Leonardo DiCaprio is Hollywood’s golden boy. As soon as he broke out with What’s Eating Gilbert Grape in 1993, he embarked on a long ascent that would see him rise to the top of the Hollywood ladder and raise the bar on what it meant to be a leading man in the modern age. From his breakout performance as doe-eyed beau destined for tragedy in Titanic to his last film role as Dr. Randall Mindy in Don’t Look Up, across his career, DiCaprio has shown to everyone that to achieve tangible and consistent greatness, actors need to push themselves into uncomfortable areas.

Whether it be the historical romp, laugh-a-minute comedy or meticulous biopic, DiCaprio has pledged his talent to almost every genre in his extended time in the sun. His next starring role will see him again team up with Martin Scorsese in his long-awaited Killers of the Flower Moon. Also boasting the likes of Robert De Niro and Brendan Fraser, it’s a crime drama based on the 1920s Oklahoma murders committed in the Osage Nation after oil was discovered on tribal land. The film has a lot of promise, with it clear that DiCaprio isn’t planning on letting go of his crown anytime soon.

Outside of acting, DiCaprio is also a producer and political and environmental activist. Regarding the climate, he is one of the most prominent figures using their status to raise awareness about the impending climate disaster. After winning the Oscar for Best Actor for his work in The Revenant in 2016, he said in his acceptance speech: “Climate change is real; it is happening right now. It is the most urgent threat facing our entire species, and we need to work collectively together and stop procrastinating.”

In truth, there are many reasons why Leonardo DiCaprio has remained one of the acting world’s darlings for so long. Remarkably though, when it comes to his stellar filmography, there could have been even more iconic moments if he hadn’t turned some huge roles down. However, such is the life of one the talents of a generation; you can’t be everywhere at once.

Join us as we list five huge roles that Leonardo DiCaprio turned down.

Five huge roles Leonardo DiCaprio turned down:

Dirk Diggler – Boogie Nights (1997)

Boogie Nights is one of the greatest cinematic triumphs of the 1990s. Helmed by the young Paul Thomas Anderson, it charts the rise of a young nightclub dishwasher into a famous porn star known as Dirk Diggler in the 1970s and 1980s, with all the highs and lows included. Famously, it gave Mark Wahlberg his breakout performance, but for a time, it looked as if the role of Diggler might go to Leo.

Years later, Anderson would say that he asked DiCaprio to be in the flick, but that he spent “many, many months” debating whether he should sign on. Eventually, he turned down the role to star in one of the most successful films of all time, that year’s Titanic, which made him a bonafide star. Looking back now, given how instrumental James Cameron’s epic romance was for the heights reached in DiCaprio’s career, we’re sure Boogie Nights is one role he doesn’t regret passing up.

He told GQ in 2008: “I would have been happy to do them both. And the truth is, if I’d not done ‘Titanic,’ I wouldn’t be able to do the types of movies or have the career I have now, for sure … But it would have been interesting to see if I had gone the other way.”

Neo – The Matrix (1999)

The Matrix is an iconic movie franchise, with the role of protagonist Neo now regarded as Keanu Reeves’ defining one. It is virtually impossible to imagine anyone else as the character, let alone DiCaprio. Still, after his performances in Romeo and Juliet and Titanic, he was the most in-demand actor in Hollywood, which led to talks for him to play Neo.

The man instrumental in getting The Matrix greenlit, Lorenzo di Bonaventura, explained to The Wrap in 2019: “Then we go to Leonardo [DiCaprio]. He says yes, we have meetings with him, and then he goes, ‘You know, I can’t go do another visual effects movie having just finished ‘Titanic’ and he drops out.”

You can’t have it all.

Tom Ripley – The Talented Mr. Ripley (1999)

The Talented Mr. Ripley was a critical and commercial success when it was released, with much of this owing to the brilliance of Patricia Highsmith’s original 1955 novel of the same name. It tells the story of Matt Damon’s Tom Ripley, who goes to great lengths to have the plush life of Jude Law’s wealthy playboy, Dickie Greenleaf, and his socialite girlfriend, Gwyneth Paltrow’s Marge.

One of the best performances of Matt Damon’s career; things could have been much different. The Guardian reported in 2000: “Before signing up for The Beach, DiCaprio also turned down the lead role in The Talented Mr. Ripley“.

DiCaprio probably regrets this one greatly. The Talented Mr. Ripley was nominated for a slew of Oscars, whilst The Beach was a dud and is considered one of his worst movies. We all make mistakes, though.

Patrick Bateman – American Psycho (2000)

American Psycho was the moment Christian Bale became an icon. A pop culture classic that satirises 1980s yuppie culture, it sees Bale play the psychotic banker Patrick Bateman in a genius retelling of Bret Easton Ellis’s hit novel. However, the cantankerous Welshman might not have had his break in 2000 if DiCaprio hadn’t decided to pull out. It is widely reported that the studio cast DiCaprio early in production, and they wanted him so bad that they fired director Mary Harron because she insisted on having Bale in the lead role.

In 2020, the film’s screenwriter, Guinevere Turner claimed in Vice that DiCaprio pulled out after the feminist pioneer Gloria Steinem told him not to star in a movie that depicts violence against women, mainly because his fan base was made up of young women.

Famously, Harron was brought back into the fold, and Bale was cast. The rest was history. Eventually, DiCaprio would also get his chance to play a yuppie in Martin Scorsese’s 2013 romp, The Wolf of Wall Street. This time though, there would be much less blood.

Anakin Skywalker – Star Wars: Attack of the Clones (2002)

To imagine anyone but Hayden Christensen as Anakin Skywalker is challenging, particularly given that it’s the only role of note he’s ever had. However, even the young Canadian could have had his past, present and future taken away if DiCaprio had taken on the character following a meeting with Star Wars creator, George Lucas. Speaking to Shortlist, DiCaprio recalled: “I did have a meeting with George Lucas about that as well, yes,” before explaining that he was never interested in the role, despite going to the meeting.

It would have been interesting to see DiCaprio play Anakin and, by proxy, Darth Vader, but he was too busy toughing it up in Gangs of New York and Catch Me If You Can.