ByCindy Ramirez, writer at
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Cindy Ramirez

Leonardo DiCaprio has almost touched the golden statue that represents the biggest award in the film industry 5 times already. With 1 nomination as a Best Supporting Actor and 3 nominations as Best Actor, he has slowly clapped, smiled and kept his cool as one of the other deserving nominees steps up to the stage and receives an Oscar.

The ceremonies celebrating the best in film for1993, 2004, 2006, 2013 were not the moment of glory for Leonardo, but could this year's ceremony honoring the best in the industry of 2015 be his chance?

I surely hope, but I can only hope.

Let's go over the men that tragically have taken Leo's chance.

66th Academy Award

The year is 1994, the Academy is ready to award the best films and actors of 1993. DiCaprio who wasn't even 20 years old received his first nomination for the movie "What's eating Gilbert Grape" a film where he played the mentally handicapped brother of protagonist Gilbert (played by Johnny Deep).

Young Leo faced strong competitors such as Ralph Fiennes (Schindler's List), John Malkovich (In the Line of Fire), Pete Postlethwaite (In the Name of the Father) and that year's winner Tommy Lee Jones (The Fugitive).

Let's look at Leonardo's face in that first time not receiving an Academy Award.

Leo's young teenager face.
Leo's young teenager face.

And let's take a look at that year's winner acceptance speech. Tommy Lee Jones.

77th Academy Awards

The year is now 2005, a little more than a decade later, now a young but mature Leo has received a second nomination for an Academy Award, this time for Best Actor. This nomination certainly highlights his talent. At this point, Leo is a powerful star still at top of his 90s start-power, but testing more mature roles. In a year that was highlighted by Biographical Films, Leo was nominated for his performance as Howard Huges in the film "The Aviator".

His competitors that year were fierce and popular, a wonderful combination of magnificent stories that gave us nominees such as Don Cheadle (Hotel Rwanda), Johnny Deep (Finding Neverland), Clint Eastwood (Million Dollar Baby) and that year's winner Jamie Foxx for his magnificent performance as Ray Charles, in Ray.

Leo's second loss.
Leo's second loss.

79th Academy Awards

Leo is back in the game, his second nomination for Best Actor puts him in the competition for his performance as Danny Archer in "Blood Diamond", however, it is a difficult year as well.

His competitors this year are talented figures like Ryan Gosling (Half Nelson), Peter O'Toole (Venus), Will Smith (The Pursuit of Happiness) and the winner of the night was Forest Whitaker for his incredible performance as a tyrant dictator in "The Last King of Scotland".

Sadly I have to say it was a deserved win for Forest, but it was a sad loss for Leonardo whose chances will continue to increase, but yet his Oscar moment has not arrived.

So close, and yet so far.
So close, and yet so far.

86th Academy Awards

Due to the age of the internet and Social Media this year loss was not only one that Leo remembers as the 4th time he was nominated for an Academy Award, he will also remember it for the incredible amount of memes that exploded after he was not the winner of the night.

Leo's incredible performance as Jordan Belford in "The Wolf of Wall Street" was critically acclaimed, but we have to admit, it was a difficult decision as well, the competitors this year were figures such as Christian Bale (American Hustle), Bruce Dern (Nebraska), Chiwetel Ejiofor (12 Years a Slave) and the winner of the night was none other than Matthew McConaughey for his performance as Ron Woodroof in the film "Dallas Buyers Club", a wonderful drama that had McConaughey transform to bring this character to life.

Leo's well-practiced serene facade.
Leo's well-practiced serene facade.

88th Academy Awards, could it be Leo's night?

Leo, I do hope this is your year, if there's something we can learn by looking at the previous winners that went out with an Academy Award that night was that transformation was an important part of the role, and this year's "The Revenant" had Leo suffering for his art and transforming to bring a character to life more than he ever has before, but so have some of the other nominees.

And just as a refresher, here are the nominated actors that will be facing Leo in what could be his night.

Bryan Cranston for his role as Trumbo Dalton in "Trumbo"

Matt Damon for his role in "The Martian" as Mark Watney

Michael Fassbender for his role as Steve Jobs in "Steve Jobs"

Eddie Redmayne for his role in "The Danish Girl" as "Lili Elbe"

And now see Leo's transformation...

What do you think? Is this his year?


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