Psycho Sidekick

""Mouse was the truest friend I ever had. And if there is such a thing as true evil he was that too.""

- Walter Mosley, A Red Death

A trope common in private eye novels since the 1980s, and occasionally found in other genres. Sometimes, your morally spotless hero has a buddy who's a lot less morally spotless. Often, they've been friends for so long that a bit of moral divergence hasn't spoiled it. On the more moral end of the spectrum, the friend's a Hitman With a Heart or Loveable Rogue. In Darker and Edgier cases, the friend is actually a Punch Clock Villain, Noble Demon or even a Psycho for Hire, but they deliberately avoid any situation that might actually pit them against one another because it would be just too painful. Of course, the friend could be just a little bit more violent or ruthless than the hero.

When this comes in useful is when the hero has to do something that they don't feel they can do, most often killing somebody who is certain to do horrible things to them or their loved ones or innocent bystanders, but who is too sneaky or too unsuited to combat for them to be conveniently able to kill them in self-defence or some kind of fair fight. At this point the Psycho Sidekick can step in and shoot the helpless guy in the face while the hero feels some slight angst but is grateful that they didn't have to do it.

Contrasted to the case of the Poisonous Friend, in which the main character is genuinely unaware of what the friend is doing. In this case, the main character is perfectly aware of the type of person their friend is and what they do for them. Naturally, this does come across as a bit hypocritical. Sometimes the hypocrisy is ignored by the story, but more often it's lampshaded. It's sometimes explicitly or implicitly argued that the ruthless act isn't so much wrong per se, as something that would brutalise the hero to the point that they'd lose their compassion or ability to empathise with others or ability to act as a moral exemplar to others.

Can be seen as something of an inversion of The Watson, as in the original case of the Sherlock Holmes stories, and in many others, part of the Watson's role is to smooth things over socially and upbraid the main character mildly when he becomes too much of a Jerkass, Sociopathic Hero or Insufferable Genius.

Note that if they're actually psycho, the arrangement usually won't work (but see the Walter Mosley novels discussed below).

Can also be defined cynically as The Dragon, but working for a Designated Hero. Compare Big Bad Friend for when the friend keeps their and evil tendencies and plot under wraps. One of these in an ensemble is the Token Evil Teammate.

Anime And Manga

 * Mirai Nikki: At least in the beginning while Yukki still has his moral compass in the fully upright and locked position, Yuno Gasai is what happens when you mix this trope with Yandere and shake rapidly.
 * Virid the Mad Prince from There Beyond the Beyond, staying true to his name.

Comic Books
"Damian/Robin: Now whose neck do I break first?"
 * The League of Extraordinary Gentlemen Victorian-era team actually consists of 60% Psycho Sidekicks and 40% relatively moral people. When a vampire attack-survivor music teacher and an opium-addicted hunter are the normal guys, have fear. And now Orlando is tending that way in Century.
 * Wolverine sometimes plays this role in X-Men, in issues where the other characters are being depicted as relatively pacifistic.
 * Cassidy in Preacher, until we find out some of the things he did in his past...
 * A JLA/Hitman miniseries depicted Tommy Monaghan as a Psycho Sidekick for Superman, and explicitly stated the moral justification of the trope described above.
 * And Natt 'The Hat' to Tommy in the regular Hitman series. Natt does things like shoot the subdued prisoner (he was only going to be sent back) and kill the innocent staff of the mafia safehouse (Tommy said 'Kill everyone'). It becomes apparent over the course of the series that Natt only (mostly) follows Tommy's creed of 'kill only bad guys' because he values their friendship.
 * Captain America: Bucky Barnes is portrayed this way in current books, as a creative Retcon explaining his 'harmless' sidekick persona was actually a front for shady activities a public figure like Captain America couldn't be caught doing. He makes quite a darkly hilarious contrast to the older and unfailingly idealistic Cap.
 * Bruce Wayne's son Damian tries to become the psycho equivalent of Robin to Batman, to the point of trying to dispose of Tim Drake in his first appearance.


 * Jailbait and Headcase to Max Damage in Incorruptible. Jailbait was Max's sidekick/underage lover when he was a supervillain, and hasn't taken his Heel Face Turn and Jail Bait Wait well at all. The last straw was when he left her behind in an attempt to keep her safe. Since she's a bloodthirsty adrenaline junkie, that was the worst thing Max could do to her. Her successor Headcase is even worse -- the murder of her whole family unhinged her so badly that she's now a Death Seeker with Max as the only anchor she has in life.

Film

 * Let's see now. Is this a film about wiseguys? Is Joe Pesci doing his Hair Trigger Temper routine? Yup? Well, there you go. To list a few examples; Casino, Goodfellas.
 * Walter Sobchak from The Big Lebowski is The Dude's best friend and a walking Berserk Button.

Fanfiction

 * In the Good Omens fanfic The Sacred and The Profane, 'Zirah' (Aziriphale) is a chillingly ruthless Psycho Sidekick to 'Caphriel' (Crowley),.

Literature
""If you didn't want him dead, Easy -- why did you leave him with ME?""
 * Hawk in Robert B Parker's Spenser novels: the type specimen for the trope and one of the first to appear, resulting in a Fountain of Expies.
 * Mouse in Walter Mosley's Easy Rawlins novels. A particularly extreme example in that he's genuinely Ax Crazy. And brilliantly played by Don Cheadle in the 1995 film adaptation of Devil in a Blue Dress.

""And sometimes a fellow who does one job well can see where his job has to be done, even though a better man has overlooked it. Anyhow, Secretary, there always was one thing you and I could agree on -- lives are cheap.""
 * Clete Purcel in James Lee Burke's Dave Robicheaux novels, although Dave can get a bit more morally ambiguous than is usual in such cases.
 * Bob the Skull in Jim Butcher's The Dresden Files series. He's a spirit of intellect, and thus doesn't wholly understand the "morality" thing. Kincaid stands well within Psycho for Hire in most cases, but acts as the Psycho Sidekick to the Archive.
 * Inverted in the case of Harry and Michael. While Harry is heroic, he is more likely to do morally dubious things than Michael, who dislikes people swearing.
 * Inverted a lot by Harry. He plays Psycho Sidekick to Karrin Murphy's advocacy of the law, and the White Council see him as useful psychotic that'll need to be shot sooner or later.
 * And on top of all of these you have . Being the Psycho Sidekick to the White Council is part of his job description.
 * Joe Pike in Robert Crais' The Monkey's Raincoat and the other Elvis Cole books. He actually has a moral code but is a lot more comfortable with violence than Elvis. He also has a few books centered around him.
 * Mick Ballou in Lawrence Block's Matt Scudder novels.
 * Hoppy Uniatz in Leslie Charteris's The Saint novels.
 * The Saint himself is actually worse than Hoppy. He has been known to coolly murder unarmed men, and on one (somewhat justified) occasion burned a group of criminals alive.
 * Stephanie Plum series by Janet Evanovitch: Ranger, although Ranger's a bit more cerebral than most examples, and significantly less psycho than average.
 * The Alloy of Law has Wax, an upstanding heroic member of society, working with Wayne, a partially-reformed thief whose definition of being 'reformed' tends to mean that instead of just stealing things he leaves something in their place.
 * Subverted in Carol O'Connell's Mallory novels, which are about a sociopathic primary character who would usually be someone else's Psycho Sidekick surrounded by sidekicks who keep her from going completely evil.
 * The Taltos books have been acknowledged as inspired by the Spenser series, but seem to turn this on its head. Vlad Taltos, the protagonist, is the Psycho Sidekick in relation to his friends who are fantasy elf nobility, but it's less that he is more bloodthirsty than that he is less bound by social conventions. This is played rather straight in Orca though as a Lawful Good police officer, who normally disdains assassins, has Vlad kill her partner who was a Corrupt Cop and a murderer.
 * In Lois McMaster Bujold's Vorkosigan Saga, Sergeant Bothari has elements of this, though Aral Vorkosigan is more active than most in acting as his Morality Chain and eventually gets him some much-needed medical intervention.
 * Major Joachim Steuben in David Drake's ~Hammer's Slammers~ series is in love with Colonel Hammer -- and there's nothing so awful he wouldn't do it if he feels it'd benefit the colonel.


 * Lee in Gordon R Dickson's Dorsai!. Due to an uncorrectable medical condition, he's unable to tell right from wrong and is socially dysfunctional. He knows this, and seeks a cause to keep him functioning. He'll do anything for that cause. Luckily, he found Donal, who keeps Lee from doing anything nasty. Also notable that Lee likely inspired Joachim Steuben, as David Drake is a fan of the novel.
 * Edward in the Anita Blake series (although it's not like Anita's such a saint).
 * Bubba Rugowski in Dennis Lehane's Kenzie and Gennaro Series.
 * Myron Bolitar series by Harlan Coben: Windsor Horne Lockwood III, or, Win.
 * In Animorphs Rachel is this to the rest of the team, although they're not exactly white hats themselves. Reached its peak in the final two books when Jake sent her to.
 * Eventually, Rachel herself lampshades how she was made into this--the other characters kept needing someone to do bad things for the greater good, and it became easier and easier for her to be that someone. The entire team functions to enable and justify her actions.
 * Willikins to Sam Vimes in Terry Pratchett's Snuff.

Live Action TV
"Sarah: What did you do?!
 * Doctor Who: Leela (and K-9, a bit). While the Doctor sometimes criticises her violence ineffectually, he doesn't often intervene to stop it when it's useful. Subverted with Ace, in that a vague description of the dynamic between them would make Ace seem like a Psycho Sidekick, but the Seventh Doctor is much more ruthless than she is in a less personally violent way.
 * Avon in Blakes Seven, with interesting consequences when he ended up as the central character. Unusually, Avon continues to act like a Psycho Sidekick -- but having authority this is a disaster for himself and everyone around him. It's aspects like this which make it feel like a show shot on the deck of a burning ship.
 * Gene Hunt (and sometimes Ray) in Life On Mars and Ashes to Ashes.
 * Both Derek and Cameron in The Sarah Connor Chronicles move around on the spectrum between this and Poisonous Friend in relation to the more moral Sarah and John. This occurs as early as the second episode, when Sarah holds

Cameron: What you couldn't."

"Derek: John Connor said to let you go. (pulls out pistol) I'm not John Connor."
 * Derek does it even more often, whereas Cameron can usually be persuaded not to kill people if John or Sarah are near. And aside from  all the people he kills were really close to him, namely

""I'll take the beating, because that's all you two amateurs are cleared to do. Then one night soon, I'm gonna break into your houses and kill each of you in your sleep. I'll probably start with you, Alfredo. That way Stephen here can have a few extra days with Marla and the girls. It's only fair.""
 * Guerrero in Human Target. A short middle-aged man wearing round Harry Potter glasses, in the show's premiere he says the following (in a completely low-key tone of voice) to a couple of Mooks who are trying to intimidate him:


 * Likely also a retired Psycho for Hire and a Pint Sized Powerhouse. Played by Jackie Earle Haley, better known as Rorschach from the Watchmen film.
 * Guerrero doesn't like to be interrupted.
 * Buffy the Vampire Slayer: While Giles is sometimes the Poisonous Friend, the "Scoobies" are well aware of his Ripper persona. Spike is this for Dawn; at certain points in the series, she adores him despite knowing that he would be back out slaughtering innocents if not for his chip.

Video Games

 * Knights of the Old Republic: HK47 and Canderous Ordo, plus HK again, Mandalore and to some extent Atton Rand in the sequel.
 * Black Whirlwind in Jade Empire doesn't know of a problem that his axes won't solve.
 * Several classes in Star Warsthe Old Republic get one, most notably Khem Val in the Sith Inquisitor storyline.
 * Mass Effect: Wrex the Proud Warrior Race Guy.
 * Grunt from the second game in the series also qualifies, perhaps even more so than Wrex. As Grunt's mental condition is essentially that of an adolescent who has had only minimal interaction with other members of his race, he lacks the discipline and self-control that an older, more experienced Krogan, like Wrex, has.
 * Jack, by her own estimation, is a "murdering psycho bitch".
 * The latter half of everybody's favorite crime-solving dog and rabbit duo Sam and Max. Very much so.

Web Comics

 * Little Sappho, the sidekick from The Adventures of Gyno Star, can be extremely violent when angered, and is often willing to do morally questionable things that Gyno-Star would never consider doing.