How great is Spider-Man? Six of his worst villains teamed up to beat him because they couldn't do it on their own. The Sinister Six easily ranks as one of the top super-villain teams in all of comics, and for good reason. Time and again, they've proven to be relentless in their goal of defeating Spider-Man.
Though the line-up - and the numerical value - fluctuates over the years, that fierce determination on the part of superpowered, genius-level grown men to beat a teenager at any cost never abates. Here are the ten worst things the Sinister Six has ever done to Spider-Man, ranked.
10 Kidnap Betty Brandt And Aunt May
With the Sinister Six, it's best to start at the beginning. Especially since the least-worst thing they did is really the first thing they did. The Sinister Six exists entirely because Doctor Octopus loses to Spider-Man three battles in a row, and he just can't accept it. He pulls together a Dream Team of Spidey villains including Mysterio, Kraven The Hunter, Sandman, Electro, Vulture, and rather than just dogpile him right from the start they decide to kidnap Betty Brandt and Aunt May, but the Six think she's just a bystander. Baby steps.
9 Turns Sandman To Glass
A bit later in the ongoing war between Spider-Man and the Sinister Six, Sandman has had enough. He reforms himself and actually helps Spidey defeat the Sinister Six. Naturally, the others aren't too happy with that and when they come to blows again over the destruction of some apartment buildings, Doc Ock uses the opportunity to turn Sandman into glass. This removes a potential ally from Spider-Man's arsenal and at a time when Doc Ock has significantly upgraded his. Worse for Sandman, the new Sinister Six wants to shatter him.
8 Destroys The Masters Of Evil
More recently, Doctor Octopus had control of Peter Parker's body and was the Superior Spider-Man. While he continued to masquerade as the hero, he also organized a new supervillain team because that's just how he rolls. The Superior Six get into a confrontation with the Masters of Evil over some machinations involving a character called Sun Girl, but the main thing is that the Superior Six - led by Spider-Man - absolutely destroys the Masters of Evil proving how truly dangerous they are.
7 Sinner Six
In an alternate reality (Spider-Man: Reign) on Earth-70237, the Sinister Six are the Sinner Six, and they are much more terrifying. This story has just a few echoes of The Dark Knight Returns.
It's thirty years in the future, Spider-Man is retired, and New York City is under the absolute control of the corrupt and unjust Mayor Waters. Waters himself reforms the Sinner Six and tasks them with the mission of killing Spider-Man. If they do, they can leave the city free to do as they please.
6 Stole A Guy's Head
If the Sinister Six can turn a guy into glass, there probably isn't anything they won't do. They proved that beyond the shadow of a doubt when they stole the head of Silvio Manfredi. Silvermane, as he was called, was mostly a street-level crook working for the Kingpin. And then he became a robot.
This actually happened because Silio was selling bad drugs and some teenagers who would turn out to be Cloak and Dagger thought these drugs gave them their powers. He becomes a robot, loses his head, which the Sinister Six steal as a totem to increase their power. This sets off a war in the criminal underworld that naturally Spider-Man has to deal with.
5 Forced Spider-Man To Join Them
Things in the Ultimate line of Marvel Comics generally got cranked up compared to mainline continuity. This played out the same for the Sinister Six, called the Ultimate Six in this universe. They coerced Spider-Man into joining the group - prefiguring the Superior Six in some ways - while also echoing the past. Peter believed that Aunt May had been kidnapped and if he didn't work with the villains, she was going to die. Spidey eventually beat them with the help of the Ultimates and discovered that Aunt May was just fine. She usually is. The woman can't die. She can, but not for long.
4 The Insidious Six
Concerns about what was too much for kids watching Spider-Man: The Animated Series led creators to change the name of the team from 'sinister' to a word kids probably didn't understand - 'insidious.' Rather than Doctor Octopus forming the team as in the comics, in the show, it's the Kingpin. The change shows - their tactics are a bit more brutal. May is kidnapped - again - and the team actually succeeds in capturing and unmasking Spider-Man. The only problem is they can't believe he's Peter Parker.
3 Kidnaps Aunt May (AGAIN)
The Sinister Six starts to go viral in the worst way after losing to Spider-Man again and again. What started with Doc Ock calling up his buddies turned into the Sinister Six calling up theirs and eventually you get the Sinister Twelve. This team is formed bu the Green Goblin from inside his prison cell.
Their radical solution to defeating Spider-Man once and for all? That's right. Kidnap Aunt May. Again. This time it's to force Spidey to break Norman Osborn out of jail. Hopefully, this is a trope the comics avoid going forward and the films avoid altogether.
2 Pick One
So, kidnapping Aunt May hasn't worked. Stealing the head of another villain hasn't worked. Obviously the next logical step is to change the gravitational field of the Earth. This one is a doozy, involving Doc Ock's need to be remembered as a hero and Chameleon's pretending to be Al Gore - really - but it ends with Spider-Man and Silver Sable trapped in an underwater base. Spider-Man is given a choice - fight Doc Ock and save Sable, or let her drown and save the world. Sable convinces Peter to let her drown. She got better, though.
1 Made Spider-Man Save Their Butts
During the Clone Saga, there were a few different Spider-Men running around. One of them was Kaine, the Scarlet Spider, who decided this Sinister Six business was for the birds and started killing them off. He succeeded in killing Doctor Octopus and Kraven's son, the Grim Hunter. The others joined together to fight off Kaine but Peter Parker had to intervene to keep them all from killing each other. After kidnapping Aunt May more times than he could count, saving his sworn enemies was the ultimate indignity.