Personal preference, not binding, blah blah, etc.
1. Stan Lee - It's true that when you go back to read some of Lee's early stuff, it can be a bit hokey and overly bombastic, but for me, his Spider-Man stuff holds up better than anything else, even better than Fantastic Four. Maybe that's because Lee and Ditko co-writing had a nice push-pull like you get with a good writer/editor relationship, or maybe it's any of a hundred other possible reasons, but at any rate, the early Spider-Man issues are some of my favorite Silver Age Marvel books.
Spidey's rogues gallery is one of the best in comics, and most of them were introduced during Lee's run. Green Goblin, Scorpion, Kraven, Doctor Octopus, Electro, The Lizard, Mysterio, Rhino, Shocker, Kingpin, The Sandman... a cornucopia of bad guys who remain in use today. Then there are villains who didn't endure, but who were memorable in their time, like Lee's epic about the magic tablet and "The Big Man," and the supporting cast that was established, from Mary Jane to Flash Thompson, Robbie Robertson, Gwen Stacy and of course J. Jonah Jameson, one of the best, love to hate 'em nemesis characters of all time.
In fact, Lee was #2 on this list until I realized just how much of a great foundation he laid for all that came later, and much as I love Stern's take on Spider-Man, it owes a lot to the groundwork from Lee's run.
2. Roger Stern - Stern wrote the perfect Spider-Man for me. Heroic, funny, neurotic, dangerous as hell when his righteous anger got kicked in. He also created one of the best villains of all time, the Hobgoblin, although of course points must be deducted for the lame ending when Stern left the book, and a few more for when he came back a few years later and did a miniseries that further confused the issue and had me thinking "Wait, who was that guy again?"
Stern also wrote "The Kid That Collected Spider-Man" and "Nothing Can Stop The Juggernaut," two of the best Spider-Man stories ever put to paper, and started the maturation of Mary Jane to the point where she became a viable long-term partner for Peter Parker.
3. Gerry Conway - I've never been a huge Conway fan, but when I read his Amazing Spider-Man, I realized how good he could be. If nothing else, the guy gave us the original clone story (which was great, as compared to the '90s clone saga) and the Death of Gwen Stacy, but he also introduced the Punisher and made Harry Osborn the Green Goblin, a notable and important development in that character's history. There were also any number of fun, memorable one-shot stories throughout his run.
4. Peter David - Though he didn't write that many Spider-Man stories due to office politics, Peter David's brief tenure on Spectacular, and his work on Web of Spider-Man, was memorable. The Sin-Eater storyline and all the work he did on Jean DeWolff was probably the best thing to happen to Spidey's police interaction since Captain Stacy, and David's sense of humor, always a prominent aspect of his writing, was a perfect fit for Spider-Man.
In fairness, because his tenure was relatively short, David was able to avoid any handicaps that would move him further down the rank, unlike a few of my honorable mentions (below).
5. Brian Michael Bendis - I know, those of you who know I'm not a huge Bendis fan these days are surprised. But Bendis did the impossible, along with Mark Bagley, and made Ultimate Spider-Man not a terrible idea but a fantastic, modern reinvention of the character. He captured the neuroses and the humor of Spider-Man better than anyone since Stern, he expanded and filled out the character's origin and development as a hero, and while things started to go off the rails after a while, those first 30 or so issues of Ultimate Spider-Man are still some of the best stuff to hand a new reader who wants to try the character out.
In addition, Miles Morales is showing a lot of the same spark of originality that the early Ultimate Spider-Man issues had, and if the character does endure (which I hope he will), Bendis will be responsible for creating what is essentially another viable Spider-Man, more popular and more easily accepted than the only other character folks might accept as Spider-Man, Ben Reilly.
I'd love to credit Tom DeFalco, whose follow-up to Roger Stern's run was actually pretty true to the tone, especially at first, but his later work on the Clone Saga sort of disqualifies him.
Ditto J. Michael Straczynski, who started off relatively strong, hit on some really nice ideas (Peter as teacher, Aunt May figuring out the secret), but had some not so great ones and of course, bears some of the blame for the terrible One More Day story.
David Michelinie is a writer I've always been fond of, and like him or hate him, you have to admit that Michelinie co-creation Venom is a memorable Spider-foe. He also did great stuff with Silver Sable and Paladin, two characters I really like. But he was working in the '90s, and was drawn into all the terrible storytelling conventions that implies, so at least half his run is pretty weak.
J.M. DeMatteis needs to be mentioned for "Death of Kraven," and indeed some of his '90s and '00s work was pretty solid, but a lot of his Spidey stuff is unremarkable.
Mark Waid is fantastic at Spidey (Check out Amazing Spider-Man #677) but hasn't written quite enough of the character to be an all-time favorite. I'd sure love to see more from him, though.
Dan Slott can be fantastic on Spidey (see Spider-Man/Human Torch) but he's been shackled by the Brand New Day status quo, and seems to just now be fighting his way out of it. If he had his own continuity to work with rather than the one Quesada and company saddled him with, I'm sure he'd be on this list, and I still think he might wind up there.
Next time: Least Favorite 5 Spider-Man writers. Then I might tackle Favorite artists.