It's become fashionable in geek circles to bash Raimi's Spidey films because 3 was something of a letdown (personally I thought that, flaws aside, that last film was still more good than bad) but Raimi deserves enormous credit for bringing the web-slinger to the screen over the course of three films with as much faithfulness to the source material as he did. I'm sure at many points in the development process on that first trip to the screen, it was even in question as to whether the classic red and blue costume would make the journey to live-action and for that, and many other choices that Raimi likely fought hard for, he deserves a huge thanks.
Sure, Raimi's Spidey trilogy wasn't perfect but no one vision of Spider-Man on film is going to completely jibe with each fan's perception of what the ideal adaptation should be. The organic web-shooters was a touch I thought was inspired (credit for that goes to James Cameron's original scriptment) and the heavy emphasis on Peter Parker's emotional life, rather than gunning for all-out action, was true to the soap opera elements of the comic. Villain-wise, Raimi broke even with Doc Ock and Sandman being outstanding (even if Sandman could've used more screen time), Venom being dismal, and The Green Goblin overcoming a goofy outfit (to be fair, the Power Rangers upgrade Raimi went with isn't any goofier than the GG of the comics - I mean, honestly, the guy carries a purse and has purple booties!) thanks to the inspired scenery chewing of William Dafoe. And while some can quibble with the casting choice of Maguire or Kristen Dunst (my own casting issue was with Bill Nunn's Robbie Robertson - a good actor but too paunchy to resemble the classic Robbie from the comics), no one can say that J.K. Simmons wasn't THE perfect J. Jonah Jameson. Like Judi Densch's M in the Bond films, I believe that Simmons' JJJ should be the one cast member to make the transition over to the reboot.
As for the reboot itself, I'm all for it. Spider-Man 4 or no, Maguire is getting too long in the tooth to play the perennially youthful Spidey. And while the resetting of the Spidey movie-verse back to high school has some fans crying, and even believing that Sony is cynically chasing the Twilight crowd, I don't get the uproar - classic Spidey is a high school character. Why not bring him back to high school if you're going to reset the series? I do agree with the general consensus that a retelling of the origin story should be bypassed - this reboot needs to hit the ground running rather than backpedal.
It's too early on in the process to comment on Sony's plans because so little information has been released but my hope is that the new film will place on emphasis on fun, that it'll buck the darkening trend of the comic adaptation landscape (fine for a character like Batman but a bad fit for Spidey), and that Peter Parker will break into tears much less. I'm all for Peter showing some emotions but Raimi turned the character into a sobbing wreck a few times too many for my taste. In terms of villains, I expect they'll be going after a new version of either Green Goblin or Doc Ock (pumpkin bombs and mechanical tentacles would both look sick in 3-D, by the way). Even though they've both been done so recently, I think it's hard to kick off a Spidey series without using one of the character's two main villains. There's plenty of classic Spidey villains that have yet to make the jump to the big screen but foes like Scorpion, The Rhino or Mysterio seem like sequel material to me. Oh, and how about calling the new movie The Amazing Spider-Man? That'd be cool.
Finally, with all the activity on the Spider-Man front, what I really want to know is why hasn't anybody released the classic '80s cartoon Spider-Man And His Amazing Friends or the '70s live-action Spider-Man TV show on DVD yet? I mean, come on - both these series introduced generations of kids to Spidey and encourged them to follow his exploits in the comics. Even though they have some serious, serious cheese issues, you'd think it'd be a natural to release them. Every time a new Spider-Man film came out, I kept expecting to hear a DVD announcement on one or both of these properties but maybe the reboot will finally be the right occasion. Or maybe they're tangled in a legal web so great that even Spidey - and his lawyers - can't undo it.