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7 Leonardo DiCaprio movies that should have won the Oscar but didn’t

Talking about some of the best global actors of our generation, Leonardo DiCaprio’s name would consistently grab the top spot. Here are some Leonardo DiCaprio movies with Oscar winning performances, which sadly didn’t make the cut.

The love-hate relationship that Leonardo DiCaprio has with the Academy Awards is almost gut-wrenching. That he could have won the Oscar so many times for so many Oscar-worthy performances kept his fans at the edge of their seats and anticipating every year. That spell was broken in 2016 when he won the Oscar for Best Actor for his film The Revenant and every fan across the world rooted and cheered for him. But even though he didn’t win an Academy Award for his other movies, they did not fall short on the amazing meter.

Let’s take a look at all the Leonardo Dicaprio Oscar winning movies that unfortunately didn’t win one.

Leonardo Dicaprio Oscar winning movies that did not win one

What’s Eating Gilbert Grape

This 1993 film where DiCaprio was all of 19, won him his first Oscar nomination. Starring alongside Johnny Depp, DiCaprio played Depp’s mentally challenged brother Arnie. As a person with a developmental disorder, Leo not only got all the mannerisms right, he was also applauded and acclaimed for his portrayal of Arnie. The film got only one Oscar nomination that year, and it belonged to Leo.

Romeo and Juliet

While there’s nothing Leonardo DiCaprio cannot do, love stories are something he does best. Proof? This 1996 film, starring a young Leonardo DiCaprio with a 10/10 charm. Baz Luhrmann’s modern adaption of the classic Shakespearean romantic tragedy got Leo cement his position in the genre. Even though he didn’t win even a nomination for Oscars or a Golden Globe, the world was getting ready for what they didn’t know was coming.


What came next became a landmark in not only Leonardo DiCaprio’s career, but in the history of Hollywood. His representation of the fun-loving, charming and witty Jack Dawson made us all fall in love with him. This movie received 13 Academy nominations and won 11 of them, making it one of the biggest Leonardo Dicaprio Oscar winning movies of all times. But sadly, DiCaprio didn’t win one for his performance.

Catch Me if You Can

A brilliant movie, brilliant cast, and what’s even better is that it was based on a real story. Based on the life of Frank Abagnale Jr, who fraudulently posed as a pilot, a doctor and a lawyer, and made millions of dollars, DiCaprio was a sight to behold along Tom Hanks. He shines in every frame, but sadly, only won a Golden Globe nomination and no Oscar.

Blood Diamond

This political war thriller set during the Sierra Leone civil war won many, many accolades worldwide. DiCaprio bagged most of them for his portrayal of Danny Archer, a white South African mercenary and gunrunner. The film chronicles the search for a rare blood diamond amid the atrocities of the war and DiCaprio was flawless in his portrayal of the mafia. He won his second Oscar nomination for this film, but sadly, no Oscars.

Shutter Island

A Martin Scorsese psychological thriller, DiCaprio at his best ever, the film already had an incredible foundation. Leo’s portrayal of the flawed, mysterious character in an asylum for the criminally insane on Shutter Island didn’t win him any award or nomination that year even though it was Martin Scorsese’s second highest-grossing film.


Can this list be even complete without the mention of this visually exceptional film? Bringing science-fiction to the ideas of the unconscious, Leo was outstanding as Dom Cobb, a professional thief who extracts information from the subconscious of his targets. Again, he won no award or nomination for his brilliant performance.

Hero and Featured Images: Courtesy Siebbi, CC BY 3.0, via Wikimedia Commons

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