Spider-Man changed in the 1990s in some drastic ways. The artwork of Todd McFarlane helped change the tone and feel of the comics and also introduced Spidey's popular new villain, Venom. Spider-Man then hit the middle of the decade, where he experienced his most critically derided storyline, the Clone Saga.

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While the decade started off exciting with the new look and villains, things ended up in a rough spot. After the Clone Saga, Marvel went through one of its darkest periods creatively and Spider-Man didn't fare any better than other comics from that era. However, before the fall came some great comic book issues for the Wall-Crawler.

Amazing Spider-Man #337 (August 1990)

The Sinister Six vs Spider-Man in #337.

In 1990, it was time to bring The Sinister Six back to prominence. This supervillain team was the first that saw Spider-Man's core villains team up to battle him, making their first appearance in Amazing Spider-Man Annual #1.

In Amazing Spider-Man #337, the Sinister Six was back and they set their sights on Spider-Man again, this time with Doctor Octopus at the lead. This book remains important because it made the Sinister Six important again in the pages of Spider-Man and it also helped further one of Spidey's best romantic storylines — Flash Thompson and Black Cat.

Amazing Spider-Man #347 (May 1991)

Venom holding Spider-Man's skull.

At the end of the 1980s, Spider-Man met Venom in one of his best issues. Venom, who was only a villain because he hated Spider-Man, wanted nothing more than to kill Spider-Man and then just move on with his existence. Eddie Brock, who hated Peter Parker, was more than willing to oblige.

In Amazing Spider-Man #347 by David Michelinie and Erik Larsen, Spider-Man realized he needed to end this feud. This issue was very important as it had Spider-Man fake his own death to appease Venom, knowing that the alien and Eddie Brock could finally move on in peace. This played into their future relationship as well, when Venom stopped his relentless pursuit of Spider-Man.

Spectacular Spider-Man Vol. 1 #180 (September 1991)

Spider-Man vs Green Goblin on #180.

Harry Osborn was Green Goblin when the 1990s began, taking the role from his father and seeking revenge against Spider-Man for the belief that the Wall-Crawler killed his father. In Spectacular Spider-Man #180, the two fought in one of their greatest battles.

In this issue, Harry was going deeper into his delusions, looking at old pictures of his father and Peter Parker, wanting nothing but revenge. This issue shows Harry slowly losing his mind and finally having the breakdown and becoming Green Goblin again, starting his war with his old friend anew.

Amazing Spider-Man #361 (February 1992)

Carnage battles Spider-Man in 361.

In 1992, Amazing Spider-Man #361 by David Michelinie and Mark Bagley introduced the world to Spider-Man's newest villain, Carnage. A serial killer named Cletus Kasady, Carnage was the offspring of Venom and attached to the man in prison.

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The first time that Spider-Man and Carnage battled was in this issue, and it presented a new villain that pushed Spidey to the limit. Carnage was stronger than Venom and Spider-Man, so the two hated rivals had to team up to eventually beat him. After this issue, Carnage became one of Spider-Man's deadliest enemies.

Spectacular Spider-Man Vol. 1 #188 (May 1992)

Spider-Man fighting Vulture.

Spectacular Spider-Man #188 had Spider-Man in the last part of a multi-issue battle with The Vulture. This battle saw Vulture attacking Spider-Man and trying to kill him once and for all. The twist here is that Vulture learned he was dying of cancer and that is what set him off on this vendetta.

The book remains a great issue from the 1990s because Spider-Man battled one of his oldest foes and realized that his enemy was dying, and there was nothing they could do about it. In the end, Spider-Man finally beat Vulture and forced him to apologize for what he did to Aunt May earlier in the issue. The moment May told Vulture forgiveness is between him and God, it was a huge moment in the life of the supervillain.

Spectacular Spider-Man Vol. 1 #200 (May 1993)

Spider-Man fighting Green Goblin on #200.

In Spectacular Spider-Man #188, Harry Osborn submerged himself in the Goblin serum and turned into Spider-Man's most dangerous supervillain again. This time, he had a lot to lose as he had a wife and a young son. That made Spectacular Spider-Man #200 - one year later - such a remarkable issue.

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In this book, Harry decided to kill Spider-Man and himself in the process. However, Mary Jane and Harry's own son were in the building that was set to explode and he ended up saving both of them before going back in and saving Spider-Man as well. The issue ended with him dying, one of the most important moments in the relationship of Peter Parker and Harry Osborn.

Spider-Man Unlimited #3 (November 1993)

Doctor Octopus looking at Spider-Man.

From the start of his comic book existence, Spider-Man's greatest rival was always Doctor Octopus. The villain pushed Spidey to the limit time and time again and was always the one man who made Peter Parker's life hell, both with his brains and his evil schemes and plans.

In Spider-Man Unlimited #3 by Tom DeFalco and Ron Lim, the origin story of Doctor Octopus played out. This took him from childhood to his adult years and showed how and why he became such a ruthless villain. For Spider-Man fans, this issue is a must-read to get into the mind of Otto Octavius.

Amazing Spider-Man #400 (April 1995)

Spider-Man on a tombstone on 400.

In 1995, Spider-Man was involved in the Clone Saga, paying off a storyline that began in one of the best Spider-Man comics of the 1970s. While that original Clone Saga was well done, fans mostly rejected the Clone Saga in the 1990s. Despite that, one of the best comic issues of the decade came during that event.

In Amazing Spider-Man #400 by J.M. DeMatteis and Mark Bagley, Aunt May died. This was a heartbreaking issue that included May telling Peter that she knew about his secret identity all along. However, what made it great was the death of Aunt May herself, a moment that had all Spider-Man fans fighting back tears.

Untold Tales Of Spider-Man Annual 1996 (December 1996)

Classic Spider-Man swinging through the city.

In the middle of the Clone Saga, Marvel tasked its creative team in showing untold stories of Peter Parker, Ben Reilly, and Spider-Man. While most of that era was forgettable, there was a good issue that hit called Untold Tales of Spider-Man Annual 1996 by Kurt Busiek and Mike Allred.

This went back in time and told the stories in between issues of the classic Stan Lee and Steve Ditko issues from the 1960s and featured an animated style homaging Ditko. This remains one of the 1990s best Spider-Man comics thanks to its tone, which featured a fun story with the Fantastic Four. It was a fun throwback story in an era where things got a little too serious for a few years.

Webspinners Tales of Spider-Man #1 (November 1998)

Mysterio fighting Spider-Man.

In 1987, J.M .DeMatteis took the minor character of Kraven and reinvented him with the story Kraven's Last Hunt. In 1998, 11 years after that groundbreaking series, DeMatteis tried to recreate the magic with another villain, this time with Mysterio.

In Webspinners Tales of Spider-Man #1, Quentin Beck was back as Mysterio and featured an untold story of Spider-Man from the 1960s with the villain trying to go straight, but failing to find a real job thanks to his past. This first issue is a great one, with Mysterio's origin playing out, showing why he ended up as one of Spider-Man's most persistent villains.

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