7 Times That Leonardo DiCaprio Should Have Won An Oscar

We love Leonardo DiCaprio! And for all those times he didn't win his Oscar, we think he totally got jipped!

In honor of Leo's birthday, we picked the 7 times that he should of won an Oscar. Happy Birthday Leo!

Romeo + Juliet as Romeo (1996)

Romeo goes up against Tybalt (John Leguizamo) and proceeds to give one of his most intense and believable performances as he initially pulls Tybalt's gun to his forehead, then turns it on Tybalt, and then unloads on him, crying and screaming. The sheer terror and tears on his face seemed so real and the fray ended.


Titanic as Jack Dawson (1997)

Leo plays a star-crossed lover again, but in a different realm, as he brings Rose DeWitt-Bukater (Kate Winslet)  up to the bow of the ship, and creating one of the most iconic "romantic" scenes ever. The clip has made such an impact on pop culture, yet was still a very underrated moment in terms of the film as a whole. The best part? Leo and Kate are still great friends, and she even made a joke about the scene when she was out with Bear Grylls when she participated in Running Wild.


The Departed as Billy Costigan (2006) (NSFW Language)

The role of Billy Costigan took a lot of range between the two characters, or really, the two people that Billy had to pretend to be, being a "rat" in the crew. He could play vulnerable, hard, crazy, and lethal all in one snippet.


Inception as Cobb (2010)

In the mind-bending thriller Inception, Cobb takes on a mysterious character, but at the same time, being haunted by his past, becomes consumed by it. In this particular scene, he's seeing how Ellen Page's Character, Ariadne, can create the alternate reality in the dream world. The film won for visual effects and directing, but none for Leo.


Django Unchained as Calvin Candie (2012)

This particular scene goes down in history as one of Leo's most lethal scenes. In this clip, he slams his hand on the table, and accidentally cuts it in real life, and then continues the scene, as he's profusely bleeding from his palm. It makes his character even more scary, as the debonair man screams at his servants, lights his cigarette, and continues, with the bloody palm.


The Great Gatsby as Jay Gatsby (2013)

The best way to describe Daisy Buchanan and Jay Gatsby is that this woman he pined for during all of his years basically moved on without him when he was gone, and Jay spent his entire life trying to get back to her. Bringing the book to life, Leo was able to bring Jay Gatsby into being, and as he reminisced about his life that he dreamed of having with her, he encapsulated the pain and beauty of that long unrequited love.


The Wolf of Wall Street as Jordan Belfort  (2013) (NSFW)

Jordan Belfort is an embodiment of the American corporate system and how it can go wrong. The character is so multi-faceted, and you follow him from his provincial beings to him going all the way up the corporate food chain. Out of all the movies that Leo has been in, this film was one of the films that people never understood why he didn't win an Oscar for it when the character was so dynamic.

Let's hope that within all the work he put in for The Revenant that maybe this will be his win.... if not, he kept that beard for a very long time for a whole lotta nothing.

NEW YORK, NY - SEPTEMBER 21:  Actor/activist Leonardo DiCaprio accepts the Clinton Global Citizen Leadership in Philanthropy Award at the 8th Annual Clinton Global Citizen Awards at Sheraton Times Square on September 21, 2014 in New York City.  (Photo by Jemal Countess/Getty Images)
Leonardo DiCaprio (Photo by Jemal Countess/Getty Images)



Amy Cooper is a writer and pop culture fact nerd, and on multiple occasions has been referred to as a “Walking iPod.”