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.

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.

Related: Netflix Responds to Possible Oscars Shutout Spearheaded by Spielberg

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)

<strong><em>The Wolf of Wall Street</em></strong>

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)

<strong><em>The Departed</em></strong>

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.