First came the Spider-Man series starring Tobey Maguire.
Now he's played by Andrew Garfield (in The Amazing Spider-Man).
Why didn't they just make a new generation, such as the first Spider-Man's son?
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The reason for the different actors is because it is a different universe. The two movie series are based on two separate Spiderman story lines. In which the characters are very different including the different love interest, Mary Jane for Spiderman's original universe and Gwen Stacy in the Amazing Spiderman. The characters sometimes overlap but they do not interact in the same way in the different universes.
My guess is that it's basically a matter of focus testing and wanting to stick to what the average film goer is familiar with.
The general population knows that historically speaking, Peter Parker is Spider-Man. This fact changes in the comics, but the average man-on-the-street - if they know Spider-Man's identity will likely say Peter.
When The Amazing Spider-Man was released, many viewers (like my mother) who didn't follow the production or the trailers closely, went in not understanding that the film was a reboot of the franchise, despite it not being hidden or denied by the studio at all. They just assumed that it was a new Spider-Man and that it must be a continuation of the Raimi/Maguire movies.
To begin a new franchise - with the same titular character and a different identity would only confuse the average viewer.
Studios also run the risk of confusing or upsetting fans or people vaguely familiar with the characters.
Take the examples of Kingpin, Nick Fury or even Perry White. Historically, all three are white males in the comics. Many fans were outraged that Michael Clarke Duncan was chosen to play Kingpin, or that Lawrence Fishburne was chosen to play Perry White. There was even confusion as to just why Nick Fury was being played by Samuel L Jackson - even though the Ultimate version of Nick Fury was based on him.
In the end, while literally taking a character to a whole new generation, it can be more trouble than its worth financially - and that's all the studios care about.
The reason there are different characters playing Spider-man because they are completely different imaginings of it.
Think about this, in Toby's Spiderman series Spider-man was able to shoot web from his palms. Now in the comic books he never had this ability until I believe it was well into the comic book series.
The new series is a remake of the Spiderman franchise trying to follow in a closer path to the comic book, hence why Andrew creates the webshooters like in the comic book.
Anytime you see a movie about a Superhero or comic in general and they change actors it's most likely because they are doing a complete and separate story than the previous one.
Same thing happened with The Hulk and The Incredible Hulk, two completely different imaginings of the Hulk with different actors.
So the real reason for all the different Spider-Man's is this: when Spiderman first kicked off it was under marvel and did exceptionally well. (But believe or not marvel wasn't at the top of their game like they are today....so they sold rights to Sony...with that being said...they had to use different actors and change to storyline up... Hence the change from Spider-Man being in love with Gwen instead of Mary Jane. When Sony didn't do so well after the amazing Spider-Man 2 Marvel had started the avengers and had a way to incorporate Spider-Man and make more money off him. So Sony jumped on the wagon. That being said they once again had to change actors.