Spider-Man’s rogues gallery is a veritable who’s-who of monsters and misanthropes. Over the course of his decades-long career, Peter Parker has faced some of the most unhinged homicidal menaces New York City (and the world at large) has to offer. It’s not surprising, then, that some of Spider-Man’s villains have taken things entirely too far in their efforts to add more chaos to this cruel and indifferent world.
The enemies Spider-Man has fought have done some really messed up things to him that mark them as undeniably evil, but even then there’s a limit. There have been times over Spidey’s career where the reader has been forced to witness acts that can only be called demented or holy-balls-can-you-believe-that-guy-just-stole-Peter-Parker’s-body and became the Superior Spider-Man?
While other heroes have it hard, the worst things that Spider-Man villains have ever done would make Wolverine run back to Canada.
Norman Osborn Seduces Spider-Man’s Girlfriend, Gets Her Pregnant
In Amazing Spider-Man #509-514, a handwritten note sends Peter Parker down one of the darkest roads he has ever gone down. Parker discovers that not only did Norman Osborn kill Gwen Stacy, he also seduced and impregnated her beforehand (and she was pretty into it). Ugh.
Their children were born overseas in secret. Norman Osborn saw to their support, made sure they were educated and trained, and told them that Peter Parker was their father. Oh, also due to their Gobliny heritage, they aged super quickly. Because comics. The twins were told that Parker had abandoned them, killed their mother, and left them to die. Finally, Norman Osborn sent the children to destroy Peter Parker and all of his loved ones. So, the upshot is that Peter had to fight the children of his one true love and his greatest enemy, all the while dealing with the fact that Gwen Stacy cheated on him. It was a… rough time for the wall-crawler.
Sin-Eater Murders A Priest During A Confession
NYPD Captain and popular Spider-Man ally Jean DeWolff is dead, shot at close range with a double-barreled shotgun in her own apartment. It’s a cheery way to start a story. Anyway, Spider-Man, Daredevil, and the entirety of the NYPD go on the hunt for her killer. While they search, the Sin-Eater continues his rampage across the city, eliminating anyone he deems guilty of sin.
Perhaps the most brutal of the Sin-Eater’s acts is the murder of Reverend Bernard Finn, a religious figure known for speaking in support of prison reform. Sin-Eater enters Rev. Finn’s confessional, and talks to the reverend about his self-doubt and flagging resolve.
Oblivious, Reverend Finn encourages him to remain true to his convictions, and to himself. In hindsight, this was probably a bad move. Sin-Eater thanks the Reverend for telling him what he needed to hear, then shoots him point blank with a shotgun, blasting him right out of the confessional in Spectacular Spider-Man #108.
Morlun Eats Spider-Man’s Eye In Front Of Him
Peter Parker is dying. A radioactivity-based infection is eating him from the inside, and despite the thousands of times Spider-Man has risked his life, this looks like his final battle. Reed Richards, Bruce Banner, T’Challa, and even Doctor Strange are all unable to save his irradiated life.
When Peter Parker is at his weakest, the villain Morlun attacks Spider-Man. The web-slinger is unable to mount a defense that even remotely slows his vampiric opponent’s onslaught. Peter puts everything he has left into a vicious flurry of blows, and it appears that he’s beaten Morlun into submission. Then Morlun goes ahead and rips out Peter’s left eye, devouring it in front of him before beating Spidey close to death in Amazing Spider-Man #526.
The Green Goblin Brutally Breaks Spider-Man’s Spirit
Norman Osborn, AKA Green Goblin, isn’t exactly what you’d call “well-adjusted.” Or, you know, “merciful.” So when Osborn kidnaps Spider-Man and tortures him (both psychologically and physically) with the intention of making him his heir, it’s both horrifying and totally in character. Classic father-and-son stuff.
Eventually, Peter musters the strength to fight back and reject Norman Osborn’s twisted gift of darkness. He beats the crap out of the Green Goblin, but it doesn’t matter. Osborn knows that even though Spider-Man is stronger and smarter than he is, the Goblin has broken him. Osborn’s work is done, and in Spectacular Spider-Man #25 he leaves a weeping, unmasked Spider-Man behind him. For a while after that, Spider-Man is kind of a huge bummer to hang out with.
Carnage Penetrates The Mind Of A Therapist
Doctor Kafka of Ravencroft Sanitarium spent a lot of time and effort trying to help the nightmarish killing machine Cletus Kasady, AKA Carnage. Unable to help him, Kafka calls in Matthew Kurtz from the Pentagon for assistance in rehabilitating the murderous psychopath.
Kurtz uses a sonic gun to control the alien symbiote in Kasady’s blood, also utilizing massive doses of psychotropic drugs to control Kasady himself. Kurtz peels back the layers of Kasady’s mind, cutting to the heart of Carnage’s psychopathy: it’s not just that Kasady loves to kill, he considers himself an artist.
When the drugs unexpectedly wear off early, Kasady attacks Matthew Kurtz with unearthly speed. Carnage drives a corkscrew spike into Kurtz’s mind and pumps his own twisted view of life and existence directly into Matthew Kurtz’s mind. The visions of unrelenting violence change Kurtz for the rest of his very short life as Carnage watches, contented and amused.
The Green Goblin Damages Flash Thompson’s Brain
Green Goblin loves messing with Peter Parker. It’s unstoppable, like the tides or new seasons of The Bachelor. As is often the case, Osborn wants Parker to join him as heir to the Osborn Empire. Barring that, he wants Parker to kill him or die knowing that Osborn will then kill everyone Parker has ever loved. Osborn doesn’t really do grey areas.
To motivate the web-slinger, the Green Goblin forces a full bottle of whiskey down the throat of recovering alcoholic Flash Thompson, and then puts him behind the wheel of a speeding truck. A real classy move. The truck is pointed directly at Peter Parker’s unoccupied public school classroom (he’s a teacher in this story), and the ensuing crash leaves Thompson with permanent brain damage in Peter Parker, Spider-Man #45.
The really messed up part? This was all tangential to the Goblin’s main plan. He just wanted to make Spider-Man mad, and he ruined a man’s life to do so.
Doctor Octopus Takes Over Peter’s Body, Becoming Spider-Man
Otto Octavius, AKA Doctor Octopus, was always prone to biting off more than he could chew. Thus, it’s no surprise when he’s pushed to the point of death, the victim of years of radiation and the stress of those monstrous tentacles on Otto’s all too human body. Ever the planner, however, Doctor Octopus has a contingency in place. Peter Parker is forced on two separate occasions to link his mind to Doctor Octopus’s “octobot” technology, and in doing so the process he gives Octavius everything he needs to complete his nefarious scheme.
Octavius steals Peter Parker’s body; his strength, his powers, his memories, everything. At the same time, he forces Peter Parker’s frenzied consciousness in to his own frail, dying body. You know, so things are fair and balanced. In Amazing Spider-Man #698, Octavius takes control of Peter’s life, and it’s exactly as terrifying and degrading as you’d imagine. He does, however, refrain from trying to seduce Mary Jane Watson while in Peter’s body, something that the “hero” Wolverine did in a similar situation.
Kingpin Gets Aunt May Shot
Wilson Fisk discovers Spider-Man’s secret identity, and as the Kingpin rots in prison, he orchestrates the murder of Peter Parker. After the events of the first Civil War series, Peter Parker is a wanted fugitive and his Aunt May and Mary Jane have been forced into hiding.
Wilson Fisk has snipers on both of them ,with orders to fire on his command at the end of Amazing Spider-Man #538. When Peter Parker meets up with them at a nondescript motel they believed was secure, Fisk gives the go-ahead to take the shot on Parker. He also wants Mary Jane and Aunt May murdered as well, because he’s not one for loose ends.
Parker dodges the shot easily, saving his wife in the process. Aunt May, however, is hit by the sniper’s bullet and critically injured. Basically, he shot an old woman just to prove a point. Later, Peter Parker beats the snot out of Fisk during a prison riot, threatening to kill him if he doesn’t back off. It takes a pretty traumatic act to push the Friendly Neighborhood Spider-Man to that point.
The Hobgoblin Brainwashes, Frames, And Murders Ned Leeds
The late Ned Leeds’s reputation as a decent man is one that lives on to this day in the story of Spider-Man. When Parker realizes Betty Brant could never accept his life a superhero and ends their relationship, it’s Ned who was there to pick up the pieces.
So, it’s a pretty big deal when the Hobgoblin, one of Spider-Man’s most formidable enemies, is revealed to be Ned Leeds. The evidence appears incontrovertible. Ned is the victim of professionally executed hit, and when he’s murdered he’s actually wearing the Hobgoblin costume.
Later, it’s revealed that Ned had actually been brainwashed into believing he was the supervillain, even as he was garroted to death in Amazing Spider-Man #287. Leeds’s framing and murder was the result of Roderick Kingsley’s (the original Hobgoblin) scheming. Kingsley used his immense power to make himself rich, leaving the brainwashed Leeds to take the fall. For years, though, Spider-Man believed his closest friend was actually one of his greatest enemies.
Kraven Buries Spider-Man Alive, Steals His Identity
Kraven the Hunter is one of the only villains to truly defeat Spider-Man in a lasting and impactful way. Kraven shoots Spidey in the face and buries him in the ground. This is twisted enough, since he knows Spidey isn’t dead, but then he actually replaces Peter Parker as Spider-Man in Amazing Spider-Man #31. He begins dispensing his own brutal form of justice to the villains of New York, tarnishing Spider-Man’s reputation.
When a traumatized and exhausted Peter Parker digs his way out of the ground, he confronts the creepily docile and affectionate Kraven. Instead of fighting him, Sergei Kravinoff kills himself, landing in a coffin with a picture of his family by his side. He knows Parker will never be able to rob him of his victory.
Carnage Drives His Therapist And A Security Guard To The Brink Of Madness
In Carnage: It’s a Wonderful Life (by horror comics legend David Quinn), Ravenscroft Sanitarium is closing and the odds are that all of the deranged, super-powered inmates will be released by lawyers who don’t truly understand the threat they pose. Chief among them is Kletus Kasady, the violently insane Carnage.
After the events of Carnage: Mindbomb, it’s clear Kasady is a hopeless case. Doctor Kafka (Kasady’s therapist) and John Jameson (head of security for Ravenscroft) only have one option left: trying to shut down Kletus Kasady’s brain from the inside.
Carnage, horrifyingly, is thrilled at the idea. That probably should have been a clue that it was a terrible plan. The trip through Kasady’s mind is a nightmare come to life, one that Jameson is particularly susceptible to. In the end, Kasady takes the two of them to the heart of his madness, transforming them as they run through the accumulated pain of his existence. While they eventually escape, both of them are forever changed, and the damage to their psyches may be irreparable.
Doctor Octopus Tries To Marry Aunt May
An “in the background” story arc that spanned about seventeen issues, this debacle ranks up there with some of the most debased, demented acts any of Spider-Man’s enemies have ever attempted. To begin, it is revealed over the course of several primary story lines that May Parker has inherited a Canadian island (so exotic).
In fact, not only has she inherited a Canadian island, she’s inherited a Canadian island that sits on top of wealth of uranium with a nifty nuclear reactor to top it off. That’s right, Aunt May is basically a nuclear power. Since a nuclear reactor and a sh*tload of uranium can be infinitely handy for a villainous megalomaniac, Otto Octavius devises a brilliant scheme to get his many hands (and claws) on it.
He romances the old-as-dirt version of Aunt May, then plans to marry her. This would make him the owner of half of the island – uranium, reactor, and all. Afterwards, of course, he intends to murder her so he’d be the sole owner. Whether or not he intends to consummate the marriage beforehand is up for debate.
Luckily, Spider-Man is able to interrupt the nuptials by kicking the crap out of Doc Ock. Later, Octavius and third-tier Spider-Man villain Hammerhead brawl at the aforementioned nuclear reactor and inadvertently trigger a meltdown.
Mac Gargan Eats A Whole Bunch Of Gods
Following the Secret Invasion storyline, Norman Osborn takes a collection of antagonists and former villains and gives them the names and likenesses of the Avengers. This group of Dark Avengers is tasked with rescuing Doctor Doom from the clutches of Morgana Le Fay, who’s a bit ticked off with the Latverian dictator for having betrayed her trust and stolen her secrets.
She’s about to plunge a dagger into the heart of Victor Von Doom, ending his menace once and for all, when Osborn’s Dark Avengers intercede. In the ensuing battle, Mac Gargan (fused with the Venom symbiote and bearing the name Spider-Man) suddenly finds himself under the control of Morgana Le Fay after Sentry fails to kill her. For all their new power, the Dark Avengers are simply no match for Le Fay. She drives the point home by having Gargan devour the Olympian Ares whole.
Later, during the Siege of Asgard storyline, Gargan remembers his predilection for divine flesh and kicks bricks halfway through a major battle and just kind of hangs out eating Asgardians.