1. 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
  2. The Talented Mr Ripley (1999). DiCaprio denied the role of Tom Ripley, which then went to Matt Damon. Source, The Guardian
  3. 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
  4. Peter Parker in the Spiderman trilogy (2002-2007). The role went to Leo's good friend Tobey Maguire. Source, Time Magazine
  5. Robin in Batman Forever (1995). Chris O'Donnell took the role. Source, Time Magazine
  6. 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
  7. 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
  8. 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.

Posted by peachgothlover

27 Comments

  1. Vegetable-Kiwi-4675 on

    I feel like he made the right choice every single time. Some of the actors gave iconic performances in their roles. Glad we got to see them.

  2. Prudent-Pressure2146 on

    I don’t see him as Bateman at all. I’d have liked to see his take on Ripley (although Matt Damon killed it)

  3. jennifercathrin on

    You mean we could have seen Leo (potentially) getting dicked down on a mountain???

  4. I think his career has been fine regardless. Would love to see him do a Fincher film.

  5. MayaDaBee1250 on

    He was right to decline each and every one of these. But it also just feels like they were just offering him any role for a young male lead/co-lead because he was the biggest star at the time.

    Will Smith also famously declined the role of Neo in the Matrix because he didn’t understand the script. 😭 He regrets that decision.

  6. kawaiihusbando on

    Did they offer leo the neo role afterĀ smith declined or did they offer will smith the neo role after Leonardo DiCaprio declined?Ā 

  7. I actually can see Star Wars & Jobs movies. However, he’s had a likely a better career not doing the CGI type movies.

    It’s interesting Clooney’s & DiCaprio’s have kept they ā€˜mystique’ and to me it’s difficult to understand how or why movie studios are no longer interested in creating new movie stars.

  8. readingalldays on

    I’m suprised he turned down star wars. He is a massive fan. But it also makes sense cuz he never wanted to do franchise or sequels. It’s suprising he knew it would hurt his career from such a young age.

  9. Every film was better for him not being in it. I’m sure he’d have been great, he always is, but I can’t imagine him replacing any of these people. All of these roles are basically iconic, and I don’t use that word lightly.

  10. Going from Titanic to American Psycho in 2 years would’ve had a lot of confused 12 yo girls watching.

  11. Eames_HouseBird on

    He wouldn’t have made a convincing Tom Ripley, no one looks at (post-Titanic) Leo and thinks: “That’s an unpopular, insecure, socially awkward guy”.

    Matt Damon had that combo of charm, sliminess and insecurity that made him the perfect Ripley.

  12. I remember watching an interview with an actor I can’t remember who, maybe Bale? Who said that every male role in Hollywood gets offered to Leo first.

  13. Couldnotbehelpd on

    Was he offered these roles, or approached? Because those are very, very, very different things.

  14. Shoddy_Equipment_561 on

    I don’t think Leo turned down American Psycho, I believe he actually loved the script.

    It was the director (Mary Harron) who was adamant that Christian Bale play the lead role.

  15. LovableDazzling2 on

    It’s wild how casting choices can completely change a movie’s vibe, sometimes the ā€œwhat ifā€ version feels just as iconic as the one we got.

  16. Formal_Chance_4266 on

    I think all of them were good decisions on his part tbh. He’s got a pretty excellent resume and career so if I were him I’d have 0 regrets.Ā 

  17. He really is that guy. These are all iconic roles. (Except maybe robin! ) The fact they all wanted him for this speaks volumes.

  18. NotADeadTurtle on

    I wonder if they hired the young Anakin Jake Lloyd in anticipation of Leo taking the role in the next movies. He looks strikingly similar to DiCaprio

  19. take_the_basterl on

    forever grateful that we got hayden as anakin šŸ¤ž I know the guy got lots of flack but his performance was phenomenal in ROTS

  20. Robert Downey Jr said he turned down The Matrix to do some indie movie and he started to regret it when he was sitting in prison LMAO

  21. colinisthereason on

    I think Christian Bale once said that a lotta peoples’ most famous roles they got, because Leo passed

  22. queefersutherland1 on

    Hayden was absolutely perfect as Anakin and having Leo play that part would have completely ruined it.

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