8) Freddie Prinze Jr.
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.”