Woulda, coulda, shoulda. Leonardo DiCaprio is no stranger to the Academy Awards. In fact, the 41-year-old actor has received a total of five nominations for Best Actor and Best Supporting Actor by the Academy over the years. But he has yet to take an Oscar home. All might change this year: Up for grabs is the Best Actor award for his role in The Revenant. Will 2016 be this actor's lucky year?

Acting since the age of 5 (his first appearances include the TV shows Romper Room and Growing Pains), Leonardo DiCaprio has ranked up quite a career, acting in the second highest grossing film of all time (Titanic), which incidentally won a record-tying eleven awards that year, but none in the Actor categories.

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Shortly after making his big screen debut in 1991 in the direct-to-film sci-fi horror Critters 3, Leonardo DiCaprio was nominated Best Supporting Actor for his role in 1993's What's Eating Gilbert Grape, portraying mentally handicapped brother of Johnny Depp's character. From there, it was box office hit after box office hit.

Leonardo DiCaprio's second Oscar nomination wouldn't come for another 12 years, for his performance in 2005's The Aviator as the obsessive American film director Howard Hughes. He won the Golden Globe for that performance but lost the Oscar to Jamie Foxx for his performance in Ray. Leonardo DiCaprio then earned another nomination for his role as diamond smuggler in Blood Diamond, but ultimately lost to Forest Whitaker for The Last King of Scotland.

Looking back at Leonardo DiCaprio's career, he should have won an Oscar somewhere right? After all, he poured his blood, his sweat, his tears into these performances. After 5 nominations, most fans believe that this is Leonardo DiCaprio year to win. But does he truly deserve it for The Revenant? Here, we explore other roles Leonardo DiCaprio should have won the Oscar, or at least have been nominated.

The Wolf of Wall Street (2013)

The Wolf of Wall Street

With over a 3-hour runtime and R rating, Leonardo DiCaprio keeps us entertained the entire way through, never providing a dull moment. His powerhouse performance in Martin Scorsese's epic masterpiece is overwhelmingly hypnotic. Above all other roles in his entire career that has deserved the Oscar win, it is Leonardo DiCaprio's portrayal of Wall Street slime bag, Jordan Belfort. The year was 2013, and the 86th Academy Awards held stiff competition for Leonardo DiCaprio as he went up against Chiwetel Ejiofor (12 Years a Slave), Christian Bale (American Hustle), Bruce Dern (Nebraska) and the accolade winner, Matthew McConaughey (Dallas Buyers Club).

The Departed (2006)

The Departed

Leonardo DiCaprio had a busy 2006. While the actor was nominated in the Best Actor category for his role as diamond smuggler Danny Archer in Blood Diamond, his performance in Martin Scorsese's Irish-American mob drama was largely overlooked. The Boston-set crime flick featured a star-studded ensemble cast including Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg and Vera Farmiga. Only Mark Wahlberg was nominated for Best Supporting Actor. Yet not all was lost, The Departed took home four Oscars that night, including Best Picture and Best Director.

Catch Me If You Can (2002)

Catch Me If You Can

The fast-paced Steven Spielberg-directed biographical crime drama starred Leonardo DiCaprio as real life teenager conman and master of deception Frank Abagnale. Starring opposite Tom Hanks and Christopher Walken, Leonardo DiCaprio's brilliant performance demonstrated he could hang with the big guys and has the chops as well as the looks.

Django Unchained (2012)

Django Unchained

Maybe it wasn't a huge role in Quentin Tarantino's homage to spaghetti Westerns, but Leonardo DiCaprio's horrible, slave-driving Calvin Candie was a memorable character. Leonardo DiCaprio's commitment to the ruthless plantation owner even shown through a scene where he slammed his hand into broken glass, cut his hand, blood pouring out-and never did he break character. Isn't there an award for that?

Inception (2010)


Christopher Nolan's mind-bending sci-fi thriller stars Leonardo DiCaprio as a professional thief who enters the dreams of unwitting targets to extract information. While the film was both a critical and box office success, the imaginative and complex plot line is probably what detracted from Leonardo DiCaprio's cunning and thoughtful performance. The Academy ultimately preferred Jeff Bridges' performance as a down-and-out drunk country musician in Crazy Heart over Leonardo DiCaprio's slick and stealthy criminal, leaving Inception to be recognized in the more technical categories.

The Basketball Diaries (1995)

The Basketball Diaries

Based on the autobiographical work of the same name, The Basketball Diaries stars Leonardo DiCaprio as Jim Carroll, a promising high school basketball player who spirals out of control into the abyss of heroin addiction. A gritty and raw performance, Leonardo DiCaprio's ability to fully invest in his character and not hold back so early on demonstrated the power this young actor was to behold.

The Aviator (2004)

The Aviator

Leonardo DiCaprio reunited with his Gangs of New York director Martin Scorsese for The Aviator, about the eccentric film director and aviation pioneer Howard Hughes. While Leonardo DiCaprio won the Golden Globe for his worthy performance, and landed another nom from the Academy, the trophy ultimately went to Jamie Foxx for his performance in Ray.

What's Eating Gilbert Grape (1993)

What's Eating Gilbert Grape

Leonardo DiCaprio received his first Oscar nomination at the young age of 19, for his brave performance in What's Eating Gilbert Grape where he portrayed Arnie, the developmentally disabled younger brother of Johnny Depp's character, Gilbert Grape. The film put Leo on the map in a big way, earning him the Academy nom as well as a Golden Globe nom, and proved this actor could carry a film on his own. While his performance was beyond real and moving, the Award for Best Supporting Actor ended up going to Tommy Lee Jones for his role in The Fugitive.

Titanic (1997)


Titanic not only obliterated the box office (became the highest grossing film of all time, only to be beat by James Cameron's second box office dynamite Avatar years later) but it took home 11 Academy Awards, including Best Picture and Best Director. I guess the acting wasn't As Good As It Gets: Jack Nicholson and Helen Hunt won Best Actor and Best Actress for their roles. It doesn't mean we didn't love Jack and Rose, but I guess we could have heard them say their names a few less times.