Spider-Man 2 (2004) is the most timeless Spider-Man film.

Cyrogenic

Giancarlo Stanton
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Out of all the Spider-Man movies made so far, Spider-Man 2 seems to be the least dated and most timeless and I think it will stay way for many years to come.

The whole TRL/millennial vibe of Spider-Man, as well as the obvious post-9/11 atmosphere of New York that this movie takes place will definitely date the film as more and more years go by. And Willem Dafoe's Nickeldoeon version of the Green Goblin will be viewed the same way people view Jack Nicholson's Joker now. Macy Gray singing in the New York Parade, as well as the *beep* Nickelback song on the Spider-Man soundtrack will clearly set this film as a product of the Early 2000's.

While Spider-Man 3 has the best action and special effects of the series, the story hasn't really aged well at all and the flaws of the film have gotten bigger and bigger since the film came out in 2007. It's only going to get worse and worse as more time passes by. Many years from now, Spider-Man fans are going to look back on Tobey Maguire strutting down the streets of New York with an emo haircut the same way Batman fans look back on the Bat-Nipples and Bat-Credit-Card in Batman & Robin and shudder.

In regards to Marc Webb's Amazing Spider-Man series, I think once the newness of his films ware off and they are no longer recent, the love for these films will disappear completely and they will be looked at for they really are. The Christopher Nolan-influenced tone of The Amazing Spider-Man, as well as the attempt to cash in on The Avengers with The Amazing Spider-Man 2 will definitely set these films as a product of the Early 2010's. The Twilight-vibe of the romance in these films, as well as Andrew Garfield's hipster/skater boy-esque take on Peter Parker/Spider-Man isn't going to age well with people at all. 20 years from now, Andrew Garfield's portrayal will be to Tobey Maguire's portrayal of the character like how Val Kilmer's portrayal of Batman is to Micheal Keaton's portrayal of the character is now.

While Spider-Man 2 doesn't feel like a product of it's time and feels like it could belong to any decade. Even 10 years later, the story still holds up incredibly well and the film hasn't aged a bit. I still consider it to be one of the best superhero movies of all time. It is still the high mark of the Spider-Man series, and will continue to be set as the standard in which all future Spider-Man films are compared to.
 
While Spider-Man 3 has the best action and special effects of the series, the story hasn't really aged well at all and the flaws of the film have gotten bigger and bigger since the film came out in 2007. It's only going to get worse and worse as more time passes by.
No, they haven't. No, it won't.
Many years from now, Spider-Man fans are going to look back on Tobey Maguire strutting down the streets of New York with an emo haircut the same way Batman fans look back on the Bat-Nipples and Bat-Credit-Card in Batman & Robin and shudder.
With glee?
 
I just rewatched it for the first time since before The Amazing Spider-Man came out. I have always said it is among my favorite comic book movies (right up there with The Dark Knight, Batman Begins, etc.). But it really is a timeless movie.

Yes, the CGI has dated quite a bit. And nobody has a smartphone. Heck, they still use pay phones in this movie. Nonetheless it just all works. It is such a full, complete and totally satisfying cinematic superhero experience. It might miss details about the Spidey mythos--Peter not having a sense of humor, MJ being an introvert--but it captures effortlessly that feel of everyday "New York Minute" anxiety and humor. The world feels lived in and larger than life comic booky at the same time. But it still feels lived in, unlike the glossy sheen of the Marc Webb movies or even the even more cartoonish (if "serious") flatness of the MCU films.

But more important than any of that is it just a visceral experience. You go on a major journey with Peter Parker and despite it being really about his personal struggles with MJ and Doc Ock it feels like an epic and complete cinematic adventure. It's not an episode of a TV show like most superhero movies today.

It might not have it in its moniker, but this really is the amazing one.
 
And nobody has a smartphone. Heck, they still use pay phones in this movie.

It all works with the quasi 60's aesthetic Raimi was going for.
 
You know, of all the three films, visuals in this film are the best looking, hardly look outdated.
Effects in Spider-Man 3 are supposed to be better, but they look outdated.
 

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