Sam Raimi’s third Spider-Man movie isn’t held in the highest regard by the fanbase, but it still managed to earn $895 million at the box office despite being the weakest in the trilogy by a considerable distance. A fourth installment was then placed into development shortly after the threequel hit theaters.
David Lindsay-Abaire and Gary Ross rewrote James Vanderbilt’s original draft, but the scribe was nonetheless tapped to begin working on screenplays for the fifth and sixth films as well. Tobey Maguire, Kirsten Dunst, and J.K. Simmons, among others, all had deals in place to return, with Anne Hathaway’s Felicia Hardy and John Malkovich’s Adrian Toomes set to join them, while Dylan Baker’s Curt Conners would have finally transformed into the Lizard.
Shortly after that, the bottom fell out and a reboot was announced instead. Fortunately, Simmons was invited back into the fold for the Marvel Cinematic Universe’s Far From Home, and he admitted to The Hollywood Reporter at the No Way Home red carpet premiere that he was left devastated by the end of the Raimi franchise.
“After the… Sam Raimi trilogy and then when they moved on from there, it was heartbreaking, I’m not gonna lie. And I thought ‘Oh well, that was amazing fun, and I’m so glad I had that opportunity.'”
If the rumors are to be believed, then Maguire will also be making his grand return in No Way Home while Raimi finishes up on Doctor Strange in the Multiverse of Madness, so it’s all worked out pretty well for the original Spider-Man gang in the end.