From the top: Stupidly overpriced first issue; Title (if you can read it) includes "Blood"; Publisher (again, if you can read it) you've never heard of; Improbable blade; Torn cape; Wolverine knock-off mask that frames face; Gritted teeth; Improbable anatomy; Improbable gun; Lots of pouches; Artist's signature on rubble.
"1993 was the year Superman died and Venom got his own series. Just keep that in mind."
The general characterization of Kurei from Flame of Recca after the Tournament Arc. Despite separating himself and his loyal followers from the Uruha, and pursuing the same quarry as Recca and his allies, his vicious and ruthless nature remains unchanged, even until the end of the series.
Killy from Blame!is this trope - minus the "hip" clothing and ridiculous muscle mass. The series was even created in the mid-90's.
In Tiger & Bunny, the inhabitants of Sternbild City are introduced to the concept of the Nineties Anti-Hero with Lunatic, a menacing vigilante who unhesitatingly kills criminals, racks up the property damage like nobody's business, and mocks the established superheroes for their idealistic 'weakness'. Given what end of the Sliding Scale of Idealism Versus Cynicism the show occupies, he serves as both a villain and a Knight of Cerebus during his introduction. Though later episodes in the series put him in a more sympathetic light.
Black★Rock Shooter: The eponymous heroine has the idiosyncratic name spelling, skimpy clothing, Badass Longcoat, fights without uttering a word with her humongous, morphing cannon and black katana and fights to kill. Add the ability to shrug off lethal wounds without blinking and a blue flame around her left eye and she's only missing a thing: the Most Common Superpower.
Comic Books
Cable◊, of the New Mutants, X-Force, and the X-Men was a major Trope Codifier. Tragic and mysterious past? Check. BFGs coming out the ass? Check. A "badass" look that used to be reserved for villains? Check. His first appearance was even in 1990, Over time, though, he's been developed into a more complex character, somewhere between Messianic Archetype and A God Am I.
Image Comics specialized in these for as long as the fad lasted:
Spawn, quite possibly the most popular Nineties Anti-Hero. Edgy one-word name, grim-n-gritty backstory (an assassinated mercenary damned to Hell and sent back as a soldier of Satan), killing bad guys who were slightly worse than him, and written and drawn by Todd McFarlane.
Spawn is a very interesting example, as a lot of effort is put into humanizing him and he comes off as a far better character than the average Nineties Anti-Hero. But then, being around for a while tends to do that.
The first issue of Spawn also had a little parody of the tropes common appearance. Entertainment TV Talking Heads commenting that while the spikes and chains are "totally gauche", trying to bring back capes is a bad idea.
The Darkness and Witchblade both exemplified this trope. The former is a former mafia hitman who becomes a living vessel of the world's dark energies, complete with an army of flippant, happy-go-lucky demons who delight in every opportunity to torture someone; the second is a pornolicious detective with powers both lethal and which rip her clothes off whenever she uses them.
During the early '90s, Bloodlines, possibly the most loathed Crisis Crossover to hit The DCU, produced a glut of Nineties Anti Heroes, few of whom lasted more than a couple years, including Gunfire, Mongrel, Razorsharp, etc., etc. Probably the only one to be remembered fondly is Hitman, a, well, super-powered hitman, who alternated between being a paragon of the trope and a clever send-up.
Hitman also blatantly parodies this trope when Tommy encounters Nightfist, a Batman ripoff who takes out drug dealers with a pair of giant metal fists (which he wears over his normal fists) and then steals their drugs.
Around 1994, Guy Gardner, a roughnecked, "macho" member of the Green Lantern Corps, was reinvented as "Warrior," with ridiculously huge muscles, tattoos all over his body, and the ability to form his arms into any kind of weapon he could think of, mainly gargantuan guns. Rumor has it that the reinvention was the result of writer Beau Smith writing the pitch as a joke and accidentally having it approved. He eventually reverted to his old (but still roughnecked) Green Lantern persona after the fad played itself out.
Kingdom Come, by Mark Waid and Alex Ross, was in part a savage denouncement of Nineties Anti Heroes, and was one of the things that caused the changeover from the Dark Age to the Modern Age. One of the themes of the comic was the classic generation of superheroes fighting the violent "modern" heroes. Of course, the "classic" heroes shared some of the blame as well; many became just-as-violent Knight Templars attempting to deal with it. The "face" of the anti-heroes, Magog, is practically every Dark Age stereotype rolled into one cybernetic, sacrilegious package (though Waid and Ross admitted a certain fondness for him due to how over-the-top he was). In a brilliant twist of idealism, Magog realizes how screwed up he is, turns himself in, renounces violence, and is one of the people left alive at the end; in the prose novelization of the story, he becomes the Dean of Students at Paradise Island!
Magog himself was able to pull a Canon Immigrant, and was introduced in the Main DCU in a JSA storyline. In 2009 he got his own solo series, which is something of an Affectionate Parody of the old school Nineties Anti-Hero. His Rogues Gallery includes an insane homeless man with mind control powers and a silver haired woman who talks like a 1980s valley girl.
Marshal Law is an Anti-Hero who specializes in hunting heroes, though as he always says, "I haven't found any yet."
Likewise, in The DCU, Jason Todd (Batman's second Robin) has been a Nineties Anti Hero type ever since he came back from the dead. Amusingly, he was absent for the entire decade.
The Authority represent an entire Justice League of Nineties Anti-Heroes. They are, however, unusually idealistic for their kind, as part of their remit is to "make the world a better place". Their methods, however, seem to involve copious amounts of ultra-graphic violence (no Thou Shalt Not Kill for them), ruthless cynicism towards their enemies, and disdain for opposing points of view — they once overthrew the government of the United States. Their idealism, in many cases, only makes them worse than the standard cynical nineties anti-hero. This editor was once amused, however, to see them described as 'hippies'.
It should be noted that most of the above characteristics are often attributable to the post-Jenny Sparks era, as under her leadership the team tried as much as possible to exercise some discretion when it came to collateral damage (even helping in the clean-up, afterwards). They were still all for balls-out killing of hostiles, though.
They're presented more like Well Intentioned Extremists, which as said, makes them both more dangerous and more interesting than your average 90s antihero.
Or, they're Golden Age heroes played straight in a modern world. None of the Golden Age heroes had any problems with killing, most criminals being disposed of by the dozens. It wasn't until the Silver Age all the talk about "Thou Shalt Not Kill" came up.
Cyclops, of the X-Men, had his personality largely unchanged, but despite having been nicknamed "Slim" his whole life suddenly developed a chest that pro wrestlers would find intimidating.
His personality has changed later though. During Grant Morrison's New X-Men and especially after he became pretty much Nineties Anti-Hero despite the fact that it started in 2003.
The second-tier Marvel superheroes Darkhawk and Sleepwalker, both of whom had their heyday in the early 1990s, are arguably subversions of this trope. While they have strange and bizarre appearances, neither one was especially dark in their tone, at least compared to titles like Spawn, or the other characters that exemplify the Nineties Anti Hero. Darkhawk was about a kid who followed in his policeman father's footsteps by fighting crime with the mysterious alien armor he had obtained, while simultaneously keeping his Nuclear Family from falling apart. Sleepwalker was about an alien from another dimension that became trapped in a human's mind and manifested to fight crime while he was asleep, carrying on the similar role he had carried in his home world. There were, both in the letter columns of the old Sleepwalker comics and more recent web postings, positive responses from fans who liked the fact that Sleepwalker wasn't a violent antihero.
Darkhawk is actually an interesting case of this, as he at one point finds a journal of his father's, the last entry stopping with him and his partner preparing to go in pursuit of a hit-and-run driver before seeking medical attention for his victim. Chris refers back to this several times to remind himself to take a harder edge, before discovering the journal had a stuck page, in which his father hesitates, calls an ambulance, and makes sure the old woman who was hit survives.
Penance in the Marvel Universe, originally the happy-go-lucky character Speedball, is a strange version of this. After believing himself responsible for the death of 612 people in Civil War, he designs a costume in dark colors designed to give himself constant pain with 612 spikes. This was intended seriously, but having happened long after the 1990s, is treated like a parody in most of his appearances outside Thunderbolts.
And, very tellingly, is sent to see a psychologist!
The late eighties and early nineties had the Teen Titans sister team, the "Team Titans," who were this to the point that one of them took to calling himself Deathwing.
Wolverine went from being a complicated, interesting character in the 80's to "stabby stabby stabby!" in the 90's. It took the recent "Enemy of the State" and "Wolverine: Origin" stories to restore his former glory.
Bloodshot: Mobster Angelo Mortalli was framed by the Carboni crime family, forcing him to become a witness for the state. While under Federal protection, Mortalli was betrayed by his protectors and sold to Hideyoshi Iwatsu to become a test subject for Project Rising Spirit.
H.A.R.D. Corps: A group of Vietnam veterans who where revived from comas by a corporation who fits them with brain implants that give them psionic powers, and explodes if they're killed, or caught. One of them dies in every other issue, so they're always being replaced.
The recent (and ongoing) "Winter Soldier" mega-arc by Ed Brubaker in Captain America subverts a lot of these tropes. When Cap's sidekick Bucky turned out to be Not Quite Dead after all, he was revived as a brainwashed assassin with a cyborg arm; it could have been really stupid, but it wasn't. Then, when Bucky took over as Captain America, he seemed poised to be a grim and gritty alternative to the more traditional model, with much made of him carrying a gun — however, Bucky almost never uses the gun, and in fact tries overcome his past and be a more traditional superhero.
Spider-Girl has AprilParker, that is simply a jerk version of main protagonist with powers of Venom. She fits this trope perfectly, right to the point that woman she once saved from bandits run away, because she was more violent that they. Oh, and she killed Tombstone too.
Venom. First there was the "black suit" Spider-man, basically a Nineties Anti-Hero before his time, caused by an alien symbiote bonding to him. He later removes the symbiote, and it bonds to another man, becoming Venom, basically an Evil Spider-man. That would have all been well and good, except Venom proved to be something of an Ensemble Darkhorse, and entered his peak of popularity during the peak of the Nineties Anti-Hero's popularity, and thus Venom was given his own Comic and re-worked into one. Then they have Venom's Symbiot give birth to a second one, which bonded with a serial killer to become Carnage, an evil(er) Venom. This opened the floodgates. Venom's symbiote gave birth to 4 more Symbiotes, but these fused into a single one which bonded with a police officer to become another Nineties Anti-Hero Hybrid, meanwhile Carnage's Symbiote gives birth to yet another symbiote which bonded with another police officer to become yet another Nineties Anti-Hero called Toxin.
Morbius. Edgy leather gimp suit, magical demonic powers, slaughtering bad guys by the dozen, less moping and more badass-itude and even more exaggerated 90's villains to fight with... Only aversion might be that the 90's comic made him more generic handsome.
Shadowhawk was a Image Comics title about a successful, scrupulously honest African-American attorney who refused to fix a case for an organized crime outfit and, in revenge, was kidnapped by them and dumped after being given an injection of the AIDS virus... which prompted him, in a fit of rage and desire to try and make some sense out of the world, to don exoskeletal armor and start brutalizing thugs as a vaguely Batmanish vigilante. The suits got more and more elaborate as the disease took its toll, to help compensate for his weakness, but he ended up dying of the disease anyway.
Apparently even series creator Jim Valentino "hated" the character, and killed him off purely out of spite. Why he even bothered with the whole affair in the first place is anyone's guess.
That may be why the second Shadowhawk ended up so... different.
In 1994, DC turned Doctor Fate into an Anti-Hero named Fate who was a grave robber and had melted Dr. Fate's helmet into a knife.
Even Superman and Batman had them! For Superman, it was the Eradicator, one of the four replacement Supermen who appeared after he died. For Batman, it was Jean-Paul Valley, the man formerly (at the time), known as Azrael, who replaced him after Bane broke his back. Nightwing chewed Bruce out over it and Bruce himself admits it was one of his worse mistakes.
Johnny the Homicidal Maniac parodied both the male and female versions of this trope in one of its "Meanwhile" stories.
Film
Mr. Furious in the movie Mystery Men is a parody and subversion of these kinds of characters; he would very much like to be one, and tries his hardest to come up with a back story fitting this mould (with most of his proposed names being some combination of 'Phoenix', 'Dark', 'Dirk' and 'Steel'), but is in fact ultimately a rather shy, gentle and meek man called Roy. In fact, the realization that he's not one of these types is enough to prompt a moment of Heroic BSOD for him.
Literature
Parodied in The Man in the Ceiling by Jules Feiffer. Jimmy's friend Charley Beemer (who doesn't like capes) commissions him to draw his idea of a comic, which would feature a superhero named Bullethead, a weapon of death who drills through his enemies with his head, with lots of severed bodily parts to be drawn in detail.
Live Action TV
Iron Enforcer represented this type of "super hero" in the first season of Who Wants to Be a Superhero?. Unfortunately for him, Stan Lee is not fond of this archetype. So he made him a villain instead.
An episode of Dexter features a comic book character based on him (The Dark Defender) that is a perfect 90s Anti-Hero.
The "real" Dark Defender, upon seeing a pin-up of the character, has the most satisfied smile on his face for all of three seconds before he shakes it off as absurd not for any moral reasons(Dex is a Poetic Serial Killer and proud of it), but because, "Miami's too hot for all that leather"
An episode of Criminal Minds has a comic book artist create a character named "True Night" who seems to be one of these. It has plot significance because the ways Night kills the other characters in the comic reflect murders the artist is committing in real life. In fact, if one looks at the episode a certain way, it can be viewed as a brutal deconstruction of this trope and Dark Age comics in general.
Similar to the above, was a serial of Kamen Rider Double. The Cockroach Dopant runs a website where people list those that have wronged them for him to assassinate. While basically a glorified contract killer, he considers himself this trope, calls himself "Roachstar" and "the Dark Exterminator", and even has and draws his own manga in-universe.
The obscure 90s comedy series Bob, starring Bob Newhart, focused on a comic book creator of a Silver Age hero named "Mad-Dog", who was forced by his new employers in the 90s to reinvent his character into a hero of this fashion.
This was the direct result of having to compete with WCW, who hit on this concept with the New World Order, however the nWo were actually just popular villains, at least until the Wolfpac formed.
In some ways, it was more a reaction to the growing underground success of ECW, and fueled by a number of wrestlers who developed grittier gimmicks in ECW and later brought them to WWF (like Steve Austin, himself considered one of the core on-screen forces behind the change). The WWF's "Attitude" era was almost entirely based around the harsher, more adult aesthetic pioneered by ECW.
The concept may have been inspired by the underground success of ECW, but the need to change was a result of WCW's runaway success with the nWo angle.
The ongoing success of MMA (UFC in particular) in 2010 has seen a partial revival of this trope in WWE with the resurgence of the newly-turnedRandy Orton (especially when compared to his Hoganesque counterpart John Cena).
Video Games
Tombstone from Freedom Force vs The Third Reich, a series that is an homage to the high Silver Age of comic books, is a Nineties Anti-Hero. And he still fits into the game, because his overblown "dark and tormented" act makes him just as laughable as the rest of the cast.
Alchemiss: [sarcastically] So how did you spend your sabbatical, Tombstone? Performing in musical theater? Raising puppies?
Tombstone: animals wither in my presence.
Shadow the Hedgehog seems to be a played straight born-too-late Nineties Anti Hero, especially when he got his own game where he used guns and rode motorcycles.
Ironically, it was only after his Darker and Edgier game that he softened up. His angsting and amnesia were cleared up, and he was able to vent his rage on a malevolent alien race.
Duke Nukem. A sex obsessed, mirrorshade wearing action hero wannabe who hangs out in sleazy biker bars and strip clubs, with a Lantern Jaw of Justice and blond flattop haircut. He's armed to the teeth with BFGs (as it's a FPS and all), addicted to steroids (or whatever those pills are) and loves to spew one liners like "I've got balls of steel", "Some mutated son of a bitch is gonna pay!" and of course the immortal "It's time to kick ass and chew bubble gum. And I'm all out of gum." And his games were big in the early 90s. Duke is generally accepted as being a full parody of the 80s/90s action hero rather than actually being one. He's no exception to the fact that most parodies and extreme cases of this are deeply entrenched in Poe's Law though.
By the standards of JRPGs, Caim from Drakengard is a Nineties Anti-Hero, bordering on straight-edge villain protagonist if not for the happy side effect that the people he happens to be on a genocidal rampage against want to destroy the world.
Renegade!Shepard in the Mass Effect series: a ruthless and pragmatic person, willing to take the morally grey (or outright black) actions to get the job done. Basically, s/he is out to save the galaxy, but doesn't much care who or what s/he tramples to get there. Some of the Renegade choices available (particularly in the first game) can paint Ren!Shep as uncaring, incredibly xenophobic and a human supremacist with near sociopathic levels of disregard towards others.
Asshole!Warden in Dragon Age has a tendency to wander through Ferelden, kicking ass and taking names, while slaughtering whatever unconscious wounded soldiers or small children get in the way, condemning a significant number of elves, men, and dwarves to And I Must Scream fates for the sole purpose of getting cooler-looking allies during the final battle, and slaughtering the entire Denerim Circle of Magi for the sake of convenience.
The Legacy Of Kain series gives us an 2 interesting examples. While Kain is more or less a straight example character wise, Raziel is a much more heroic/noble character, however, his character design positivly drips of it. The reason for this is because the game Dev team outsourced the concept art to Top Cow (a comic studio that broke off from Image, responsible for such works as The Darkness and Witchblade). The reason for this is because of complex corporate politics behind the creation of Soul Reaver, which was being made at the same time as Eidos was having Top Cow publish the Tomb Raider comic.
Ballistic, Fusillade, and Ablaze are all good examples as well.
Western Animation
Spoofed in an episode of The Fairly Odd Parents, where Timmy called upon the help of several different versions of the Crimson Chin to defeat an escaped supervillain, including a bandoleer-wearing, gun-toting "edgy" version of the Chin from the eighties. He was apparently the only version that ever got away with profanity, but was canceled because of it anyway.
Spoofed in The Tick with Big Shot, a Punisheresque character who shoots up inanimate objects while tears run down his face. After running out of bullets, he says "Why didn't you love me, Mom?" and collapses, sobbing, on Arthur.
He's someone so obviously messed-up that the Tick tells him to 'seek professional help'— the Tick!
He actually does seek professional help between episodes. When next seen in "The Tick vs. The Tick," he's relatively well-adjusted and tries to convince the Tick and Barry to discuss their problems rationally.
With emphasis on 'relatively' well adjusted. He starts foaming at the mouth when he mentions how he used to solve all his problems with... violence, and gives a rather, um, passionate outcry for Barry to "put it in the happy box!". In his final appearance in the show on "The Tick vs. Neil and Dot's Wedding", Big Shot goes on a shooting spree... With a camera, having channelled his enthusiasm for firearms into flash photography.
When the Powerpuff Girls briefly decide to split up as separate superheroines, with Blossom taking on a Wonder Woman-ish persona and Bubbles dressing up as a cute bunny girl, the sullen and quick-tempered Buttercup reinvents herself as "Mange", a brooding, shadowy character with glowing green eyes who only emerges at night. Unfortunately for Townsville, this means she has to wait until nightfall to stop a monster attack in the middle of the day: she spends the hours beforehand just brooding awkwardly in the living room.
While not exactly a superhero, Matrix in ReBoot is pretty much this trope to a T, as a foil to Bob's idealistic Silver Age-ish personality.
Matrix also serves as a partial deconstruction of this type of hero. The events that made him this way left him an emotional wreck and he has difficulty adjusting to peace.
While developed after the 1990s, Brock Sampson is a semi-affectionate parody of this trope
Darkwing Duck became one of these in an alternate future where Gosalyn disappeared (because she had been sucked through time into that alternate future).
He might've been this earlier on, but by the time Gosalyn ran into him he had long ago crossed the line and was solidly in the Knight Templar category.
