7. Star Wars II Attack of the Clones (2002)
Directed by George Lucas, DiCaprio was supposed to play the role of Anakin Skywalker. DiCaprio went as far as even meeting with George Lucas. However, the star at that time did not feel suited to take the dive. Presumably DiCaprio did not want to be involved with a sci-fi movie as many actors feel that it damages their credibility as serious actors. However, in turning down the role he lost out being a part of one of the most successful movie franchises in the world and he missed out on being a part of an adventure of a lifetime that Lucas based in a galaxy far far away.
8. Hocus Pocus (1993)
Directed by Kenny Ortega we remember Max played by Omri Katz in this film. However, this film that was definitely put a spell on its audiences also saw the audition of a young boy. This young boy put a spell on the director. DiCaprio who auditioned for the part had forewarned the director that he was up for two other movies one of them being What’s Eating Gilbert Grape. He auditioned with the condition that he would most likely not act in Hocus Pocus. Although we cannot imagine Max being played by anyone but Katz, Ortega was absolutely swept away by Leo’s audition and was extremely reluctant to see the young talent go.
9. The Talented Mr. Ripley (1999)
Directed by Anthony Minghella, this film stars Matt Damon and Jude Law. Damon who plays Tom Ripley delivers a brilliant cowering performance of a man who tries to have it all but devolves into nothingness. DiCaprio was initially considered for the role but ultimately dropped. Perhaps his charisma is such that we cannot really imagine him in cowering roles, but it would be really interesting to see how he would portray a devolving character.
10. Batman Forever (1995)
Directed by Joel Schumacher this film casts Val Kilmer as Batman and Chris O’Donnell as his sidekick Robin. However, the role was originally offered to DiCaprio who turned it down after a meeting because he did not want to go into superhero movies at that time. DiCaprio would in the future also turn down more lucrative roles including Star Wars and Spider-Man because they were fantasy genre films and he was unprepared to venture into them. We can only wonder how his career might have turned if he had played the boy wonder.
11. The Dreamers (2003)
Directed by Bernardo Bertolucci, this film is a masterpiece in the exploration of hedonistic lifestyles in the backdrop of the Paris revolutions. The film stars Eva Green and could have starred Leonardo DiCaprio as the Californian student Matthew. However, DiCaprio who was in pre production stages for The Aviator at that time turned down the role and Michael Pitt, an actor with quite a striking resemblance to DiCaprio was cast instead. We don’t begrudge Leo for having given us The Aviator, a fantastic film but we wistfully dream of how the on screen chemistry between Leo and Eva Green would have played out in the masterful hands of Bertolucci.
12. Angels and Demons (2009)
Directed by Ron Howard and based on Dan Brown’s books, this film stars Tom Hanks as professor Langdon. The film could have had an even more powerful star presence if the role of Camerlengo Patrick McKenna had been played by Leo DiCaprio. Leo, it appears, turned down the role despite being personally offered by Tom Hanks a man who he knew from his Catch Me If You Can days. We wonder how DiCaprio would have fared in a cassock but if his performances are anything to go by he would have pulled it off like a charm.