1. Marvel Masterworks: The Amazing Spider-Man
When it comes to Spider-Man, it's really hard to beat the source material. Stan Lee and Steve Ditko delivered to comic book fans a hero that they could truly relate with. Peter Parker looked like your average comic fan, had every day concerns, and had one hell of a sense of humor. Stan Lee delivers some of his best characterizations in this series and Steve Ditko's art is nothing short of innovative. Writers can't stop ripping off the Spider-Man formula.
2. The Night Gwen Stacy Died
This is really a no-brainer. Possibly Spider-Man's greatest failure as a superhero. The story really stands as a challenge to the superhero stereotype as it was built in the Silver Age. Heroes were never too late and never failed at saving a life especially the life of a loved one. Spider-Man can't even believe it himself when he pulls Gwen up only to find her dead. This issue was a milestone that lead superhero comics into a murkier age.
3. Spider-Man: House of M
I think I really love this story because it defies the normal conventions of a Spider-Man story. Instead of struggling in the mire, Peter Parker's life is great in the alternate reality of House of M. He's wealthy, famous, and generally loved by all. Gwen is still alive, they're married, and they have a son. Of course, reality catches up with Pete and his life falls apart in traditional Parker fashion. The part that really clinches it for me comes at the end. Most Spider-Man stories are about guilt. They are about the words "With Great Power Comes Great Responsibility" and Peter's ability to live up to them. Uncle Ben, the man who originally said these words, tells Peter in this story: "I'm ashamed because I never said it to anyone else." The world's not on your shoulders. Beautiful.
4. Kraven's Last Hunt
This is a frightening one. It begins with Spider-Man getting shot point blank in the chest by Kraven and buried in some unmarked grave. For a while you don't even know if he's still alive. Meanwhile, there's a cannibal in the sewers of New York and Kraven's having a mental breakdown. Quite the thriller delivered to you by one of my personal favorite Marvel creative teams: J.M. DeMatteis and Mike Zeck.
5. Spider-Man: Fever
This is a WEIRD one. To celebrate the historic collaboration between Stan Lee and Steve Ditko, Brendan McCarthy writes a surreal tale starring their two greatest creations: Spider-Man and Doctor Strange. Weaving an Aleister Crowley-esque legend into Marvel's occult history, McCarthy brings a fresh take on magic into continuity. Spider-Man gets pulled through the ringer by a group of spider-demons who throw doubt onto his origin. The art is weird and beautiful. It stands as a unique Spider-Man epic.
6. Ultimate Spider-Man
Say what you like about Brian Michael Bendis, but he really delivered with Ultimate Spider-Man. Bendis reminds everyone why Spider-Man is such a great character by taking him back to his roots only in a modern setting. Great dialog, compelling characterizations, and the art of Mark Bagley really brought the world of Spider-Man to life for a new generation. Sure, it eventually got to be too big and too much, but the early story-arcs of Ultimate Spider-Man are worth the read.
7. The Death of Jean DeWolff
Peter David owns. Case in point. In the Death of Jean DeWolf, David spins a brooding tale of murder and revenge. Spider-Man comes face to face with the issue of the death penalty as he contemplates ending the life of a merciless serial killer who's taken the life of a friend. Spider-Man gets grim and gritty in a good way here with the wonderfully somber art of Rich Buckler
8. No One Dies Part One of Two: Awakening
I have to give Dan Slott some love on this one. The funeral of Marla Jameson sends Spidey into an existential nightmare where he confronts just about every character that has ever died during his comic's publication. My personal favorite moment was the Scourge scene where the murderous vigilante explains to Peter that after he's done killing all of the c-list villains then there won't be any need for Spider-Man's nightly patrols. That nice little meta-joke explains exactly why the Marvel editorial staff set Scourge loose in the first place to shake up Marvel in the mid-80's. Marcos Martin's artwork is nearly perfect, as well. This issue is a real highlight of Slott's run.
9. Maximum Carnage
This is the story that got me hooked on Spider-Man as a kid. It truly is a blockbuster. Carnage goes on a rampage throughout New York City leading a team of the most terrifying Spider-Man villains conceived in the Modern Age. Spidey has to team-up with lesser-known heroes and even his arch-enemy Venom to end the madness. I still get chills when Captain America makes his surprise entrance to bring in the cavalry. Utilizes the talents of many great Spider-Man creators including J.M. DeMatteis, Tom Defalco, and Mark Bagley.
10. What if Spider-Man joined the Fantastic Four?
Don't overlook this issue just because it isn't in continuity. This story is a very unique approach to the comic narrative. Instead of making up a completely new adventure, Roy Thomas goes back to the exact stories that made up the early days of both Spider-Man and the Fantastic Four and rewrites them. The only difference is Spidey is now a member of the team. Some might argue that this is only a fan exercise and not a good example of original writing. I would argue that Thomas was exploring the limits of shared-universe continuity. This wasn't just another story to him. He was rewriting history.