|Members|| Doctor Octopus|
Kraven the Hunter
- Doctor Octopus/Otto Octavius: The de facto leader of the Six who started the group. He bears powerful mechanical "arms" that are at his will.
- Electro/Max Dillon: An electrician at ESU who turned rogue after an accident endowed him with electrical generation and projection.
- Kraven the Hunter/Sergei Kravenoff: An accomplished big-game hunter who was transformed into a savage man-beast.
- Mysterio/Quentin Beck: An actor-turned-criminal that uses illusions and robots to confuse his enemies.
- Rhino/Alex O'Hirn: As well a former common criminal, who has amazing superhuman strength and an impenetrable armor-like suit.
- Sandman/Flint Marko: A former common criminal who has the enhanced abilities to turn his body into living sand and superhuman strength.
- Shocker/Montana: A former hit-man with vibro-shock units that can create super-sonic blasts of energy.
- Vulture/Adrian Toomes: An elderly former-scientist who has wings that allow him to have several aerobatics abilities.
Each member of the six once fought against Spider-Man and was defeated. All of them were imprisoned in New York State Prison, where each stayed for a series of times. All of them held a grudge against the wall-crawler, but for different reasons. Doctor Octopus contacted Electro, who was not incarcerated, and they concocted an escape plan to lead Doc Ock and select other villains out of the prison in order to team-up on their hated enemy.("Group Therapy")
Electro succeeded in turning off securities for the cells of Sandman, Rhino, Vulture, and Doc himself. They all therefore escaped, Ock leading the villains out of the prison, where Vulture, Shocker, and Doc Ock received their super-villain paraphernalia from Hammerhead and went into the city to lure and attack Spider-man.
Spider-Man had recently gained a symbiote that attached itself to his suit and granted him enhanced abilities.
The Six lured Spidey into Times Square and revealed themselves to him one-by-one; much to the Web-head's surprise and anxiety. They defeated him soundly, causing the frustrated Spider-man to escape by hiding in the sewers. Doctor Octopus, Shocker, Sandman, and Electro followed, but were unable to find him. They retreated to a local restaurant and celebrated what they thought was an inevitable victory. Each of the Six expressed their own desires for destroying him, and some threatened to quit the group, but Electro told them to trust in Doc Ock and they would all get what they wanted.
Later, the Six lured Spider-man again into Central Park, only this time Peter Parker was asleep, and the alien symbiote costume silently fought the villains, using Peter's body. Eventually the Spider defeated five of the villains, using their strengths and weaknesses against each other.
Rhino was taken out first, when he accidentally got in the way of Shocker and Electro's combined blasts. The Spider tossed the unconscious Rhino on top of Electro, then swung off as the rest arrived, wondering what had happened to Rhino and Electro. Vulture and Shocker tried to stop Spider-man from escaping, but Spidey took out Vulture by ripping apart his tech-flight circuitry. Spider-man took off Vulture's talons and used it to pierce one of Shocker's gauntlets. While Shocker and Spidey battled it out, Sandman came up from behind to knock out Spidey, but the Spider dodged both him and Shocker's blast, which punched a hole through Sandman. Spider-man pulled Shocker into Sandman, and the vibrations of the ruined gauntlet caused Sandman to disintegrate. Spider-man pulled off the gauntlet and dropped it on top of Sandman, so that he could not reform himself. Spidey then ripped off Shocker's other gauntlet, thus rendering him powerless.
Then Doctor Octopus, who was the only villain remaining, grabbed the tired out Spider and attempted to finish him off by impaling him on the unconscious Rhino's horn. The Spider escaped however, thanks to the desperate Electro giving off one last blast of electricity and zapping both Doc Ock and Spidey. After he recovered, Doc Ock noticed the symbiote suit, and noted his interest in examining it once he had killed Spidey. But with a few swift and powerful moves, the Spider easily knocked Octopus out, defeating the last of the Six. He was about to kill Doc with one of his own sharp pincers, but Captain Stacy arrived and told him it was over. Four of the Six were sent back to prison, and Electro and Doc Ock to Ravencroft, thus causing the team to dissolve. For the time being. ("Group Therapy")
A few months later, the Master Planner (aka Doctor Octopus) and his associate, the Tinkerer, arranged the reformation of the Sinister Six (this time explicitly named as such). Using an android stand-in for Quentin Beck (Mysterio), and a hologram of Adrian Toomes (Vulture), the guards were distracted enough so that Rhino and Sandman could once again escape.
The recently recruited Kraven the Hunter busted out Electro from Ravencroft, but Otto Octavius (who expressed his seeming regret at being a former super-villain) was unwilling to join them.
When the new Sinister Six were all together, the Master Planner relayed his plan to them, which was to fight Spider-man two at a time, so as to wear him down bit by bit. In the first wave, Electro and Vulture attacked Rockefeller Center, where Peter Parker and many of his friends were skating. Spider-man was at first expecting the entire Six to show, but was surprised to see that only Vulture and Electro were there.
After easily taking out Vulture, Spider-man lured Electro away to a tire barn, where he defeated Electro by trapping him in melted rubber. Spidey didn't get a break however, as soon after, Sandman and Rhino attacked.
After a few brutal beatings from the two, Spidey lured them to the pier, where he doused Sandman with a hydrant and froze him, then sent Rhino under the icy water. Mysterio and Kraven showed up next, using illusions of Doctor Octopus and Shocker to put Spidey off-guard.
Kraven and Mysterio chased Spidey into a department store, and Spidey knocked out Kraven's animal-like senses by smashing a perfume bottle on his face. Mysterio then unleashed his robotic Homunculis, which Spider-man quickly destroyed. After Spidey followed a robot Mysterio up to the second floor, Kraven unwittingly gave away the trap, and the robot exploded. Spider-Man rescued a nearby mall Santa Claus and elf as Kraven was knocked out by the explosion and webbed up. Upon trapping Mysterio and making sure he was really Beck, Spider-Man asked him who the Master Planner is, but Beck refused. Only Mysterio taken into custody, however, as Tinkerer had managed to extract the other members at the last minute. ("Reinforcement")