8) Freddie Prinze Jr.
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At the tail end of the 1990s, Freddie Prinze Jr. seemed to be on the road to becoming the next big thing, after roles in hit movies like I Know What You Did Last Summer. Unfortunately, despite (or perhaps because of) playing Fred in the live-action Scooby Doo movies, big success didn’t come. It would have, though, if he had nabbed the role of Peter Parker in 2002’s Spider-Man.
Apparently, he was top choice for the part by many in the know – sadly for him, Sam Raimi was not one of them. Speaking about the casting around the time of the film’s release on Howard Stern’s radio show, Prinze said: “Everyone kind of let me know that it was kind of my flick… everyone except the director.”