- Leonardo DiCaprio, This Boy's Life, 1993. The two close pals auditioned...
- Vince Vaughn, Psycho, 1997. Christian Bale, Robert Sean Leonard, Joaquin Phoenix and Henry Thomas were also up for Norman Bates in the nuttiest idea in movie history - director Gus Van Sant re-making the Hitchcock classic, shot for shot. “So no one else would have to.”(!) And with a cameraman and actress who’d never seen the original, work that out. Oh, and Bernard Herrmann’s score “adapted” by two other guys.
- Matt Damon, The Talented Mr. Ripley, 1998. ... and again. They were both rejected by UK director Anthony Minghella.
- Henry Thomas All The Pretty Horses, 2000. Tobey had been up for the role in September 1998, when Leo DiCaprio's agent was talking about $20m!
- Jimmy Fallon, Almost Famous, 2000. “Scheduling was the culprit,” explained writer-director Cameron Crowe. “My writing is sort of deceptively natural to read, but tricky to do with the right rhythm. Tobey knows the rhythm. So does Cusack, and Jason Lee, and a number of others.”
- Ethan Hawke, Training Day, 2001. All the Movie Brats tested to be Denzel Washington's cop partner - although being more interested in the result of other tests. For Spider-Man. Maguire won Jake Hoyt, did two months weapons and muscle training, but then Hawke became free, after all. Leaving Tobey in great shape to spin his web.
- Edward Norton, 25th Hour, 2001. Tobey or not Tobey… He bought David Benioff’s novel, then decided to swing through Spider-Man. Both guys produced, with Norton using every last cent he got from Red Dragon, 2001, to help the finance then film,.,. and his greatest screen work, worthy of Oscars by the brace.
- Henry Thomas, Gangs of New York, 2002. From Steven Spielberg to Martin Scorsese - ET's guardian really grows up!
- Colin Farrell, Hart's War, 2002. Tobey always looked like any older co-stars's lunch. And far too young to be in WWII, much less a POW camp.
- Jeremy Sumpter Peter Pan, 2003. That's how young he looked... PJ Hogan also looked at Heath Ledger and signed a 14-year-old Californian.
- Orlando Bloom, Pirates of the Caribbean: The Curse of the Black Pearl, 2003. Only Americans considered for the true Brit Will Turner were Maguire and Christopher Masterson, younger brother of Danny from The 70s Show, TV, 1998-2006, and quite a Bloom clone.
- Lou Taylor Pucci, Thumbsucker, 2004. When still a big deal project with Scarlett Johansson.
- Jake Gyllenhaal, Jarhead, 2004. Still up for he same roles as DiCaprio 12 years later. Christian Bale and Joshua Jackson were also seen for US marine Anthony Swoff.He who wrote“For most problems, the Marine is issued a solution. If ill, go to sickbay. If wounded, call a Corpsman. If dead, report to graves registration.”
- Nicolas Cage, Hungry Rabbit Jumps, 2010. Endgame picked up Robert Tannen's thriller for Maguire- to star in and co-produce. That was in 2008.All changes meant Cage and Mad Mentele-discovery January Jones.
- James Franco, Rise of the Planet of the Apes, 2010. “The movie you may have been expecting, » said Chicago critic Roger Ebert. “No less, no more.” For the attempt to relaunch the Fox franchise. Tobey had been in the mix for Will Rodman - a tribute to the first Apes scenarist Rodman (ie Rod) Serling.
- Jeremy Renner,The Bourne Legacy, 2011. Three was enough for Matt Damon. The studio did not agree and kept the franchise alive by rebooting Jason Bourne as Aaron Cross - “There Was Never Just One.” But who should play him from 15 hopefuls? Not the ex-Spider-Man, leaving him free to be Nick Carroway in The Great Gatsby. Renner, Hollywood’s new (and young) white hope since The Hurt Locker, was also picked to carry on the Mission: Impossible franchise.
- John Cusack, The Paperboy, 2011. Dropping out of director Lee Daniels’ innocent-on-death-row dramabecause of his Great Gatsby contract caused delays that meant Colombian Sofia Vergara had to quit, as well.Her Modern Family series came first.
- Bradley Cooper, Jane Got a Gun, 2013. Natalie Portman’s fifth outing as a producer ran into all kinds of trouble. Michael Fassbender quit(replaced by Joel Edgerton) after clashes with Scots director Lynne Ramsay. Then, she quit. Then, Jude Law quit Edgerton’s original role - Lynne being the only reason why Law hadagreed to make the Santa Fe Western in the first place. Bridges was the (way) oldest of Law’s potential successors: double the ages of Maguire and Jake Gyllenhaal. (Ramsey’s exit allowed her to join Steven Spielberg’s 2013 Cannes festival jury).
- Cillian Murphy, Transcendence, 2013. Christopher Nolan’s usual cinematographer Wally Pfister was spoilt for choice of stars eager about his directing debut. Murphy had been in the Chris ’n’ Wally shows: The Dark Knight, Inception, The Dark Knight Rises.
- Chis Pine, Z For Zachariah, 2014. Production was halted and by the time all the problems were ironed out, Maguire had reported to another gig. Star Trek’s Pine subbed as Loomis, part of an eternal triangle - which was just a dystopian couple in Robert C O’Brien’s book… and the 1984 BBC TV version