Sinister Six

In the rogue’s gallery of Marvel comics, few villains are more feared than those who comprise The Sinister Six. This gang of baddies has wreaked havoc for over 50 years and has gone through many iterations. They are primarily focused on defeating Spider-Man, but they’ve come for many other heroes, and even for fellow villains!

Founded by Doctor Octopus, The Sinister Six originally included Vulture, Sandman, Mysterio, Kraven the Hunter, and Electro. Film fanatics will know all of these characters, with the exception of Kraven, from their appearances in Spider-Man movies, while comics fans are familiar with their often bizarre versions from many decades of print storytelling.

With such a long legacy behind them, each member of the Six has had their fair share of mischief and cemented themselves as among the best and most recognizable Marvel villains. But though you may think you know all there is about these fearsome foes, they’ve all had moments that took us by surprise. Let’s take a look at the untold truth of The Sinister Six.

Aunt May almost married Doctor Octopus

Amazing Spider-Man Issue 130

You read that correctly. The fearsome Doc Ock, Spider-Man’s tentacled arch-nemesis, once got sweet for Peter’s Aunt May and even intended to marry her. In "Amazing Spider-Man" #131, which was published way back in 1974, we find our hero swinging into Doctor Octopus’s mansion, only to find him mere minutes from exchanging vows with Aunt May. The marriage would have gone through, too, if a gang of goons led by Hammerhead — who was feuding with Doc at the time — hadn’t busted down the door at that exact second.

Turns out that Aunt May had inherited an island with the world’s most advanced nuclear power plant on it after the death of a relative, and Doc Ock hired her as a housekeeper in order to seduce her and get his hands on that sweet, sweet nuclear energy. Ultimately, both Ock and Hammerhead wind up dead when Hammerhead head-butts his fellow supervillain so hard that the nuclear plant explodes. Spider-Man flies Aunt May safely back to New York, leaving readers to question what in the hell just happened. The ’70s, it’s safe to say, were a wild time for comics.

The Vulture gave Aunt May’s fiance a heart attack

The Vulture in Spider-Man: Homecoming

Aunt May’s troubles in love didn’t stop with Doc Ock — her boyfriend was once killed by Vulture! Sweet, old Auntie was recovering from coronary bypass surgery in a local nursing home when she met Nathan Lubensky and quickly fell hard for him. But Nathan, too, had heart trouble, as Peter found out after saving him from a mugging outside a bank.

Nathan proved to have a selfless, heroic streak, and it cost him his life. When Vulture tried to kidnap Aunt May from a yacht party ("Amazing Spider-Man" #336), Nathan seized the villain. Vulture used his superpowered wings to wheel off into the sky with Nathan, dropping him from an incredible height. Spider-Man, thinking quickly, managed to catch his Aunt’s paramour, saving him from a gruesome end. But Nathan suffered a heart attack from the scare and died soon after.

Aunt May just can’t catch a break when it comes to love, can she?

Kraven once hosted a Steve Irwin-esque nature show

Kraven the Hunter and Spider-Man in Ultimate Spider-Man

The "Ultimate Spider-Man" is one of the webslinger’s most beloved series, which found writer Brian Michael Bendis updating Peter Parker and his world for the 21st century to the delight of readers everywhere. One of the most significant updates was placing Kraven the Hunter in the role of reality television host. Originally inspired by the famous short story "The Most Dangerous Game," Kraven was a Russian hunter introduced in 1964 by Stan Lee and Steve Ditko. Having hunted his share of big game, Kraven decided it would be more fulfilling to hunt Spider-Man.

The "Ultimate" series continued this theme, but in updating it for the aughts, Bendis decided it would make more sense for Kraven to be a nature TV star in the mold of Steve Irwin. This version of Kraven didn’t originally want to fight Spider-Man. He was much more used to crocodile hunting and other outback shenanigans. But with his ratings dipping, Kraven’s producers suggested a publicity stunt: hunting down Spider-Man live from the streets of New York City. Reluctantly, Kraven accepted … and proceeded to humiliate himself for an audience of millions when Spidey took him out with a single punch.

Mysterio tricked Wolverine into killing all the X-Men

Mysterio creating mayhem

"Old Man Logan" takes place in a world where there are no more X-Men. But few know the reason provided by the comics for their disappearance: they were all killed by Wolverine.

Let’s back up a bit, though, because it’s not really Wolverine’s fault. He was tricked by the master of illusions, Mysterio himself. The VFX specialist created his most demented mirage yet when he staged an attack on Xavier’s School for Gifted Youngsters. Under the impression that the compound was under assault from such feared villains like Doctor Octopus and Green Goblin, Wolverine slaughtered over 40 supervillains, all the while wondering what they had done to his fellow heroes, many of whom seemed to be missing.

But as he plunged his knives into the final villain, Bullseye, in his dying breath, asked him, "Why are you doing this? You’re supposed to be our friend." This is when Mysterio chooses to expose himself, revealing to Wolverine that he killed not a single villain, but rather all of his friends. Suddenly, Logan is able to see the people he’s killed as they truly are, and he gazes over the torn-apart corpses of Storm, Cyclops, and dozens of other heroes. This, Old Man Wolverine tells Old Man Hawkeye, is why he’s gone into hiding. He can never trust himself to be a superhero again.

It turns out Mysterio may be the evilest of all The Sinister Six.

Countless versions of The Sinister Six exist, many with more than six members

Sinister Six in Sinister War vol. 11

Well over a dozen teams have taken up the mantle of The Sinister Six, and in multiple instances had to change the team’s name to accommodate its expanded numbers. These supervillain cabals have spanned the multiverse and run the gauntlet of affiliated members.

Apart from the original Sinister Six on Earth-616, there have been versions on six other multiversal timelines, including the Sinner Six with Scorpio and Hydro-Man, the Insidious Six carrying Kingpin as its leader and boasting Shocker and Rhino as members, and the Norman Osborne Six, which blackmailed Spider-Man into joining them by threatening Aunt May. (Is Spider-Man even the Sinister Six’s real target? These guys really have it out for Aunt May, it would seem.)

In "Marvel Knights Spider-Man," our red-and-blue spandex-wearing hero squares off against the Sinister Twelve, also organized by Green Goblin. It might not have the same alliterative ring to it, but 12 villains are undeniably more threatening than a mere six, especially since Osborne managed to recruit Lizard, Boomerang, and Tombstone.

"Ultimate Spider-Man" dealt with the Ultimate Six, led by Green Goblin alongside Doc Ock, Kraven, Electro, Sandman, and Vulture. Many fans have speculated that this is the version we will most likely see join the MCU via the upcoming "Spider-Man: No Way Home." But no matter which group Spidey faces down in upcoming films, it’s sure to be his biggest challenge yet.