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Dyeing for Your Art: Dunst (it was a wig in the first film, but she liked the look so the sequels are literal cases); Maguire, Church, and Grace all gained double-digits pounds of muscle.
Interesting considering Dunst is a blonde playing a redhead, and Bryce Dallas Howard is a redhead playing a blonde.
Executive Meddling: Spider-Man 3: The reason Venom and Gwen are in it (though Eddie Brock was always planned, just not his alter-ego).
Fake American: Rosemary Harris, who plays Aunt May, is British.
Spider-Man 2: Alfred Molina, who plays Doctor Octopus, is from London. When he says the line, "I should've known Osborn wouldn't have the spine to finish you!", his voice slips a bit.
Daniel Gillies, who plays John Jameson, is Canadian and grew up in New Zealand.
It's a good thing that Peter never had his head cut off in the middle of the desert by drug crazed journalists, otherwise he'd never be able to stop Special Agent Smecker from killing Claudia, who apparently finally grew up.
Joel McHale as the bank teller, and Donnell Rawlings (Ashy Larry) as the witness of the pizza "heist" (the source of this film's Memetic Mutation, by the way). Apparently, Dave Chappelle himself was supposed to be the guy in the elevator, but for whatever reason he was replaced by Hal Sparks of Queer as Folk/Best Week Ever fame.
Joel would reference his cameo three years later in an episode of The Soup with a spoof trailer of Spider-Man 3, where his bank-teller character becomes a Magnificent Bastard.
What Could Have Been: Alicia Witt, Tara Reid, and Eliza Dushku all auditioned for the role of Mary Jane. Kate Hudson was the initial choice but she turned down the role.
Jake Gyllenhaal would've taken over the role of Peter Parker if Maguire's back problems became too much.
Which makes a lot of sense; they resemble each other so much, they actually played brothers in the film of the same name.
The script for the fourth film which caused Raimi to leave. According to reports, it had Peter married to Mary Jane for several years, Adrian Toomes replacing Jameson as head of the Daily Bugle, Spider-Man deliberately killing the Vulture, inciting the wrath of Felicia Hardy -who would here not be the Black Cat, but the Vulture's daughter, with whom Peter would essentially cheat on Mary Jane with; and most notably, the ending would have had Mary Jane leaving with her and Peter's baby, and "Spider-Man No More" happening again.
Sam Raimi also wanted Dr. Curt Connors (who was played by Dylan Baker in the previous two films) to become The Lizard at some point in the film, and the very last scene of the movie was rumored to be a Sequel Hook for Carnage.
Nicolas Cage and John Malkovich were both considered for the role of the Green Goblin.
Spider-Man 3: The Vulture (who would've been played by Ben Kingsley) was originally going to be one of the main villains. Neither Venom nor Gwen Stacy were present in the original planning packet, with a random woman serving the role Gwen later took.
Also, Gwen was originally going to be kidnapped for the final battle, not Mary Jane; Mary Jane would have talked sense into Harry instead of Harry's butler. A line Mary Jane said for this scene was actually used in the trailer: "We've all done terrible things to each other, but we have to learn to forgive each other or else everything we ever were will have meant nothing."
Reportedly, the scene where Marko meets Eddie was quite different from the "90´s Batman" villain team-up that was shown. After seeing Flint pretending to be sand in a playground for his little girl to play on, Eddie comes up and talks to him, and convinces him that his girl may be cured yet, and he will help him get the cash if Flint helps him take on Spider-Man. This, followed by him learning from his daughter that she is irrevocably sick and just wants to die with her dad a good man, makes his Heel Face Turn at the end, and Peter forgiving him, much more credible and poignant.
These Marko scenes most likely were considered, at least somewhere along the line - they were, after all, used in the Peter David novelisation in lieu of what the movie actually gave us. Though YMMV - the novelisation presents Peter and Flint making amends partway through the battle, while the film shows it after Venom is defeated, and it's really up to the audience to decide which is better. Both exist in some form, at least.
It is also rumored that John Jameson was originally to have an appearance, unknowingly bringing the symbiote back from his astronaut mission.
One of the better examples is the wedding of Mary Jane and Peter Parker, done because Stan Lee wanted to marry them in the daily newspaper comic strip. Of course, that didn't stop Tom Brevoort from claiming that One More Day was actually a "fix" to this form of "meddling".
What Could Have Been: Stan Lee has gone on record as saying if Gwen Stacy hadn't been killed off, most like she would've ended up married to Peter. Some stories, like House Of M, have toyed with this idea.
Joe Quesada wanted to bring Gwen back from the dead in Brand New Day but it was decided against.
Young Allies offered Anya Corazon a potential chance to shine. It had a cast with the potential to create a very interesting character dynamics, and which Anya shone through as the most down to Earth, and easiest to relate to character. But it was killed by poorly written out enemies, an uninteresting and almost generic story arc, and a refusal by Sean McKeever to give the team any sort of cohesion in spite of their common purpose and motivations.
It really seemed the team was finally coming together by the 5th issue or so, but by then the series was canceled. The Young Allies have been popping up here and there however, most recently in Spider-Island.
Word of Gay: Mysterio, in some of the spin-off novels.
Jennifer Hale, who was in both TAS and Unlimited, reprises her roles in both series as, respectively, Black Cat and Mary Jane in the first game, then in the second game, voices Rogue
Literally almost everyone else in the two games were voiced by either Daran Norris (Venom, Mysterio, Scorpion, The Punisher, The Human Torch and Captain America in the first game and Shocker, Sandman, and Professor X in the second) or Dee Bradley Baker (Carnage, Rhino, J. Jonah Jameson, and Daredevil in the first game; Electro, Hammerhead, and Beast in the second; and the Lizard in both games, with his alter-ego, Curt Connors, in the second one. Baker would reprise the role of Connors/Lizard in The Spectacular Spider-Man).
In the Japanese version, Shinichiro Miki is Spidey and Rei Sakuma is Black Cat (and also can be considered as an Actor Allusion, since she voices Kuro, a literal black cat in the Super Robot Wars games, not to mention Shampoo who can transform into a cat.
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