First Appearance of Sinister Six: Spider-Man Annual #1

The Sinister Six first appeared in The Amazing Spider-Man Annual #1, cover-dated October 1964, by Stan Lee and Steve Ditko (Wikipedia). PriceCharting describes it as a 72-page annual. The original six were Doctor Octopus, Electro, Kraven the Hunter, Mysterio, Sandman and the Vulture; the annual is the team's first appearance, not the first appearance of each villain; Sandman, for example, had debuted a year earlier in The Amazing Spider-Man #4.

PriceCharting values for The Amazing Spider-Man Annual #1 (1964), retrieved September 25, 2026:

• Ungraded: $215.36 (about two sales a week)
• CGC 4.0: $797.61
• CGC 6.0: $1,554.65
• CGC 8.0: $3,751.72 (about two sales a year)
• CGC 9.2: $20,740.00 (about one sale a year)
• CGC 9.8: $44,944.19 (about one sale a year)

PriceCharting notes that white pages sell for more than off-white pages in high grade.

From Wikipedia's history of the team:

• Original (1964): Doctor Octopus, Electro, Kraven the Hunter, Mysterio, Sandman, Vulture.
• The Return of the Sinister Six (The Amazing Spider-Man #334 to #339, 1990): Doctor Octopus leads Electro, Sandman, Mysterio, the Vulture and the Hobgoblin, who replaces the dead Kraven.
• Sandman's lineup: Venom temporarily replaces Doctor Octopus, alongside Electro, the second Kraven the Hunter and the Vulture.
• Superior Six: Otto Octavius, in Peter Parker's body as the Superior Spider-Man, captures former members Sandman, Electro, Chameleon, Mysterio and the Vulture and forms his own team.

Sony planned a Sinister Six spin-off film. Wikipedia says it was postponed and then canceled after Sony and Marvel Studios announced their 2015 deal to share Spider-Man.

Photograph the front cover straight on, then the indicia (the small print on the first page or inside cover with the title, issue number and date). ComicLens reads the title, issue number and cover from the photo, matches the likely issue with a confidence indicator you can correct by hand, and shows a reference price range that moves with the grade you pick. The annual is often confused with later annuals and reprints that reuse the story; check that the indicia says Annual #1 and 1964. There are free scans every day; the range is a reference estimate, not an appraisal or an offer.

Research and drafting were assisted by AI and checked line by line against the sources listed on this page. Prices are the figures shown by the named source on the date given; they change with the market, and a grade that trades about once a year can move a lot on a single sale.