8 Times Birthday Boy Leonardo DiCaprio Should Have Won an Oscar—Will 41 Finally Be His Year?!

Four-time acting nominee is once again getting major buzz for the gritty revenge drama The Revenant

By McKenna Aiello Nov 11, 2015 1:30 PMTags
Leonardo DiCaprio, Oscars Nominees LuncheonJordan Strauss/Invision/AP

We have a guess as to what Leonardo DiCaprio might wish for when he blows out his candles this year.

The A-lister is celebrating his 41st birthday today, and in what has become one of Hollywood's longer-running "WTF?" moments, the actor still doesn't have a single Oscar win to his name.

slew of gorgeous models to party with on vacation? Sure. A reputation as a tireless philanthropist? Check. A teeny-tiny carbon footprint? As much as can be expected. But Leo has been out of luck four times on Oscar night, no matter how deserving.

20th Century Fox

This could all change soon, however, as the birthday boy is once again the subject of early Oscar buzz, this time for his role in The Revenant, which had him eating raw bison liver and sleeping in animal carcasses for his role as a frontiersman seeking revenge after being left for dead by his companions when he's mauled by a bear. Really, his grizzled look alone is Oscar-worthy, but he's being considered a contender because of his actual performance in the Alejandro Gonzalez Iñárittu-directed film.

And yet, if he does finally hoist the Best Actor Oscar in 2016, it should really be a repeat trip to the podium. Here are eight times Leo was robbed of a well-deserved Academy Award:

Paramount Pictures

The Wolf of Wall Street: 

At the 2014 Academy Awards, Leo was nominated for Best Actor for his hyperactive portrayal of fraudulent stockbroker Jordan Belfort. Despite the widespread havoc his character brought to the financial sector, there was something weirdly endearing about DiCaprio as a corrupt businessman. But he realistically didn't stand a chance against the runaway Matthew McConaughey train and everyone nominated for the Martin Scorsese-directed drama went home empty-handed.

Inception:

We thought Leo's blockbuster collaboration with visionary director Christopher Nolan would make him a shoo-in for an Oscar nod in 2010, but the Academy appreciated the effects more than the acting. The brain-bending drama about stealing people's dreams was nominated for eight Oscars and won four, but all in technical categories.

Andrew Cooper/The Weinstein Company

Django Unchained: 

Almost three years later, we still get chills thinking about DiCaprio's downright terrifying performance as cruel plantation owner Calvin Candie. But maybe he made despicable look too easy, because he was inexplicably not nominated and the Best Supporting Actor statue instead went to his nemesis in the film, Christoph Waltz.

Miramax Films

Gangs of New York:

The 19th-century mob drama's star-studded cast also included Daniel Day-Lewis, Cameron Diaz and Liam Neeson and, while DiCaprio capably led the film and made filthy-and-violent look as desirable as possible, all the buzz in the world was about Day-Lewis as vicious crime boss Bill "The Butcher" Cutting. So wasn't everyone all the more surprised on Oscar night when Adrian Brody came away with the win! But at least Gangs marked the first of the five (and counting) films DiCaprio has starred in for Scorsese, who's directed the thesp to Oscar-worthy performances at every turn, particularly in...

The Aviator: 

This 2004 film spawned a staggering 11 Oscar nominations and went on to win five, but shockingly none of them went to DiCaprio (who was at least nominated) for his unforgettable transformation into filmmaker and aviation pioneer Howard Hughes. And Leo really reached within to channel the character-in-every-sense-of-the-word, famously incorporating some of his own OCD tendencies to play the infamously eccentric Hughes.

ZUMA Movie Stills Library

What's Eating Gilbert Grape:

A then 19-year-old DiCaprio earned rave reviews playing Johnny Depp's developmentally disabled little brother and was was nominated for his first Oscar. Alas, the breakout star lost in the supporting actor category The Fugitive's Tommy Lee Jones.

The Departed:

This 2006 Boston-set crime drama might have taken home the Oscar for Best Picture, but the only acting nomination went to Mark Wahlberg. So at least DiCaprio was in good company alongside fellow snubbees Jack Nicholson, Matt Damon and Vera Farmiga.

20th Century Fox

Titanic:

We'll never let go of this one. Jack and Rose's romance will go down in history books as one of the greatest of all time and Kate Winslet was nominated for her half of the epic couple. With 11 Oscar wins in the record book, no one would really notice if someone went in and added the real king of the world to the tally... right? Maybe we'd remember who actually won that night if it had been Leo!

A very happy birthday to you, Leonardo DiCaprio! And Merry Christmas to the rest of us, because that's when The Revenant hits theaters and we can start planning for Oscar night.

Watch: Leonardo DiCaprio Defends "Wolf" at Oscars