The first "Sinister Six' group was organized by 'Doctor Octopus', debuting in Marvel Comics' "The Amazing Spider-Man Annual" #1 (January 1964).
"...'Doctor Octopus' contacts every known enemy of 'Spider-Man', but only 'Vulture', 'Electro', 'Kraven the Hunter', 'Mysterio' and 'Sandman' respond.
"Knowing he'd never be able to keep the team together, Doc Ock formulates a battle plan ...
"...in which each individual member of the 'Sinister Six' would battle Spider-Man in a carefully chosen location.
"Spider-Man himself had his own problems, as he had somehow lost his powers and prepared to return to normal life as a teenager.
"As Peter returned to his normal life as a student and a freelance photographer, he was unaware of the fact the Sinister Six kidnapped 'Daily Bugle' secretary 'Betty Brant' and Peter's 'Aunt May'.
"'The Vulture tells 'J. Jonah Jameson' that Betty was being held hostage along with Aunt May and if he wanted to see them alive, Spider-Man would have to battle the Sinister Six..."
Click the images to enlarge and Sneak Peek "The Sinister Six"...