#Movies & TV

15 Films Leonardo DiCaprio Should Have Won an Oscar for

by Effie Orfanides

15 Films Leonardo DiCaprio Should Have Won an Oscar for

Leonardo DiCaprio has never won an Academy Award, which is shocking to many fans of the actor. Despite being in some incredible films (and portraying some really awesome roles), DiCaprio is thought to be “cursed” when it comes to the Academy Awards. Sure, he has been nominated—but he has never actually won. With his latest nomination for his role in The Revenant, many wonder if 2016 will be Leo’s year. In honor of his nomination, check out some of the roles that Leo should have won an Oscar for.





In 1997, Leonardo DiCaprio played Jack Dawson in one of the most classic films of all time. At just 22 years old, the actor starred alongside Kate Winslet and got himself nominated for an Oscar. He didn’t win, however. Titanic was nominated for 14 Academy Awards and won 11.


What’s Eating Gilbert Grape?



This 1993 film was one of DiCaprio’s very first movies. This was also the very first time that the talented actor would feel snubbed by the Academy. Although he was nominated for an Oscar (it was his first nomination ever), he lost to Tommy Lee Jones, who won for his role in The Fugitive.


Gangs Of New York



Leonardo DiCaprio starred in this 2002 film that was nominated for 10 Academy Awards, but Leo wasn’t even nominated. In fact, it was Daniel Day-Lewis who got the nomination for Best Actor, even though Leo was technically the main character in the film. The Martin Scorsese–directed film helped bond the two men for life, however, which has been a pretty great thing when it comes to film.


Catch Me If You Can



Also in 2002, DiCaprio starred in Catch Me If You Can. Although his role landed him a nomination at the Golden Globes, he was not nominated for Best Actor by the Academy.


The Aviator



Leonardo DiCaprio was near brilliant when he portrayed film producer and aviation pioneer Howard Hughes. Although the role earned him a nomination (the film was nominated in 11 categories), Leo lost to Jamie Foxx (Ray).


The Departed



It was in 2006 that DiCaprio took on the role of Billy in The Departed. Surprisingly, Leo wasn’t even nominated for his work on the film. The film won Best Picture of the Year, but its leading character didn’t get any recognition by the Academy.


Blood Diamond



This 2006 film got Leonardo DiCaprio nominated for Best Actor. Not surprisingly, however, Leo went home from the Oscars empty-handed again.


Revolutionary Road



Reunited with his Titanic costar Kate Winslet, Leonardo DiCaprio missed an Oscar nomination for Revolutionary Road. Winslet won a Golden Globe for her role, but Leo was left in the dark yet again!


Shutter Island



Many critics thought that Leonardo DiCaprio would be nominated for an Oscar for his role as a U.S. Marshal in Shutter Island, but he wasn’t.





In 2010, DiCaprio put his talents to good use again. The film Inception made over $800 million at the box office and was pretty awesome. Leo’s performance—though pretty great—wasn’t recognized. He didn’t even earn an Oscar nomination!


J Edgar



While this film isn’t a DiCaprio favorite, the actor got plenty of attention for his role. He was nominated for Best Performance by an Actor in a Motion Picture – Drama at the Golden Globes and for Outstanding Performance by a Male Actor in a Leading Role at the Screen Actors Guild Awards. The Academy chose not to nominate him, however.


Django Unchained



This film brought the same sad story for Leonardo DiCaprio. He was nominated for a Golden Globe but snubbed by the Academy.


The Great Gatsby



This film is all anyone could talk about when it was released, and many people thought that 2013 would be Leo’s year. The Great Gatsby was nominated for Best Production Design and Best Costume Design, leaving Leo high and dry—say it with us—again.


The Wolf of Wall Street



2014 may have been the biggest upset of Leonardo DiCaprio’s year. He lost his Oscar nomination of Best Actor to Matthew McConaughey (Dallas Buyers Club).


The Revenant



It’s 2016. Leonardo DiCaprio has been nominated for an Oscar for his role in his latest film, The Revenant. He should win, but will he? Bryan Cranston (Trumbo), Matt Damon (The Martian), Eddie Redmayne (The Danish Girl), and Michael Fassbender (Steve Jobs) are Leo’s competitions. It looks like he’s got this one in the bag (finally). He already won the Golden Globe for Best Actor in this film … but will he break his Oscars curse?