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Following his first appearance in Amazing Fantasy #15 in late 1962, Spider-Man began his first ongoing series in early 1963. Title ran for 35 years, ending in 1998 as part of a soft-reboot by John Byrne. This reboot began with a 12-issue Spider-Man: Chapter One miniseries, followed by Amazing Spider-Man (2nd series). This second series resumed "legacy" numbering after #58. Spider-Man (4th series) also resumed legacy numbering after its #32.
Series had 31 to 39 annuals, depending on how one might count. There were originally 28 numbered annuals, running from 1964 to 1994. Annual was replaced in 1995 by a "Super Special." In 1996 annuals resumed but were numbered by the year in which they appeared ('96, '97, 1998, 1999, 2000 & 2001. The latter three annuals (1999 to 2001) are more accuratelty associated with Amazing Spider-Man (2nd series), though they are technically the same Amazing Spider-Man Annual (1st series).
Amazing Spider-Man (2nd series) resumed 1st series "legacy" numbering after #58 in 2003. In 2008, it resumed annuals and utilized legacy numbering. A total of 5 annuals between 2008 & 2012 were published th numbering #35-39. In 2014, Amazing Spider-Man (3rd series) was launched and in 2015 it had its own Annual #1, making that Amazing Spider-Man Annual (2nd series) #1. Subsequent Amazing Spider-Man annuals utilized #1s, complicating numbering schemes.
#1 - first Chameleon, J. Jonah Jameson#2 - first Vulture#3 - first Doctor Octopus#4 - first Sandman, Betty Brant#6 - first Lizard#9 - first Electro#10 - first Enforcers#13 - first Mysterio#14 - first Green Goblin (Normal OSborn)#15 - first Kraven the Hunter#20 - first Scorpion#25 - first Spider-Slayers, Spencer Smythe, Mary Jane Watson (partial)#28 - first Molten Man#31 - first Gwen Stacy#36 - first Looter#38 - last Steve Ditko issue#39-40 - Osborn unmasked as Goblin#41 - first Rhino#42 - first full Mary Jane Watson#46 - first Shocker#48 first Vulture II (Blackie Drago)#56 - first Captain Stacy#78 - first Prowler#81 - first Kangaroo#90 - death of Captain Stacy#113 - first Hammerhead#121 - death of Gwen Stacy#122 - death of Green Goblin (Norman Osborn)#129 - first Punisher#134 - first Tarantula#139 - first Grizzly#143 - first Cyclone I#144 - Gwen Stacy clone#146 - first Jackal#149 - first clone saga ends#167 - first Will o' the Wisp#172 - first Rocket Racer#176 - first Green Goblin II (Bart Hamilton)#180 - death of Green Goblin II#185 - Peter Parker graduates college#194 - first Black Cat#210 - first Madame Web I#212 - first Hydro-Man#222 - first Speed Demon#229-230 - vs. Juggernaut#238-239 - first Hobgoblin#252 - first black costume#253 - first Rose#255 - first Black Fox#256-257 - first Puma#257 - secret of Symbiote revealed#263 - first Spider-Kid#272 - first Slyde#280-281 - first Sinister Syndicate#282 - X-Factor crossover#298 - first Todd McFarlane#299 - first full Venom#344 - first Cardiac#361 - first Carnage#365 - 30th anniversary
Crossovers/Events/Major Stories:
#248 - the Kid Who Collected Spider-Man#268, 273-274 - Secret Wars II#279 - Missing in Action#284-288 - Gang War#290-292 - Peter proposes to Mary Jane#293-294 - Kraven's Last Hunt (parts 2 & 5)#311-313 - Inferno#320-325 - Assassin Nation Plot#326-329 - Acts of Vengeance#334-#339 - Return of the Sinister Six#341-343 - Powerless#353-358 - Round Robin: the Sidekick's Revenge#361-363 - Carage#378-380 - Maximum Carnage (parts 3, 7 & 11)#390-393 - Shrieking#403 - Trial of Peter Parker pt 2#404 - Maximum Clonage pt 3#405 - Exiled pt 2#406 - Greatest Responsibility pt 1#408 - Media Blizzard pt 2#409 - Return of Kaine pt 3#410 - Web of Carnage pt 2#411-412 - Blood Brothers pt 2 & 6#415 - Onslaught#418 - Revelations pt 3#440 - Gathering of Five pt 2#441 - Final Chapter pt 1 (last issue)