Leonardo DiCaprio is one of the most esteemed actors of his generation. In fact, he is widely regarded as one of the greatest actors of all time. With an Oscar win and 5 further nominations to show for his prestige, it’s more than fair to say that he is one of Hollywood’s finest thespians.
Throughout his illustrious career, Leonardo DiCaprio has worked with some of cinema’s greatest creative minds. However, compared to his peers, his filmography isn’t as jam-packed. This is because he chooses his projects wisely, typically only starring in one movie a year, sometimes even less. Being so selective with his projects, it comes as no surprise that the Titanic star has turned down many roles, some of them he admits to regretting. So, here are 5 big movies roles he passed on.
Boogie Nights (1997)
Boogie Nights follows the journey of Eddie Adams (Mark Wahlberg), a young man lost in life who finds his calling when a porn producer scouts him out. While a somewhat murky world to cover, Paul Thomas Anderson managed to craft a compelling drama that was littered with humor and heart, landing himself an Oscar nomination for Best Original Screenplay, and directing two of his supporting actors to nominations as well. Although Mark Wahlberg has since expressed regret for his choice to portray Eddie Adams, many consider it to be one of his finest ever roles. And that critically acclaimed rendition nearly went to Leonardo DiCaprio.
At the time of the film’s pre-production, DiCaprio wasn’t quite yet a major recognisable star with audiences, but industry professionals had took notice after his Oscar-nominated role in What’s Eating Gilbert Grape (1993). To that, the role of Eddie Adams came his way, but due to a scheduling conflict with Titanic, he had to pass. Instead, he recommended Wahlberg, who he had just worked with on The Basketball Diaries. Today, DiCaprio calls his rejection of the movie his “biggest regret”, but maintains that Wahlberg’s rendition is stellar, calling the film “a profound movie” of his generation.
The Talented Mr. Ripley (1999)
One of the most interesting Leonardo DiCaprio movie roles that never was is The Talented Mr. Ripley. This is interesting because it feels like a film that could have been the right move for an actor coming off the success of a major blockbuster who wants to prove his dramatic ability. Titanic dominated the Oscars in 1998, winning 11 awards, including Best Picture. However, what stunned many was DiCaprio not landing a nomination for Best Actor in a Leading Role. To that, a movie like The Talented Mr. Ripley would have been the perfect affair for his dramatic flair to shine centre forth without being overridden by huge set-pieces. Although DiCaprio was approached for the role of the infamous anti-hero, he chose to play a character closer to the protagonist realm in Danny Boyle‘s The Beach. It would then take him over a decade to finally step into villainy in Quentin Tarantino‘s Django Unchained (2012).
The Matrix (1999)
The Matrix is perhaps the biggest movie role Leonard DiCaprio turned down. Grossing over $460 million worldwide on a $63 million budget, this masterclass in action and sci-fi was not just a blockbuster but was also widely adored by critics. Three sequels followed, Keanu Reeves became an even bigger star than he already was, and action movie expectations got completely flipped on their head. And Leonardo DiCaprio could have been a part of all of that if he didn’t turn down the role of Neo.
According to producer Lorenzo di Bonaventura, DiCaprio’s decision to pass on The Matrix came down to timing and creative concerns. Having just completed the visually spectacular but demanding production of Titanic, DiCaprio was reportedly hesitant to immediately dive into another effects-heavy blockbuster. The actor met with di Bonaventura and the Wachowski Brothers but ultimately felt he needed a break from the technical complexities and green-screen work that would define The Matrix. Before Reeves took on the role and DiCaprio turned it down, other actors in contention were Will Smith and Brad Pitt.
American Psycho (2000)
American Psycho was the movie role that catapulted Christian Bale to superstardom, going on to star in many movies that became iconic, such as The Dark Knight trilogy. However, despite his later recognition and Oscar win for The Fighter, his disturbing yet enthralling role of Patrick Bateman is perhaps his most enduring. The role of the wealthy New York investment banker with a penchant for extreme violence was initially intended for Leonardo DiCaprio. Yet, this broke down for multiple potential reasons.
Originally, Oliver Stone was onboard as director, and he and DiCaprio reportedly clashed creatively. Mary Haron eventually replaced Stone and was rumored to have concerns with DiCaprio’s “teenage girl” fanbase, fearing they would not take to him playing a psychopath, more specially, one who hurts women. However, in an interview with Vice, co-writer Guinevere Turner claimed that DiCaprio was swayed away from the role by political activist Gloria Steinem.
Spider-Man (2002)
Believe it or not, Leonardo DiCaprio nearly starred as Spider-Man on two occasions. Initially, he was approached by James Cameron. The film would have seen DiCaprio play the iconic superhero and square off against Arnold Schwarzenegger as Dr. Octopus. This movie never came to fruition as Cameron and Schwarzenegger opted to make True Lies instead. Ultimately, this Spider-Man story was never picked back up again.
A few years later, Sam Raimi took the helm of Spider-Man. While the role eventually went to Tobey Maguire, who shot to superstardom, DiCaprio was approached beforehand. In an interview with The ShortList, DiCaprio explained his decision to reject the role, explaining how he essentially was reluctant to play a superhero. And this wasn’t the first time he’d turn down the role of a crusader – he also passed on the part of Robin in 1997’s Batman & Robin.
Read Next: Ranking Leonardo DiCaprio’s Oscar Nominated Roles
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