final moments, he reminiscences on how resurrecting Faudo with Riou felt like something grand, but when, it didn't seem worth it anymore, and he even ends up sobbing, trying to convince himself that he didn't think of Riou as his friend. However, it's possible that this was a Type I, as Zaruchimu states that, if he had fought together with Riou against Alishie and Umagon, that their teamwork would have prevailed; there's also the fact that the two don't share too many scenes together, and the only time their relationship is glossed upon is when Zaruchimu is thinking back as he's vanishing, so it's very possible that their friendship was true and went both ways.
 * Some of the Akatsuki duos in Naruto end up like this, but the most obvious are Konan and Nagato, who, and as such are actual friends instead of being forced to work with each other.
 * While Zabuza is really The Dragon to Gato's Big Bad, his own Dragon of sorts, Haku, shares a mutual respect and friendship with him that can be seen akin to a Type I Villainous Friendship.
 * In One Piece we have Gin and Don Krieg as a Type III, as well as Arlong and his crew as Type I.
 * 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.
 * Puella Magi Oriko Magica: Oriko and Kirika are either particularly devoted to each other, or Schoolgirl Lesbians.
 * Souten no Ken: Kasumi Kenshirou and Pang Kuang-Lin are the dearest Peng-You to each other.
 * Reiji Marco and Rikiya Gaou of Eyeshield 21 are a complicated example of this. Marco is the captain and quarterback/safety of the Hakushuu Dinosaurs, while Gaou is one of his two right-hand men; he's a colossal lineman whom Marco uses to break other players. Initially Gaou only seems to be working for Marco because it gives him the opportunity to hurt people, but as the series progresses, it becomes more and more obvious that he has a great deal of respect and admiration for Marco. At the same time, it becomes apparent that Marco is utterly terrified of Gaou, and he's honestly stunned when the latter expresses his respect for him aloud. By the end they seem to have moved into Type I territory though.
 * The American Pentagram are a collection of Jerk Jocks par excellence, and collectively, are nearly as bad as the Dinosaurs. At the same time, they honestly seem to like one another. This isn't surprising where Token Good Teammate Panther is concerned, but it's quite surprising when you add Mr. Don and Clifford to the mix. Clifford and Don in particular seem to be close; this might be why they make such a good Big Bad Duumvirate. In the backstory Shinryuuji's Agon and Deimon's Hiruma were sort of friends (as close to friends as someone like Agon can get anyway), but following Agon's betrayal of Hiruma and Kurita the relationship fell apart and has yet to be fixed.
 * Gundam Seed Destiny has a few examples. Big Bad Chairman Durandal and his Dragon, Rey Za Burrel share a very close father/son style relationship. Rey and Shinn Asuka also seem to share a Type I relationship, with the two of them being very good friends since their days in the academy (his friendship with Lunamaria Hawke doesn't really count because she is a Token Good Teammate). And, as flashbacks show, both Rey and Durandal shared a complicated friendship with previous Big Bad (and Omnicidal Maniac) Rau Le Creuset; the scenes with the three of them would indicate it was probably a Type I, and serve to humanise the otherwise monstrous Le Creuset. Durandal's entire motivation is his guilt over being unable to prevent Creuset's Sanity Slippage into omnicidal mania.
 * In Mai-Otome, a Type III exists with Nagi and Sergay. Sergay has long been loyal to Nagi, but Nagi often suspects Sergay of treachery, and after the Wham! Episode, only keeps him around to ensure his daughter Nina's cooperation..
 * In Mai Hime, a Type I exists between Alyssa and Miyu.
 * Played with in 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.
 * In Mai-Otome, a Type III exists with Nagi and Sergay. Sergay has long been loyal to Nagi, but Nagi often suspects Sergay of treachery, and after the Wham! Episode, only keeps him around to ensure his daughter Nina's cooperation..
 * In Mai Hime, a Type I exists between Alyssa and Miyu.
 * Played with in 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.

Comic Books

 * In all of the Marvel Universe, there's not a more perfect example of Type I than The Juggernaut and Black Tom Cassidy. They are so close that eventually, Wolverine couldn't resist the tempation to tease the Juggernaut by referring to Black Tom as "your boyfriend".

Film

 * Big Trouble in Little China depicts the Three Storms as being very loyal to the Big Bad to the point where, when the hero kills him, the last Storm becomes visibly upset and bulks up. An earlier scene implies that the Big Bad felt at least a certain amount of kinship with them as well so this could easily be a Type I.
 * Visibly upset to the points where their magic powers start to go wild.
 * Mad Max 2/The Road Warrior gives us a Type II, where the Humungus sincerely commiserates with Wez over the latter's dead boyfriend. Granted, it's in the context of a full nelson, but that still counts as sensitive by postapocalyptic biker-gang standards.
 * Humperdinck and Rugen were portrayed this way in The Princess Bride.
 * With full on Affably Evil, Heterosexual Life Partners overtones.
 * Megamind and Minion are Type I.
 * While there is lots of room for Alternate Character Interpretation, the hyena trio from The Lion King appear to be a Type I with each other (YMMV on whether Unholy Matrimony is also present).
 * The two girls in Beautiful Creatures.

Literature

 * Lord Voldemort gets very angry when his dragon, Bellatrix Lestrange, is . Still almost certainly a Type III, though his relationship with Bellatrix is about as close to love or friendship as Voldemort will ever get.
 * From Good Omens The demons Hastur and Ligur are Type I. Hastur gets really upset when
 * 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. Of course, part of the reason it works is that Nick is horrible enough on his own that he doesn't really need much demonic prompting...

Live Action Television

 * Perhaps done best in Damages in every season while always keeping it fresh. Season 1 featured the Big Bad Arthur Frobisher and his Dragon Ray Fisk, who were very close friends, to the point where . Likely a Type I.
 * Then there's a Type III in Season 2, Walter Kendrick couldn't care less about Claire Maddox, even though she gives her all in trying to save his company, to the point where she is kept in the dark about a case she was forced to take up.
 * Another case of Type I in Season 3, with the Tobin family as a whole and their lawyer, almost like family, Leonard Winstone. Though by the time of the final episode, the relationship isn't as close as it used to be...
 * Season 3 of Buffy the Vampire Slayer shows The Mayor and Faith as sharing a Type I relationship.
 * From fourth volume of Heroes Sylar and Luke are Type III, Luke hero-worships Sylar but Sylar doesn't really care about Luke
 * In season 3 of The Vampire Diaries Stefan And Klaus but it's more like "comrade" ship than friendship.
 * Type III-ish example in Nikita between Percy and Roan, his most trusted Cleaner. When Percy is imprisoned it's Roan who helps arrange his escape, and . It's uncertain, however, how Percy thinks of Roan, given how he sees Division as his pawns.

Tabletop Games

 * The Pathfinder adventure path "Legacy of Fire" posits a close friendship (Type I) 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 plotpoint, for when evil genie Zayifid kills and replaces Rokova, Grundmoch notices, outs the genie to the PC's, 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 totally loyal to Grundmoch, and will attack anyone who threatens him without any regard for its own safety. This is at least a Type III, though given how much Grundmoch seems to value the mouther, it may well be a Type I.

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.
 * Touhou: Toyosatomimi-no-Miko and Mononobe-no-Futo, the scheming immortals.
 * In the Sengoku Basara series, Toyotomi Hideyoshi and his dragon Takenaka Hanbe are a type I in the second game and anime (though Hideyoshi isn't very good at showing his side of it, making it seem like a type III), and Ishida Mitsunari and his dragon Otani Yoshitsugi are a very clear type I in the third game, with the two basically serving as each others' Morality Pets in spite of Mitsunari's No Social Skills and Yoshitsugu's Manipulative Bastard nature.
 * Akechi Mitsuhide is a very warped type III towards Oda Nobunaga throughout the series, loving the man and expressing it through the desire to betray and kill him over and over.
 * Albert Wesker and William Birkin seem to have had a genuine Type I and Odd Friendship in the backstory of Resident Evil.

Web Comics

 * The Order of the Stick: In the earlier strips, Xykon and Redcloak appeared to be a Vitriolic Best Buds example of Type I. However, as time has gone on, it's quickly become a total aversion, as they clearly despise having to work with each other, only doing so out of necessity.
 * Tarquin and Malack, meanwhile, appear to be a straighter example of a Type I.
 * Thog's relationship with Nale seems to be a Type III -- Thog explains to Elan at one point exactly why he thinks of Nale as his friend, but it isn't clear whether or not Nale actually likes Thog in turn or is just using him. At the same time, Nale's relationship with Sabine would be another Type I, if they weren't actually another trope.
 * Similar to the Thog/Nale example, the Monster in the Darkness' relationship with the rest of Team Evil appears to be a Type III. He definitely thinks of them as his friends, but they only tolerate him in order to use him as a secret weapon.
 * Redcloak does seem to have a genuine Type I with his own lieutenant Jirix -- even if they're not outright friends, they do have a healthy respect for each other, and definitely get along better than Redcloak does with Xykon.
 * 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).

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 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.

Western Animation

 * Megatron and Soundwave of the various Transformers franchises definitely qualify for a mutual Type I. 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.
 * Over in Beast Wars, Scorponok and later Inferno to Megatron for a Type III. Megatron is well-aware of their loyalty (something not to be taken granted for with bad guys in this franchise) and rewards them when they succeed, but doesn't hesitate to punish them for failure or even if they're just annoying him.
 * Shego/Draken in Kim Possible: Type II for the most part.
 * More a Type I really. In a Vitriolic Best Buds kind of way.
 * Pinky and The Brain are Type I or Type III.
 * Heinz Doofenshmirtz and Norm in "Phineas and Ferb" : Type III.
 * Lord Cyclonis and Dark Ace have Type I in Storm Hawks, to the point where Cyclonis laughs off one of Dark Ace's failures, and he seems willing to sacrifice his life to save hers.
 * Christy and Dark Heart in Care Bears Movie II: A New Generation, due to a Deal with the Devil,.
 * Chris Maclean and Chef Hatchet from the Total Drama series: Type II.
 * Chris Maclean and Chef Hatchet from the Total Drama series: Type II.