Leonardo DiCaprio: 7 Movies He Should Have Won an Oscar For

Leonardo DiCaprio is one of Hollywood’s living legends and has starred in several high-grossing movies. His movies have grossed about $7.2 billion globally, and his name is a box office earner.

Yet, Leonardo DiCaprio has only won one Oscar throughout his 33-year acting career. Yes, that’s right; one! It came as a relief for fans, colleagues, and well-wishers when he finally broke his Oscar curse at the 88th Academy Awards in 2016. In what could only be described as a miracle, the actor won the Oscar for his role as Hugh Glass in the 2015 movie, The Revenant.

Like the drought and curse that followed him prior to the 2016 Oscars, Leonardo DiCaprio is yet to bag another. In honor of the legend, here are some of his top movies where Leonardo DiCaprio deserved an Oscar win.

Baz Luhrmann’s “Romeo + Juliet” (1996)

Leonardo DiCaprio

Credit: Romeo + Juliet

Romeo & Juliet is one of Shakespeare’s most popular tragedy novels. So, when Baz Luhrmann decided to make a modernized adaptation of it into a movie, it received an all-round success. It was critically acclaimed and grossed $147.6 million at the box office on a $14.5 million budget.

Leonardo DiCaprio played the character of Romeo, much to the delight of fans and viewers. Unfortunately, although he delivered exceptionally, Leonardo DiCaprio was not nominated in any category at the 69th Academy Awards.

Titanic (1997)

Leonardo DiCaprio

Credit: Titanic

Undoubtedly the movie that shaped young Leonardo DiCaprio’s acting career. Titanic was written, produced, and directed by James Cameron. The film was an instant success and became the highest-grossing film until James Cameron decided to break his record with his 2010 Avatar.

With a record budget, at the time, of $200 million, the movie grossed $2.202 billion at the box office. Leonardo DiCaprio played one of the movie’s protagonists, Jack Dawson. Although the movie and its production team were nominated and won in their categories, Leonardo DiCaprio was not nominated in any category for his performance.

The Man in the Iron Mask (1998)

Leonardo DiCaprio

Credit: The Man in the Iron Mask

In retrospect, there are a handful of actors who can deliver roles in Box Office hits back-to-back as Leonardo DiCaprio did in 96′, 97′, and 98′. The Man in the Iron Mask had mixed reviews among critics but delivered at the box office. With a budget of $35 million, it grossed around $183 million.

Leonardo DiCaprio played dual roles as Philippe Bourbon and King Louis XIV. Unfortunately, despite its success, Leonardo DiCaprio’s characters weren’t enough to earn a nomination.

The Aviator (2004)

Leonardo DiCaprio

Credit: The Aviator

Leonardo DiCaprio played Howard Hughes alongside other notable Hollywood actors. The Aviator received positive reviews from critics but was less successful than the other films on this list. The movie earned $213.7 million at the box office against a budget of $110 million.

The movie went on to receive eleven awards, including Best Actor and Best Supporting Actress. Although expectations were high for Leonardo DiCaprio, the movie went on to win five of its eleven nominations, with Leonardo DiCaprio failing to win his.

What was more surprising was Cate Blanchett winning the Best Supporting Actress as Katharine Hepburn. Leonardo DiCaprio’s curse still lingered.

Django Unchained (2012)

Leonardo DiCaprio

Credit: Django Unchained

Quentin Tarantino’s Django Unchained did wonders at the Box Office. It raked in $425.4 million with a budget of $100 million. Leonardo DiCaprio played the character of Calvin J. Candie, the slave master of Django’s wife. The movie bagged some awards at the 85th Academy Awards, but Leonardo DiCaprio was not nominated in any category.

The Great Gatsby (2013)

Leonardo DiCaprio

Credit: The Great Gatsby

Up until his 2022’s Elvis, Baz Luhrmann’s highest-grossing film was none other than The Great Gatsby. With a budget of $105–190 million, the film grossed $353.6 million at the box office.

Leonardo DiCaprio played the movie’s lead role as James Gatz and Jay Gatsby. The movie only received two nominations at the 86th Academy Awards, but luckily won both. Unfortunately, Leonardo DiCaprio’s performance as Gatsby was not enough to even earn him a nomination for that year.

The Wolf of Wall Street (2013)

Leonardo DiCaprio

Credit: The Wolf of Wall Street

Even critics loved the movie, as well as Leonardo DiCaprio’s performance as Jordan Belfort. The Wolf of Wall Street was also a financial success grossing $392 million on a budget of $100 million. Leonardo DiCaprio was nominated in the category of Best Actor at the 86th Academy Awards. However, he lost it to Matthew McConaughey for his role in Dallas Buyers Club.

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