12 Times Leonardo DiCaprio Should Have Won An Oscar

Everyone loves Leonardo DiCaprio. That is, everyone except for the Academy, apparently. The actor has yet to win an Oscar, even though he’s starred in some of the biggest and best films of the past 20 years. It could be because the actor has been struck with bad luck, being pitted against some powerful performances year after year. It could also be because DiCaprio has starred alongside some Hollywood heavyweights whose performances have stood up to his own, not allowing him to stand out as much as he should.

His boyish looks have also held him back from being able to play different roles, and he tends to stick to his comfort zone, not changing his appearance too much for a part. Even so, he knocks out critically acclaimed performances again and again, and every year that he gets the Oscar snub we just want to hug him even harder.

The only golden statues he goes home with after the Academy Awards is the model (or models) he’s dating at the moment. I guess you can’t feel that badly for the guy, but DiCaprio fans will never let go of the hope that he’ll win the Oscar next time. We’ll never let go, Jack.

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12 Titanic (1997)

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DiCaprio was only 22 years old when he landed the part of Jack Dawson in the now classic film, 1997’s Titanic. Alongside Kate Winslet as Rose, the pair played star-crossed lovers who unknowingly head towards disaster.

Titanic is a fictional take on the real life sinking of the ship of the same name. The film was nominated for 14 Academy Awards and won 11; Best Picture, Best Director, Best Art Direction, Best Cinematography, Best Visual Effects, Best Film Editing, Best Costume Design, Best Song, Best Sound Effects Editing, Best Original Dramatic Score, and Best Original Song. Kate Winslet was nominated for Best Actress, but DiCaprio was not nominated for Best Actor. Even though he was nominated for the Golden Globe, he was snubbed by the Academy.

It was DiCaprio’s role as Jack that gave the film its spirit and what makes it so loveable today. Critics and audiences everywhere agreed he deserved to take home the gold for his knockout performance.

11 Gangs of New York (2002)

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2002’s Gangs of New York stars DiCaprio alongside Daniel Day-Lewis, Cameron Diaz, and Liam Neeson. The story centers on a crime boss and his mob in 19th century New York, and deals with the issues of immigration and the Civil War.

Gangs of New York was nominated for 10 Academy Awards; Best Picture, Best Director, Best Original Screenplay, Best Original Song, Best Sound Mixing, Best Art Direction, Best Cinematography, Best Costume Design, Best Film Editing, and Best Actor. The Best Actor nomination went to Daniel Day-Lewis and not to Leonardo DiCaprio, even though DiCaprio was the film’s main character, playing the role of Amsterdam Vallon, who opposes Day-Lewis’ crime boss character.

A positive for the actor is that Gangs of New York was the beginning of a very long, and very successful relationship with director Martin Scorsese. Scorsese would give DiCaprio many other Oscar-worthy roles over the next decade.

10 Catch Me If You Can (2002)

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In 2002 DiCaprio also starred in the crime drama film Catch Me If You Can. The movie was biographical, being based on the life of infamous con man Frank Abagnale, who was so good at what he did that he ended up working for the FBI.

Frank Abagnale himself is a fan of the film, and he’s not the only one. It was released to a positive reception from critics and audiences alike and made over $352 million. No wonder, starring DiCaprio, Tom Hanks, Christopher Walken, and Amy Adams, and directed by Steven Spielberg, the film was bound to be a success.

Another surprising thing about Catch Me If You Can is the fact that DiCaprio wasn’t nominated for the Best Actor Oscar, especially seeing as how he was nominated for the Golden Globe. Christopher Walken was nominated for the Best Actor in a Supporting Role Oscar and the film was also nominated for Best Original Score.

9 The Aviator (2004)

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Leonardo DiCaprio teamed up with Martin Scorsese again in 2004 for the biographical drama The Aviator. DiCaprio took on the role of Howard Hughes, one of the wealthiest people to ever live. He was an aviator, inventor, investor, and businessman who also worked for many different charities and made films, including 1932’s Scarface.

The film displayed Hughes' life in the late '20s and '40s, his rise to fame in Hollywood and his struggles with obsessive-compulsive disorder. Also starring Cate Blanchett, Kate Beckinsale, Alec Baldwin, Jude Law, Gwen Stefani, and Willem Dafoe, The Aviator was nominated for 11 Academy Awards, including a Best Actor nomination for DiCaprio.

The actor lost to Jamie Foxx for his portrayal of Ray Charles in Ray. Although Cate Blanchett won for Best Actress in a supporting role, DiCaprio was denied the win once again. He did win the Golden Globe for Best Actor in a Leading Role in the drama category.

8 The Departed (2006)

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Another mob movie directed by Martin Scorsese, The Departed came out in 2006 and was extremely well received by audiences and had positive reviews from critics. The all-star cast included DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg, Martin Sheen, Anthony Anderson, and Alec Baldwin. The film deals with the Irish mob in Boston, gangsters, FBI agents, and undercover cops. The Departed has made its way to numerous Top 10 lists and grossed almost $300 million worldwide. The film has won four Academy Awards; Best Picture, Best Director, Best Film Editing, and Best Adapted Screenplay. Mark Wahlberg was nominated for Best Supporting Actor. DiCaprio was once again disregarded by the academy, even though he was the lead in the Best Picture of the year.

7 Blood Diamond (2006)

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Blood Diamond also came out in 2006, but was considered at the 2007 Academy Awards. DiCaprio was nominated for Best Actor for the film, and his costar Djimon Hounsou was nominated for Best Supporting Actor, unfortunately neither won. DiCaprio was beat out by Forest Whitaker for his role in The Last King of Scotland, and Hounsou lost to Alan Arkin for his role in Little Miss Sunshine.

The film touches on the struggle of the Sierra Leone Civil War. Blood Diamond did well at the box office and was praised by critics, and DiCaprio was nominated for not only for the Oscar but also the Golden Globe and the Screen Actors Guild Award. Even though the actor didn’t win anything, he was still the leading man in two of 2006’s biggest films, which is an accomplishment in itself.

This has happened once before for the actor, four years earlier, in 2002 (Gangs of New York and Catch Me If You Can) and will happen once again, four years later, in 2010 (Shutter Island and Inception).

6 Shutter Island (2010)

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Teaming up with Martin Scorsese yet again, DiCaprio plays a U.S. Marshal who is looking into the disappearance of a patient from a mysterious and horrifying psychiatric ward in the 2010 film Shutter Island. Critics called the film a work of art, and DiCaprio was able to creep out audiences in a way he never did before. It was somewhat new for the actor, and yet he seemed comfortable being the lead in a thriller, with terrifying twists and turns.

Shutter Island opened #1 in the box office, being Scorsese’s best box office opening to date. DiCaprio won the Teen Choice award for Choice Movie Actor: Horror/Thriller for the creepy role of Teddy Daniels and was nominated for the American Academy of Science Fiction, Fantasy & Horror Films award for Best Actor.

Even though critics agreed DiCaprio gave an Oscar worthy performance, the Academy didn’t give any love to the actor or the film.

5 Inception (2010)

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Inception also came out in 2010, starring DiCaprio, Ellen Page, Joseph Gordon-Levitt, Marion Cotillard, Tom Hardy, and Michael Caine. DiCaprio plays a man who infiltrates the subconscious of people in order to steal important information. This type of corporate espionage is achieved through sharing their target’s dreams.

Inception made over $800 million at the box office. It won 4 Academy Awards, Best Cinematography, Best Sound Editing, Best Sound Mixing, and Best Visual Effects. The film was also nominated in four more categories; Best Picture, Best Original Score, Best Art Direction, and Best Original Screenplay.

DiCaprio wasn’t even nominated for Best Actor, at the Academy Awards, the Golden Globe Awards or the Screen Actors Guild Awards. Both Brad Pitt and Will Smith turned down the leading role in the film, maybe they would have had better luck at the Oscars than DiCaprio did.

4 J. Edgar

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DiCaprio worked with director Clint Eastwood on the 2011 film J. Edgar, a biographical look at the life and work of FBI director J. Edgar Hoover. The cast also includes Naomi Watts, Josh Lucas, Judi Dench, Armie Hammer, and Ed Westwick.

Roger Ebert wrote positive reviews about DiCaprio’s performance in the drama, calling it a “fully-realized, subtle and persuasive performance, hinting at more than Hoover ever revealed, perhaps even to himself” and gave the actor 3 out of 4 stars.

The actor 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. Yet again, the Academy refused to give DiCaprio a second look. He and the film itself were not considered for any Oscar accolades that year.

3 Django Unchained (2012)

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Quentin Tarantino’s 2012 film Django Unchained made over $400 million at the box office. Starring DiCaprio, Christoph Waltz, Jamie Foxx, Kerry Washington, and Samuel L. Jackson, the movie is about slavery in the Old West. DiCaprio takes on the role of an unpleasant human being and plantation owner Monsieur Calvin J. Candie. We’ve never seen the actor tackle such a cruel human being in a film that talks about such a sensitive and serious subject. Yet again he tests the limits of his acting abilities and, of course, yet again gets slighted by the Academy.

Christoph Waltz won the Oscar for the Best Performance by an Actor in a Supporting Role and Quentin Tarantino won the Oscar for Best Original Screenplay. Although, DiCaprio was nominated at the Golden Globes for Best Performance by an Actor in a Supporting Role in a Motion Picture. The violent film failed to bring in a win for DiCaprio, even though he pushed his limits to play such a racist character, apparently having to stop filming a scene at one point because he was so uncomfortable with his lines.

2 The Great Gatsby (2013)

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In 2013, the world was convinced that DiCaprio would finally take home Oscar gold with his role of Jay Gatsby in the Baz Luhrman remake of the classic novel. Unfortunately for the actor, The Great Gatsby was only nominated twice at the Academy Awards, for Best Production Design and Best Costume Design. The film won both awards and DiCaprio went home empty handed. On the other hand, he did win the Australian Academy of Cinema and Television Arts award for Best Actor in a Leading Role, so at least he has something to put on his mantelpiece.

The movie had a budget of $105 million and made over $350 million at the box office. Tobey Mcguire, Carey Mulligan, Joel Edgerton, and Isla Fisher played the supporting roles to DiCaprio’s lead character. A character that DiCaprio says he wanted to play because of “the idea of a man who came from absolutely nothing, who created himself solely from his own imagination” interested him. Maybe you can imagine that you won the Oscar, Leo.

1 The Wolf of Wall Street (2014)

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In 2014, DiCaprio was nominated for the coveted Best Actor Oscar for his portrayal of fraudulent stockbroker Jordan Belfort in the true story of his turbulent life and career. 2013’s The Wolf of Wall Street was nominated for 5 Academy Awards; Best Performance by an Actor in a Leading Role (DiCaprio), Best Performance by an Actor in a Supporting Role (Jonah Hill), Best Director (Martin Scorsese), Best Adapted Screenplay, and Best Picture.

The night ended with no wins awarded to the film, or to DiCaprio who lost to Matthew McConaughey for his role as Ron Woodroof in Dallas Buyers Club. McConaughey also starred in The Wolf of Wall Street alongside DiCaprio, as well as Jonah Hill and Margot Robbie.

DiCaprio did win the Golden Globe for Best Performance by an Actor in a Motion Picture – Comedy or Musical. The film was DiCaprio and Scorsese’s fifth collaboration. Sixth time’s the charm? Here’s hoping.

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