- Brokeback Mountain (2005). DiCaprio denied a role in this movie, although it is not clear if it was Jack or Ennis. Jake Gyllenhaal/Heath Ledger got the roles. Source, Vulture
- The Talented Mr Ripley (1999). DiCaprio denied the role of Tom Ripley, which then went to Matt Damon. Source, The Guardian
- The Star Wars prequel trilogy (2002-2005). DiCaprio met with George Lucas but ultimately turned down the role of Anakin Skywalker, which went to Hayden Christensen. Source, Time Magazine
- Peter Parker in the Spiderman trilogy (2002-2007). The role went to Leo's good friend Tobey Maguire. Source, Time Magazine
- Robin in Batman Forever (1995). Chris O'Donnell took the role. Source, Time Magazine
- Neo in The Matrix (1999). DiCaprio initially said yes to the role, but then declined, saying he did not want to do a film that relied so much on visual effects so soon after Titanic. The role went to Keanu Reeves. Source, TheWrap
- Patrick Bateman in American Psycho (2000). Lionsgate wanted DiCaprio or another famous star in the role and was even willing to pay him 20 million USD, although Mary Harron opposed this decision, as he was too 'boyish'. DiCaprio was even announced by Lionsgate as being cast as Bateman; after a lot of behind-the-scenes conflict, DiCaprio eventually left citing creative differences, and Harron's choice of the relatively unknown Christian Bale was finally cast. DiCaprio left to film The Beach instead. Source, The Guardian
- Steve Jobs in the eponymous film (2015). He was approached to star, but ultimately did not join the project. Michael Fassbender was cast. Source, Variety
Do you agree with Leo on passing on these roles, and are you happy with the performances by the other actors? 'American Psycho' was probably the one closest to having Leo. What do you think Leo would've been like in these roles? He's been in so many iconic films and would have been in more had he taken on these roles, but they could also have led him down a completely different career path.
by peachgothlover