The Sinister Six are a group of supervillains appearing in American comic books published by Marvel Comics, mainly those featuring Spider-Man. The members are drawn from the character's list of enemies, with the original members forming the team in The Amazing Spider-Man Annual #1 (October 1964). Led by Doctor Octopus (introduced in issue number 3), the team in its premiere followed swiftly the very early appearances of many of the most enduring members of Spider-Man's rogue's gallery: Vulture (the title's first super-villain, in issue #2), Sandman (issue #4), Electro (#9), Mysterio (from #13), and Kraven the Hunter (#15). While Doctor Octopus has generally remained its leader, the Sinister Six has had multiple variations of composition. The team has been adapted into various forms of media, mainly in animated series and video games. A film based on the team is in development as part of Sony's Spider-Man Universe. Publication history The Sinister Six first appeared in The Amazing Spider-Man Annual #1 (January 1964). Fictional team biography Original Sinister Six After suffering two defeats from Spider-Man, Doctor Octopus is separated from his tentacle pack. After his tentacle pack breaks free and helps Doctor Octopus get out of prison, he contacts every known supervillain who had crossed paths with Spider-Man. Only Electro, Kraven the Hunter, the original Mysterio, the Sandman, and the original Vulture respond. As none of the members are willing to relinquish the honor of killing Spider-Man themselves, they decide to challenge Spider-Man individually with the order in which they face him determined by a random drawing. The Sinister Six kidnap Aunt May and Daily Bugle secretary Betty Brant, holding them hostage in order to force Spider-Man to confront them. Spider-Man defeats the Sinister Six members one-by-one, mocking their decision to battle him individually instead of as a team in front of Doctor Octopus, the last one to be defeated. "The Return of the Sinister Six" In The Amazing Spider-Man #334–339, Doctor Octopus recruits Electro, Sandman, Mysterio, and Vulture, along with the demonic Hobgoblin (since Kraven the Hunter had recently died), as part of his plan to take over the world. However, this was a trick, part of a larger plan by which Doc Ock alone would be the master of the world, by releasing a chemical into the atmosphere that would cause pain in anyone who attempted to use cocaine; he would then sell his cure for the chemical to