In the first Marvel Legacy era issue of Spider-Man, Brian Michael Bendis and Oscar Bazaldua depict Miles Morales taking on a brand-new Sinister Six, with the membership consisting of Sandman, the new Electro, Spot, Hobgoblin, Bombshell and the mysterious new Iron Spider.

Bendis has described the team as being like "a real old-school, Oceans' Eleven crew of criminals. All of them have a very specific skill set, and there is a whale of a score that needs all six of them. It’s a doozy. I can’t wait for you guys find out what the Sinister Six wants. But the story will be very personal when people find out who the Iron Spider is."

So with the new Sinister Six finally making their debut, we thought it was the perfect time to look back at the long and complicated history of the villainous team within the Spider-Man comic book universe.

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In many ways, the very first Amazing Spider-Man Annual in 1964 is one of the most tremendous testaments in existence to the stunning early work of Steve Ditko and Stan Lee on their creation, the Amazing Spider-Man. We say this for two major reasons. One, Steve Ditko somehow remarkably drew this 41-page story (plus 30 pages of pin-up posters of Spider-Man's major villains and a couple of short stories explaining how Spider-Man's powers and webs work) while maintaining his regular schedule on the Amazing Spider-Man comic book series and two, because in just a little over a year, Ditko and Lee had introduced enough classic villains to put them together onto a six-member supervillain team!

That's just a remarkable achievement by any standard. The annual itself, though, is just a bit of goofy fun. After escaping from prison, Doctor Octopus decided to put together as many former Spider-Man villains as he could to form a new team. Since they ended up with six, they became the Sinister Six. The original lineup was Doctor Octopus, Electro, Sandman, Kraven the Hunter, Vulture and Mysterio. The issue was that each man wanted to defeat Spider-Man on their own to prove to themselves that they could do it. So Octopus worked out a system where they each would attack Spider-Man in randomly determined order and each man would wear Spider-Man down a bit for the later members. He held Aunt May and Betty Brant hostage and forced Spider-Man to go through the guantlet to rescue them.

The issue was noteworthy for the fact that Ditko did a full-page splash for each fight. Here are the first two, from the Electro and Kraven fights...

The issue also featured cameo guest-appearances by almost all of Marvel's major heroes of the era.

In the end, after he had defeated them all, Spider-Man even mocked the villains for not attacking him all at once...

In a fun bit of "remember, these stories were over 50 years ago," Aunt May is mostly irritated that she missed the newest episode of the Beverly Hillbillies while being held hostage by Doctor Octopus. At the end of the issue, Octopus has a new plan but the other villains no longer believe in him, thus severing their relationship and disbanding the Sinister Six. Remarkably, the team would then be defunct for over 25 years!

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It would not be until Amazing Spider-Man #334 (by David Michelinie, Erik Larsen and Mike Machlan) that Doctor Octopus would begin to put the team together again in a six-part storyline that was one of those bi-weekly six-issue storylines that were so popular at Marvel in the early 1990s on their most popular titles...

It took a few issues for Doctor Octopus to collect his team, which included all of the original members of the team (with Sandman, who had reformed, being forced into working with the team after Doc Ock threatened the family whose boardinghouse he lived at) except Hobgoblin replacing Kraven the Hunter, who had died a few years earlier.

This time, the team actually attacked Spider-Man all at once. In the end, though, Doctor Octopus betrayed his teammates and they ended up having to team up with Spidey to take Doctor Octopus down.

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Erik Larsen then wrote a sequel six-part story called "The Revenge of the Sinister Six" as part of his farewell performance as the writer/artist on Spider-Man before leaving Marvel to launch Savage Dragon at Image Comics. The other members of the team tried to get their revenge on Doctor Octopus for his earlier betrayal...

However, he convinced them to work with him on a new plot. He quickly got rid of Sandman, however, leading the team to need a new member. That turned out to be the gigantic being known as Gog...

This led to a tremendous conclusion where Spider-Man and a bunch of superheroes ended up taking on (and defeating) the newly complete Sinister Six...

A few years later, the mysterious Kaine (who turned out to be a failed clone of Peter Parker) began murdering Spider-Man villains, with the most prominent one being Doctor Octopus. In Spider-Man Unlimited #9 (written by Tom Lyle and drawn by roughly 314 artists), Hobgoblin put together a new Sinister Six team (technically the Sinister Seven) with himself, Electro, Vulture, Mysterio, Scorpia, the Beetle and the Shocker to hunt down Kaine to avenge their fallen comrade...

A few years later, Spider-Man's titles all ended and re-launched as just two titles, both written by Howard Mackie. There was Amazing Spider-Man, drawn by John Byrne (who likely had a say in the plotting of the series) and there was Peter Parker: Spider-Man, drawn by John Romita Jr. Soon into this run, Sandman was turned back into a villain. He then formed a new Sinister Six consisting of himself, Mysterio II, Electro (rocking the short-lived outfit he had gained during Byrne's Spider-Man: Chapter One series), Kraven's son, the then-current Kraven the Hunter, Vulture and new member, Venom...

Venom ended up turning on his teammates very shortly into their team-up, making this one of the shorter-lived Sinister Six teams.

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During Mark Millar's Hush-like one-year stint on Marvel Knights: Spider-Man (with Terry and Rachel Dodson), he had Norman Osborn hire the Scorpion to put together a new team to help him once Osborn forced Spider-Man to break Osborn out of prison after Osborn had Scorpion kidnap Spider-Man's Aunt May. The new team was dubbed by Osborn (now in his Green Goblin gear) as the Sinister Twelve, with the members being Green Goblin, Vulture, Sandman, Electro, Chameleon, Lizard, Hydro-Man, Shocker, Hammerhead, Boomerang, Tombstone and Scorpion, only Scorpion had just recently become the new Venom...

Probably the most embarrassing incarnation of the Sinister Six was the one that formed during Civil War consisting of Doctor Octopus, Grim Reaper, Lizard, Shocker, Trapster and Vulture (what an odd collection of villains - Grim Reaper isn't even a Spider-Man villain!) that was defeated off-panel in Civil War #2 (by Mark Millar, Steve McNiven and Dexter Vines)...

The most stable Sinister Six team, though, was soon to debut!

At the end of the "Spider-Man Brain Trust" era of Amazing Spider-Man, where the book was released three times a month and was written by a group of writers who would each take different arcs, Doctor Octopus put together a whole group of supervillains to help him hunt down a baby that he believed to be Norman Osborn. After that storyline ended, a new era in Amazing Spider-Man launched, where one writer, Dan Slott, would write the book on a bi-weekly basis. The first arc was dubbed "Big Time."

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In Amazing Spider-Man #648 (by Dan Slott, Humberto Ramos and Cesar Cuevas), five of those supervillains that Doctor Octopus had put together stuck around to form a new Sinister Six. They were Electro, Chameleon, Mysterio, Sandman and Rhino.

This incarnation of the Sinister Six would clash with Spider-Man a number of times over the next year or so, before finally coming to a culmination in the "Ends of the Earth" event, where they teamed up with Doctor Octopus to threaten to destroy the Earth itself...

After Doc Ock's ultimate plan to destroy the world was revealed, Mysterio agreed to help Spider-Man, but then a "new" Sinister Six debuted! Doctor Octopus had taken over the minds of six of the Avengers!

Spider-Man and his allies ultimately defeated the Avengers version of the Sinister Six and foiled Doctor Octopus' plot. However, a more successful plot was then launched by Doctor Octopus soon after where he succeeded in taking over Spider-Man's body and leaving Spider-Man to die in Doctor Octopus' old body. Before he died, though, Spider-Man forced Doctor Octopus to become a superhero by overloading him with Spider-Man's memories, which contained the heart of Spider-Man's mantra, "With Great Power Must Come Great Responsibility." So Doctor Octopus agreed to become a hero, but he decided he would be even better at being a hero than Spider-Man. He would prove himself to be the Superior Spider-Man!

In the first issue of his Superior Spider-Man series, Boomerang formed a new Sinister Six team consisting of himself, Speed Demon, Beetle (the newer female one), Shocker, Overdrive and the Living Brain...

"Spider-Man" was greatly offended by this new team and almost beat Boomerang to death before a vestige of Peter Parker's mind managed to hold him back...

That team, minus the Living Brain, soon got their own series by Nick Spencer, Steve Lieber and Rachelle Rosenberg...

That team briefly added Armadillo, Bi-Beast, Clown, Cyclone, Human Fly, Kangaroo, Man Mountain Marko, Mirage, Scorcher, Shriek, Spot and Squid to become the Sinister Sixteen...

"Spider-Man" (still controlled by Doctor Octopus) also put together a new, so-called Superior Six, which consisted of the original members of the Sinister Six (with Kraven replaced by Chameleon) just mind-controlled by Spider-Man. They debuted in Superior Team-Up (by Christoper Yost, Marco Checchetto and Rachelle Rosenberg)...

So yes, for a brief period in time there, there were actually competing Sinister Six teams in play.

Since everything in comic books has to get bigger and bigger, in the series, Spider-Man and the X-Men (by Elliot Kalan, Marco Failla and Ian Herring), Spider-Man (who had agreed to teach a class of students at the Jean Grey School for Higher Learning as a favor to his dead friend, Wolverine) and his students got kidnapped by Mojo and then forced to fight against a group of villains based on Spider-Man's various foes, dubbed the Sinister Sixty-Six!!

Oddly enough, that wasn't the only Sinister Six-related team that appeared in that particular series! After they had returned to Earth, Spider-Man and his students then ran afoul of a new Sinister Six that was formed by Swarm, the Nazi Scientist who is now made up entirely of bees! Consisting of D-List Spider-Man villains Delilah, Squid, Killer Shrike, Melter and 8-Ball to go along with Swarm, they appeared in Spider-Man and the X-Men #4 (by Elliot Kalan, RB Silva, Rob Lean and Ian Herring)...

Hilariously enough, Kalan decided to take the joke one step further in the final issue of that series, Spider-Man and the X-Men #6 (by Kalan, Marco Failla, Diogo Saito and Ian Herring), where Mister Sinister formed a new team of underlings in cloned bodies of members of the X-Men. The clones were of Beast, Iceman, Wolverine, Nightcrawler, Jean Grey and Storm (Storm's clone had No-Girl in control of her body). His new team was dubbed "Sinister's Six"...

An interesting side-note to the Sinister Six is that, by virtue of their name, they only consist of six members and naturally, that limits them (despite the times that they have formed larger teams, anyway). This led to Tom DeFalco and Ron Frenz introducing a new take-off on the idea of a supervillain team with the Sinister Syndicate in Amazing Spider-Man #280...

That team has had larger memberships over the years, since they were not limited by the "six" part of the name.

In any event, the Sinister Six set-up has been a longstanding part of Spider-Man's history. There was even an Ultimate Universe version that fought the Ultimate Spider-Man before Miles Morales took over!

So it is interesting to see the team move forward to becoming part of Miles Morales' history, as well, staring with last week's Spider-Man #234...