The Sinister Six is usually considered to be a collection of Spider-Man's deadliest foes. Unfortunately, there have been versions that have been less than effective at striking terror. Sometimes, their assembly and defeat have even been off-panel.
Not included in the menagerie of rosters is Arcade's Sinister Sixty-Six, which were all holographic duplicates. Other versions of the Sinister Six have used varying numbers, like twelve and sixteen, but those retain the designation as parts of this villainous assemblage. Among the various members, some don't deserve to be counted among Spider-Man's deadliest foes.
10 Grim Reaper Isn't Even A Spider-Man Villain
In Civil War #2, by Mark Millar, Steve McNiven, and Dexter Vines, the issue opens with SHIELD coming across a beaten and detained Sinister Six. This assembly isn't even given the decency of a visible conflict. They're just described as being defeated by Captain America's allies opposing the Registration Act.
Grim Reaper is only on this team with Vulture and Melter because he escaped from the raft with them. He's better known as an Avengers foe. Specifically, he's targeted Wonder Man and the Vision.
9 Isn't The Melter An Iron Man Villain?
When the superheroes are on the lookout for escaped supervillains, maybe limiting the membership to Spider-Man foes isn't an option. The Melter was mentioned in Civil War #2 but wasn't shown with the Sinister Six until Spider-Man and the X-Men #4. With a group so clearly recognized with Spider-Man, though, it seems odd to have an Iron Man villain on the team.
Iron Man has elevated himself past as basic a villain as the Melter. This criminal is essentially a guy with a souped-up welding torch. He's fallen since his days with the original Masters of Evil.
8 Living Brain Is A Computer
The Living Brain is a Spider-Man foe from back in Amazing Spider-Man #8, published in 1964. While it was the most advanced computer possible in 1964, it's outdated in the 21st century. It's no surprise that in the time it was part of the Sinister Six, it was the first defeated and captured.
This was at the beginning of Doctor Octopus's time in control of Spider-Man's body. He turned the Sinister Six's attacks onto the Living Brain. He then reprogrammed the villainous supercomputer into a lab assistant.
7 Overdrive Can Transform Cars, But Nothing Else
Overdrive is a supervillain that controls nanites capable of restructuring vehicles. He's been little more than a joke, even revealing himself to be a fan of Spider-Man. His failure as a criminal has left him at the service of Mister Negative.
His choices in vehicles to commandeer are questionable at best. He converts the villain Big Wheel's titular vehicle and a school bus, with children still on it. Despite being a reliable member of Boomerang's Sinister Six, he almost always came across as a joke, even among his teammates.
6 Putting Hydro-Man On A Team With Sandman Invites Disaster To Repeat Itself
Norman Osborn put together a large Sinister Six team to break him out of prison. That got fleshed out with several tough Spider-Man villains. Among them were two villains that had worked together before, perhaps longer than they wanted to be.
Sandman is a stalwart past member of the Sinister Six, but Hydro-Man is not. Those two had worked together before and ended up being fused into a mindless "mud-thing." Norman Osborn didn't know about it.
5 The Owl Should've Taken The Hint From Constant Failure
The Owl worked with Boomerang to create a "Sinister Sixteen" to steal from the Chameleon. Boomerang double-crossed the Owl, who was out a lot of money to hire a dozen d-list super-criminals. Of course, the Owl was never one to catch a hint, even when the universe offered it up.
The Owl was routinely stopped by Daredevil, Black Widow, and even the Cat. He then caught a rare disease that paralyzed his legs. His later torment of Daredevil even resulted in him being beaten mercilessly by the hero, who believed his best friend had been killed.
4 Armadillo Was Recruited To Be A Distraction
As part of the Owl's Sinister Sixteen, the Armadillo was hired to provide the distraction while Boomerang stole a valuable painting from the Chameleon. On paper, the Armadillo seems very formidable, but his power and armor make him slow and clumsy. This is why he always seems to be on the losing side of any altercations.
With the others, he did a fine job of occupying the Chameleon's gang. Unfortunately, once Boomerang and his closest allies obtained the painting and other valuables, all the decoys could do was surrender to the police. It also seems that the painting was fake. The valuables in the safe behind it were the real target.
3 The Clown Should've Stayed In The Circus Because Owl & Boomerang Set Him Up To Take A Fall
Another d-list villain is the Clown from the Circus of Crime. This version is the most recent since the original gave it up to become a Gamma-powered villain. Like the original, he's violent, nasty, and possesses absolutely no powers.
The Circus of Crime has a decent gig, although it's gotten less and less successful over the years. Roll into town under various names, rob the circusgoers, and leave town with their ill-gotten goods. By accepting the Owl's offer to join the Sinister Six, he put himself in a no-win position.
2 The Kangaroo Is A Villain Whose Name Doesn't Strike Terror
Not every idea in the early years of Marvel was a winner. Among the ones that constantly show up on bad villains is the Kangaroo. After the original Kangaroo was killed, another trained, got special equipment and took up the mantle.
The special equipment that this new Kangaroo used didn't help him defeat Spider-Man. If it did, one could forgive the elements that make him look like a human kangaroo. Especially ridiculous are the long ears on top of his head.
1 8-Ball Is A Billiards-Themed Villain
Spider-Man took a position at the Jean Grey School teaching the young mutants about the responsibilities of being a hero. On one of their "field trips," he led them in stopping the Swarm's all-new Sinister Six from robbing a bank. Among the team was a criminal that struggles to be considered a d-lister, the billiards-themed 8-Ball.
8-Ball's costume is predominantly black with a spherical helmet that looks exactly like an eight-ball. His equipment includes a cue stick that strikes with heavy concussive force and ball-bombs. The mutant brain called No-Girl controls his body, attacking another member of the Sinister Six.