Peter Parker aka the Amazing Spider-Man has amassed one of the most colorful rogues galleries of any Marvel hero over the course of his sixty year superhero career. As formidable as the web-head's most iconic villains are on their own, it is when they come together that they are at their most effective.
Over the decades, Spider-Man has faced off against a plethora of supervillain team-ups, but none have been as indelible to his history as the Sinister Six. The supervillain team has gone through quite a few incarnations over the course of their history, and a few incarnations of the Six are much more memorable than others.
The Heroic Superior Six Version of Doctor Octopus' Sinister Six
The eighth incarnation of the team, better known as the Superior Six, was first brought together in 2013's Superior Spider-Man Team-Up #5 (by Christopher Yost and Marco Checchetto). Formed by Otto Octavius during his tenure as the Superior Spider-Man, the Superior Six were Otto's attempt to be a hero without having to ally himself with his former enemies.
Octavius instead called upon his old compatriots Electro, Sandman, Chameleon, and Vulture, as well as the the new and enigmatic Mysterion. Despite his relatively benevolent motivations, Otto was forced to employ mind control in bringing the team together on the battlefield, and as soon as he lost his grip, the team turned on him before disbanding.
Boomerang's Version of the Sinister Six
When no other villains were operating under the mantle of the Sinister Six, Frederick Myers, aka Boomerang, formed a new version of the team in 2013's Superior Spider-Man #1 (by Dan Slott and Ryan Stegman). Alongside Shocker, Speed Demon, Overdrive, Beetle, and the Living Brain, Boomerang carried out a series of crimes, purely for fun and profit.
Although this iteration of the Sinister Six was not the most dangerous, Boomerang's lineup did provide some of the most uproarious situations any version of the team has ever seen. This Sinister Six team was characterized by infighting among its members, oftentimes because of the actions of Boomerang himself, and was doomed to fail from the beginning. Despite their short lifespan, this Sinister Six did help to round out Boomerang before he became an important figure in Peter Parker's personal and professional life.
The Iron Spider's Version of the Sinister Six
Following the Multiverse shattering events of 2015's Secret Wars, Aaron Davis, aka the Prowler of the Ultimate Marvel Universe, was returned to life in the primary universe. Not long after, Aaron purchased a black market Iron Spider suit and took up that name as he returned to villainy.
In 2017's Spider-Man #234, Aaron revealed his new suit as well as his own Sinister Six team featuring Bombshell, Hobgoblin, Sandman, Spot, and Francine Frye's Electro. This particular team was formed in the hopes of heisting a decommissioned Helicarrier, yet they only succeeded in almost tearing one another apart. In the end, yet another Sinister Six was disbanded, though the experience was enough for Aaron to swear off his criminal lifestyle for good.
The Sinister Six Led by the Sandman and Featuring Venom
Led by Flint Marco, aka the Sandman, the fourth iteration of the Sinister Six was introduced in 1999's Amazing Spider-Man #12 (by Howard Mackie and John Byrne). Consisting primarily of former members such as Kraven the Hunter, Mysterio, Electro, and Vulture, this version marked Venom's first and only appearance as a member of the team.
Rather than being created to terrorize Spider-Man, this Sinister Six were formed under the pretense that they would be striking a fatal blow to Dr. Otto Octavius himself. Everyone who had worked with him previously believed Doctor Octopus to be the cause of many of their woes. Before their plan could come together, Venom turned on his fellow villains, nearly killing Sandman before the team fell apart completely.
The Sinister Six Formed by Kindred
The most recent version of the Sinister Six was brought together once more by Doctor Octopus, yet it was the demonic Kindred who was truly behind their formation. Having been promised another chance to be a hero, Octavius sought out Electro, Mysterio, Kraven, and Sandman at the demon's behest.
Along with a duplicate of the Lizard that was created by Kindred, Doctor Octopus and the new Sinister Six played a vital role during 2021's Sinister War. Apart from appearing during the final battle between a multitude of different anti-Spider-Man teams, this Sinister Six also went to war with Adrian Toomes' team, the Savage Six, as well as the Syndicate, Superior Foes of Spider-Man, and the Foreigner's Wild Pack.
Doctor Octopus' Original Sinister Six
As explosive as every Sinister Six lineup has been over the years, there is no version of the team as memorable as the original. Initially assembled in 1964's Amazing Spider-Man Annual #1 (by Stan Lee and Steve Ditko), the very first Sinister Six were brought together by Doctor Octopus in the hopes of finally putting an end to his losing streak against the wall-crawler.
Consisting of Sandman, Kraven, Electro, Mysterio, and Vulture, the original team launched a coordinated assault on Spider-Man, utilizing each member's unique talents in creative and unexpected ways. When this wasn't enough to bring down the web-head, the Sinister Six targeted those closest to him, including the Daily Bugle's Betty Brant. This convinced Peter to leap into action despite having recently lost his powers, somehow emerging victorious with little more than his wits. The first Sinister Six certainly weren't the most successful iteration of the team, but they set the bar for every subsequent supervillain team in the Marvel Universe to follow.