Amazing Spider-Man Annual #1Insidious: Spider-Man Villain Team-Ups by Jerry Whitworth


Among the various rogues galleries of fictional characters, Spider-Man has one of the largest and most varied set of enemies in history. Even more dangerous, many of Spider-Man’s villains take little issue with organizing into a group to combat him. The first, and most prolific, such group is the Sinister Six. Formed in 1964’s Amazing Spider-Man Annual #1, Doctor Octopus was confidant where one villain failed to destroy Spider-Man, a group could finally do away with him. Contacting Doctor Doom, the Lizard, Green Goblin, Sandman, Electro, Vulture, Mysterio, and Kraven the Hunter, the last five answered the summons and formed the Sinister Six. In order to keep from stepping on each others toes, Octopus broke up the six members in different locations advantageous to the villain’s skills and abilities and lured Spider-Man into playing the game by kidnapping the Daily Bugle’s Betty Brant and Peter Parker’s Aunt May (the latter caught up when she went to the Bugle looking for her nephew). Of course, Spider-Man wins the day and triumphs over his enemies. The group would retire for almost three decades. In that time, several villain teams cropped up.


Amazing Spider-Man #280Over in Japan, Toei’s Spider-Man would face the Iron Cross Army lead by Professor Monster with Amazoness, Bella, the Ninders, and the Machine Bem. In America, the Sinister Syndicate was a mercenary group patterned after the Sinister Six made up of Spider-Man villains. Lead by the Beetle who brought together Hydro-Man, Rhino, Boomerang, and Speed Demon, the Sinister Syndicate was hired to protect the first Jack O’Lantern in Jason Macendale who was sought by Spider-Man and the mercenary Silver Sable. Successfully protecting Macendale, the Syndicate failed to kill their former foe due to the help, of all people, of Sinister Six founder Sandman. The Sandman began to reconsider operating as a villain after a cancer scare and traumatic experience merging with Hydro-Man to form the Mud-Thing. Separating back from his fellow Spider-Man villain, Sandman had a heart-to-heart with the Fantastic Four’s the Thing (Sandman a founding member of the malicious Frightful Four battling the team of heroes) and decided to turn his life around. The former villain infrequently teamed with Spider-Man and soon after saving her, Sable decided to hire Sandman and formed the Outlaws (superhumans used to combat superhumans). Spider-Man having the unique distinction of many of his enemies reforming towards good, the Outlaws saw several former Spider-Man enemies group into a band of mercenaries with more altruistic motives. Alongside Sandman, there was Will o’ the Wisp, Puma, Prowler, and Rocket Racer. When the Space Phantom initiated a conflict between Spider-Man and the Avengers, the web-slinger called in the Outlaws to help him in the situation. Following a Presidential pardon for the Sandman, the former villain and Spider-Man would be inducted into the Avengers as reserve members.


Amazing Spider-Man #338During the event Acts of Vengeance, Loki convinced Doctor Doom, Kingpin, Magneto, Mandarin, Red Skull, and the Wizard to form a cabal to eliminate their enemies in a united effort (though approached, Apocalypse, Cobra, Mad Thinker, and Prince Namor the Sub-Mariner declined). To further this plan, Loki broke the various supervillains imprisoned in the Vault out of their confinement. Kingpin worked with Doctor Doom against Spider-Man pitting Goliath against the hero and the Wizard used the Dragon Man against webhead but Spider-Man was victorious thanks to the cosmic powers he obtained as Captain Universe. Following Acts of Vengeance, Graviton frees the Brothers Grimm, Titania, and Trapster who team with Goliath and are hired by the Chameleon for one hundred thousand dollars each to eliminate Spider-Man. Despite some early success, Spider-Man ended up successful in halting the villain group. The following issue, reformed villains Molten Man and Green Goblin (Harry Osborn) teamed up with Spider-Man against the villainous Tombstone. Spider-Man’s original group of rogues in the Sinister Six would reform around this time. Doctor Octopus reforms the Sinister Six by threatening to slay the family Sandman is boarding with should he refuse and replacing Kraven (who had committed suicide) with the Hobgoblin (Jason Macendale). Octopus plotted poisoning the world in order to take over the Earth only for Sandman to betray him and join Spider-Man in defeating Doc Ock. For revenge, Octopus turned Sandman into glass only for Spider-Man to save him (Sandman was previously turned to glass by the Mandarin when they teamed against the Hulk). The story’s title, “Spider-Man: Return of the Sinister Six,” would be used for a video game two years later around the time of the publication of the “Spider-Man: Revenge of the Sinister Six” storyline.


Maximum CarnageFollowing the return of the Sinister Six, the Sinister Syndicate would again trouble Spider-Man in the pages of The Deadly Foes of Spider-Man. The Kingpin hires the Beetle to reform the Syndicate to rob the Federal Reserve who are joined by (believed-deceased) supervillain the Ringer’s wife (and Boomerang’s current girlfriend) Leila Davis. However, Davis blames Beetle for the death of her husband and recruits Boomerang, Rhino, and the Shocker in getting revenge on their former leader. Just as it seemed Davis would get vengeance upon the Beetle, Spider-Man intercedes and saves his life. Shortly afterward, the Sinister Six would yet again reform. Good to his word, Doctor Octopus murdered the family who took in Sandman (save the family’s matriarch) leading the villain-turned-hero to assemble the other members of the Sinister Six against Doc Ock (as the villain betrayed the others in his plot for conquering Earth). To be on the safe side, Sandman invites Spider-Man to act as back-up in case something goes wrong. In the exchange, it’s revealed Sandman’s four recruits were behind the massacre of the family Sandman was avenging who staged the attack to bring out Sandman where Octopus again turns him to glass and shatters his body. Spider-Man jumps into the fray and is saved by the timely appearance of the Hulk (whose group the Pantheon were on the trail of Octopus who obtained adamantium arms). The Sinister Five manage to escape and reform (with Electro revealed to have been hired by Octopus to set the whole plan into motion). Adding the alien Gog to their ranks and assembling an arsenal of weapons and army of robots from an alternate dimension, the Sinister Six threaten to conquer Earth but are stopped by the combined efforts of Spider-Man, Ghost Rider, Hulk, Nova, Solo, Deathlok, Sleepwalker, Fantastic Four, and a reformed Sandman.


Insidious SixShortly after defeating the Sinister Six again, Spider-Man would team with the New Warriors against Justin Hammer’s Hero Killers. Mercenaries hired to kidnap heroes, Sinister Syndicate members Beetle, Boomerang, Hydro-Man, Rhino, and Speed Demon were reunited alongside over half a dozen other villains. The following year, Spider-Man would have to face another team of his villains. Carnage, the murderous offspring of Venom, escaped Ravencroft Asylum freeing its other super-powered inmates to form a deranged family of killers. With Shriek as Carnage’s wife, they adopt Demogoblin and Carrion as their children and take on Spider-Man’s Doppelganger (from Infinity War) as their pet. Spider-Man would have to team with Venom, Captain America, Black Cat, Nightwatch, Cloak and Dagger, Iron Fist, Deathlok, Morbius the Living Vampire, and Firestar to bring the villains to justice. The story would be adapted into a video game. The Sinister Syndicate would again return, in a fashion, in The Lethal Foes of Spider-Man. Leila Davis, paroled from jail, adopts a suit of high-tech armor and takes the name Hardshell and hires Boomerang, Rhino, and the Vulture in gaining vengeance upon the Beetle. The team would steal an experimental gun from the U.S. Atomic Research Company making them a target of the Beetle, Stegron the Dinosaur Man, Swarm, the Answer, Doctor Octopus, and Strikeback (the believed dead villain Ringer rebuilt as a cyborg operative for A.I.M.). The mini-series title would inspire the name of the video game The Amazing Spider-Man: Lethal Foes two years later.


Spider-Man Unlimited #12Spider-Man’s imperfect clone Kaine would start killing off the hero’s enemies. Following the deaths of Kraven’s son Grim Hunter and Doctor Octopus, Hobgoblin (Jason Macendale) recruits Electro, Mysterio, Vulture, Beetle, Shocker, and Scorpia to form the Sinister Seven to hunt down and get Kaine before he could get them. The group would battle Kaine and almost kill him until Spider-Man arrived to save him leaving the duo to topple the group. The same year, the mid-1990s Spider-Man animated series would introduce its version of the Sinister Six. Despite Mister Sinister being a major antagonist on the X-Men animated series, television executives felt the word “sinister” was too scary for children and so the Sinister Six became the Insidious Six. Formed by the Kingpin and made up of the Chameleon, Doctor Octopus, Scorpion, Mysterio, Shocker, and the Rhino, the group was brought together to destroy their mutual foe. Slightly adapting the Sinister Six’s first appearance, Aunt May was kidnapped and used as bait only for Spider-Man to win out in the end. The group would be reunited again later by the Kingpin (with Mysterio replaced by the Vulture) to gain six keys to the Red Skull’s doomsday device. Combating Spider-Man (who was pulled into the conflict while trying to clear the names of his secret agent parents) and the Six Forgotten Warriors (Captain America , Black Marvel, Destroyer, Miss America, Whizzer, and Thunderer), the villain group successful but are betrayed by the Chameleon who helps the Red Skull use the device to give birth to Electro. A video game based on the animated series would feature the Syndicate Six with Doctor Octopus, Chameleon, Scream, Beetle, Hypnotia, and Electro.


Amazing Spider-Man #12The following year, the Daily Bugle posted a one hundred thousand dollar bounty on a skeleton in a Spider-Man costume photographed with Spider-Man (in reality, the remains of a Spider-Man clone planted by the Jackal). The Beetle, Boomerang, Shocker, Jack O’Lantern (Steve Levins), and Scorpia decided to form a group of rogues to cash in on the newspaper’s reward and attacked the hero. Happening in that same issue, Spider-Man Unlimited #12 (May 1996), it’s revealed several of Spider-Man’s rogues attend Villains Anonymous (aka Vil-Anon) in an effort to reform. Its members included Armadillo, Big Wheel, Equinox, Hypno-Hustler, Man-Bull, and the Schizoid Man. The following year, Spider-Man had to contend with the Spider-Man Revenge Squad (aka the Legion of Losers). Grizzly brought together the Kangaroo (Brian Hibbs), Spot, and the Gibbon with the purpose of gaining revenge against Spider-Man. The Spot and the Kangaroo instead wanted to rob a bank. The group would capture Spider-Man when he interrupted the robbery but Grizzly and Gibbon had a change of heart. When the Spot and Kangaroo wanted to kill the wall-crawler, their two partners battled and incapacitated them. Spider-Man had actually pretended to be defeated to give Grizzly and Gibbon the opportunity to make the right choice. Spider-Man took the two defeated villains to the authorities and the two reformed criminals became a crime fighting duo. The same year, several villains went down their own road of redemption. When the Avengers disappeared, a new team of heroes emerged called the Thunderbolts. In reality, it was Baron Zemo and the Masters of Evil in a ploy for power only for the members beneath Zemo to actually grow to like being heroes. Composed of Goliath, Beetle, Fixer, Moonstone, and Screaming Mimi, the villains became Atlas, MACH-1, Techno, Meteorite, and Songbird, respectively, as Zemo became Citizen V, most of the group has remained on the side of good for the most part.


Ultimate SixIn 1999, Adam-Troy Castro would begin seeing his novel series the Sinister Six trilogy published. Deeply engrossed in the Spider-Man mythos, the series features an extraordinarily wealthy and well connected man with a decades old grudge against the Parker family. Named Gustav Fiers, better known as the Gentleman, the elderly sadist, racist, sexist, nihilist, and worse facilitated the death of the Parkers when they had the misfortune of crossing swords with him in their capacity as intelligence operatives. For good measure, the Gentleman’s brother left evidence painting the couple as traitors to America. When Peter Parker cleared his parents name, the Gentleman returned with a plan to exact revenge on the youth and become perhaps the most powerful man on Earth. Recruiting the Chameleon, Doctor Octopus, Electro, Vulture, and Mysterio, the group formed a new Sinister Six under the Gentleman’s banner with his mysterious bodyguard/slave Pity (who Spider-Man believes is his sister). About the same time in the comics, the Sandman reemerged as a villain again working with the Wizard. The move came as a surprise for fans who had read stories of the character as a hero for almost two decades. Shortly afterward, it was explained the Wizard used a device to make Sandman evil again. Apparently, it also did something to his memory when he wanted to reorganize the Sinister Six to get revenge against Spider-Man and Doctor Octopus (who was resurrected by the Hand ninja clan), the latter for turning him into glass twice. Sandman brought together Electro, Vulture, Mysterio (Daniel Berkhart), Kraven the Hunter (Alyosha Kravinoff), and Venom (where Eddie Brock suffered amnesia and the symbiote twisted his mind back into a villain). The group would be defeated and Venom turned on his allies, seemingly killing Sandman and seriously wounding Electro and Kraven.


Sinister TwelveSome years later, Torus Games produced the video game Spider-Man 2: The Sinister Six featuring Doctor Octopus kidnapping Aunt May and reorganizing the Sinister Six with Mysterio, Sandman, Vulture, Scorpion, and Kraven. Marvel would also partner with WizKids the following year to produce HeroClix tabletop gaming based on its properties. One of the factions in the game was the Sinister Syndicate largely made up of Spider-Man villains. In 2003, following Spider-Man’s public unmasking, the Chameleon formed the Exterminators in order to kill his longtime foe. Hiring Electro, Rhino, Scarecrow, and Swarm and blackmailing Molten Man and Will o’ the Wisp (the former definitely and latter speculated in the Spider-Man: Back in Black Handbook), Spider-Man and the Black Cat defeated the group as Aunt May poisoned the Chameleon who was pretending to be Peter. Ultimate Spider-Man would get to face his Sinister Six that same year in the pages of Ultimate Six. When the Green Goblin, Doctor Octopus, Electro, Sandman, and Kraven the Hunter escaped from prison, Spider-Man joined the Ultimates to bring them to justice. However, the villain group captured Spider-Man and threatened to kill his loved ones if he didn’t join their ranks. The Ultimate Six attacked the White House where they battled the Ultimates and were defeated.


Spectacular Spider-Man Sinister SixSome years later in the Marvel comics proper, Norman Osborn (who it turned out did not die battling Spider-Man) returns to New York where he is unmasked as the Green Goblin and sent to prison. While in prison, Osborn contracts the Scorpion to kidnap Aunt May and organize Spider-Man’s villains. Threatening to kill his aunt if he didn’t break him free, Spider-Man with help from the Black Cat rescued Osborn who had his newly branded Sinister Twelve attack the duo. Scorpion had brought together Boomerang, Chameleon, Electro, Hammerhead, Hydro-Man, Lizard, Sandman (who turned up alive but wildly mentally unstable between the Wizard’s messing with his mind and his injuries caused by Venom), Shocker, Tombstone, and the Vulture while acquiring the Venom symbiote for himself as Osborn once again donned his Green Goblin persona. All hope seemed lost until the arrival of Captain America, Iron Man, Daredevil, Yellowjacket, and the Fantastic Four at the behest of Peter’s wife Mary Jane who suspected a trap and called S.H.I.E.L.D. The Goblin would flee with Mary Jane in tow and Spider-Man would battle him atop a bridge. In the end, Osborn was done in when Mary Jane shot him, he was struck by lightning, and was attacked by Doctor Octopus (who was brainwashed by the police). The following year, Boomerang, Hydro-Man, and Shocker teamed up against Spider-Man but fled when Komodo and War Machine showed up to inject Spider-Man with an experimental dart believed to suppress superhuman powers. Largely a homage to Batman: The Dark Knight Returns, Spider-Man: Reign told of a dystopian future where Spider-Man returns from retirement after a totalitarian government severely oppresses the people of New York. The mayor releases Electro, Mysterio, Kraven the Hunter, The Sandman, Scorpion, and Hydro-Man as the Sinner Six promising them they could leave the city should they defeat Spider-Man. The group defeats Spider-Man but he is saved by the tentacles of Doctor Octopus that survived his demise and brought the hero to his wife’s grave (Mary Jane dying of cancer brought on by Spider-Man’s radioactive semen).


The GauntletIn 2008, the animated series The Spectacular Spider-Man would premier and would feature its own Sinister Six. In this version, Doctor Octopus organizes Electro, Vulture, Sandman, Rhino, and Shocker to battle Spider-Man who at this time wore the alien symbiote black suit. That same year in the comics, following the magical dissolution of Peter Parker and Mary Jane Watson’s relationship (with Spider-Man’s identity again a secret), Spider-Man is framed for murder and Norman Osborn, head of the Thunderbolts (more or less becoming a new version of Freedom Force), sends his forces to capture the hero. Osborn leads Venom (Mac Gargan), Songbird, Radioactive Man, and Bullseye against the hero only for the timely intervention of Eddie Brock to save him (Brock, dying of cancer, sold the black symbiote but was later miraculously healed and when he came into contact with the symbiote again became instead Anti-Venom, his touch caustic to his old ally).


The Superior Foes of Spider-ManThe following year, Doctor Doom would hire the Sinister Six in the Marvel Adventures series Doctor Doom and the Masters of Evil. In the Marvel universe proper, Spider-Man would be dragged into a gang war between Mister Negative and the Hood. The latter had assembled a crew of supervillains mostly from Spider-Man’s pool of enemies including White Dragon and the Dragon Lords, Spot, Lightmaster, Answer, White Rabbit, Squid, Scorcher, Speed Demon, and Bloodshed. Later that year, Kraven’s daughter Ana Kravinoff and lover Sasha Aleksandra Nikolaevich attempted to resurrect Kraven and murder Spider-Man and all of his spider-kin. Towards this end, they enlisted the aid of the Chameleon, Diablo, Deadpool, Electro, a second Rhino, Mysterio (claiming to be the original who faked his own death), Vulture (Jimmy Natale), Scorpion (Carmilla Black), Lizard, and the newly resurrected Grim Hunter. Despite the resurrection of the original Kraven, Spider-Man and allies managed to defeat the villains at the expense of friends Mattie Franklin, Madame Web, and Kaine who lost their lives (the latter returning as a spider creature at story’s end). A year later, Doctor Octopus builds an organization of supervillains recruiting the Chameleon, Diablo, Electro, Freak, Hammerhead, Hippo, Lizard, Mister Negative, Morbius the Living Vampire, Mysterio, Overdrive, Rhino, Sandman, Shocker, Spot, Tombstone, Vermin, and Vulture (Jimmy Natale) in order to capture the child of supervillains Menace and Norman Osborn in hopes its blood could save his own life. However, the child proved to instead be of Menace and Norman’s son Harry and was then of no use to Octopus and the group fell apart. Following this, Octopus reforms the Sinister Six with the Chameleon, Electro, Mysterio, Rhino, and Sandman to slip his macro-octobot army into a military base and detonate it. The group is bested by Spider-Man, the Avengers, and Fantastic Four. Some time later, the group returns stealing technology from all around the world to form a device Octopus could use to ransom the Earth or see its destruction. Spider-Man and the Avengers combat the Six but Octopus turned on his allies again plotting to destroy the world since he did not have long left to live. Using his Octobots, Octopus enslaved the minds of Spider-Woman, Iron Man, Hawkeye, Black Widow, Captain America, Thor, and Red Hulk but Spider-Man, Silver Sable, and Mysterio managed to overcome them and stop the villain (though, it appeared at the cost of Silver Sable and Rhino who seemingly drowned fighting each other).


In the pages of Ultimate Spider-Man, the Green Goblin breaks Doctor Octopus, Sandman, Electro, Kraven, and the Vulture out of prison and reforms the Sinister Six. When Octopus decides he doesn’t want to kill the hero because of his hand in creating him, Goblin takes his life. The remaining group descended on Peter’s house and battled the Human Torch and Iceman (who were staying with their friend at the time). Parker arrived to join in the fray but Aunt May turned the tide when she arrived and gunned down Electro. Goblin escaped with Parker in pursuit and the pair had their climatic final battle resulting in the hero’s demise. The 2011 musical Spider-Man: Turn Off the Dark would introduce its own Sinister Six. Green Goblin would take his former employees and genetically modify them to create Carnage, Electro, Kraven the Hunter, Lizard, Swarm, and Swiss Miss. In 2012, Ultimate Spider-Man would be adapted into its own television series and would adapt the Sinister Six in its second season. In this version, Doctor Octopus brought the group together made up of Rhino, Kraven, Beetle, Lizard, and Electro. Also in 2012, Marvel Comics would relaunch much of its line as part of the Marvel NOW! promotion including Spider-Man in The Superior Spider-Man. In the title, Doctor Octopus switched bodies with his nemesis as Parker died in Octopus’ body. Early in this new role, Octopus defeats a new Sinister Six in Boomerang, Overdrive, Shocker, Speed Demon, Living Brain, and the Beetle (Janice).

 Our Sponsors – These products where hand chosen for you!