When it comes to iconic villains, few are as popular as the ones who’ve had to fight Spider-Man over the years. However, when six of them teamed up to take on the webslinger, it gave Peter Parker a challenge unlike anything before.

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The Sinister Six have been around for over 50 years, and have seen many different members join the fray, but every time they grace the pages of the comics, chaos ensues. If you’re unfamiliar with the team or want to know a bit more about them, we’ve put together everything you need to know about the Sinister Six.

10 Their First Appearance

In 1964, the Sinister Six made their first appearance in Amazing Spider-Man Annual #1. After multiple defeats at the hands of Spider-Man, Doctor Octopus thought that strength in numbers was the only way that Spidey would be defeated. Octavius contacted every villain that Spider-Man had ever faced, and the best of them heeded the call.

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Electro, Vulture, Sandman, Mysterio, and Kraven the Hunter joined forces with Doc Ock to concoct a plan to defeat their mutual enemy. Even without his powers (losing them after the death of Uncle Ben), Spider-Man managed to defeat each member individually, and the team split up shortly after.

9 It Took 25 Years Until They Returned

Sinister Six in Spider-Man TAS

After the original Sinister Six disbanded at the end of Amazing Spider-Man Annual #1, it would be a further 25 years until the team returned, making an appearance in Amazing Spider-Man #334. Unlike the first time they bumped heads with Spider-Man, they decided to attack him together, but due to Doc Ock’s betrayal earlier on (having ulterior motives for getting the band back together), they split up.

The team ended up joining forces with Spider-Man to defeat the common enemy they had in Octavius. They weren’t separated for long, however, and the dysfunctional team were back on the search for Spider-Man once more.

8 There Have Been Many Different Line-Ups Over Time

Spider-Man probably has the most villains of any Marvel superhero, so it was inevitable there would be multiple enemies wanting to join the Sinister Six. Hobgoblin was the next to join, but after more losses the team grew stronger with the likes of Beetle, Shocker, Chameleon, Venom, Green Goblin, Rhino, Hydro-Man, Lizard, and Boomerang joining at different points throughout the comic’s publication.

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No matter the motivation, the dysfunctional nature of the group often resulted in multiple fallings-out, so even though there have been lots of members, the Six have never managed to be significantly stable enough to defeat their sworn enemy.

7 Larger Teams Of The Sinister Six Have Existed

The Sinister Six

You’d have thought six enemies should be enough to take down Spider-Man, but over the years there have been more than six. The Sinister Seven was formed by Hobgoblin to take out Kaine Parker – a botched clone of Spider-Man – and the Sinister Twelve were formed by Norman Osborn after his imprisonment on being outed as the Green Goblin.

There was even a Sinister Sixty-Six formed by Chameleon and Mojo, that saw many of Spidey’s enemies as holographic forms battle it out with him in at the Xavier Academy. However, the bigger the team, the lower the calibre, and these outings had Marvel include some of the comic’s poorer villains.

6 Marvel’s First Crossover Involved The Sinister Six

Marvel comics have seen epic crossovers over the years, and in many story arcs there are familiar names popping up here and there. However, it was The Sinister Six’s first appearance that saw Spider-Man crossover with various superheroes such as Iron Man, Thor, and Captain America.

Although they acted more as cameos and not part of the story, it hadn’t really happened before, and it became a theme for the comics going forward. Amazing Spider-Man Annual #1 heralded the first major crossover in Marvel’s history and made way for the better-known crossovers such as Secret Wars, Civil War, and Crisis on Infinite Earth to follow in its footsteps.

5 They Tried To Destroy The World

In the Ends of the Earth story arc written by Dan Slott, Doctor Octopus concocted one of his most fiendish plans of all time. With his newly created Octavian Lens, he had the power to burn the Earth – essentially accelerating the effects of the Greenhouse Effect – and it leads to a race against time for Spider-Man and his allies.

Running from Amazing Spider-Man #682-687, the story sees The Avengers, Big Hero 6, and S.H.I.E.L.D. team up to take on the Sinister Six as well as other enemies like Crossbones and Lady Deathstrike, showcasing one of the most exciting Spider-Man stories of all time.

4 An Alien Was Once Part Of The Sinister Six

The Savage Land is known for being the home of Ka-Zar, as well as the source of Antarctic Vibranium, but it was also where we were introduced to Gog. In Amazing Spider-Man #103, J. Jonah Jameson, Peter Parker, and Gwen Stacey head to the Savage Land. It isn’t long before Gog appears and kidnaps Gwen, taking her to Kraven where he plans to make her the queen of his new world.

He was later sent to another dimension, but Doctor Octopus rescued him, finally recruiting the alien warrior to join the Sinister Six. Gog ends up being set back to the dimension he came from by Mister Fantastic, and unfortunately never really made the impact he'd hoped for as the Six’s final member of their third iteration.

3 The Avengers And X-Men Were Once Members

Avengers Endgame Cast Civilian clothes

Although the Avengers began the Ends of the Earth story arc fighting beside Spider-Man, Doctor Octopus used his infinite genius and allowed his mind control techniques to turn the Earth’s Mightiest Heroes against him, as Avengers such as Captain America, Hawkeye, Spider-Woman, and Iron Man turned on him.

In the Sinister Six’s first appearance in 1964, Mysterio created robots in the vision of the X-Men, but Spider-Man managed to destroy the faux mutants. Although they weren’t technically classed as members, both the Avengers and X-Men did fight for versions of the Sinister Six in one way or another, providing the most left-field iterations of the super villain faction.

2 Spider-Man Wasn’t Their Only Enemy

Spider-Bite swings with Spider-Man

The Sinister Six are most commonly seen battling Spider-Man, but there have been instances when their focus has been on other characters within the Marvel Universe. As mentioned earlier, they went after Kaine Parker when they found that his motivation was to kill all of Spider-Man’s villains, but they’ve also gone after former friends Chameleon and Sandman.

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In a weird turn of events, Doctor Octopus once became the Superior Spider-Man after his consciousness transferred to Peter Parker’s, and he faced the newest iteration of the Sinister Six, made up of Boomerang, the Living Brain, Beetle, Overdrive, and Speed Demon.

1 The Sinister Six Were Good Guys Once

When Doctor Octopus was the Superior Spider-Man, he formed a new group of heroes consisting of the original members of the Sinister Six after almost giving into his violent outbursts and killing Boomerang. With Chameleon replacing the deceased Kraven – now known as the Superior Six, their goal would be to fight for justice.

Thanks to Octavius seeing the memories of the now deceased Peter Parker, and the famous mantra of great power and great responsibility now emblazoned in his brain, they would face a great challenge in a new version of the Sinister Six. With Doc Ock controlling their minds, they went up against the Masters of Evil, and with the help of Sun Girl, managed to defeat Lightmaster. However, Octavius lost his hold over his allies, and the Superior Six were no more.

NEXT: Superior Octavius: How The Spider-Man Villain Became A Hero