There’s no doubt that Leonardo DiCaprio is one of the best actors in Hollywood today. But appreciation for Leo’s talent is always followed by pity that he has never won an Academy Award. Fans seem so empathetic towards the actor that a video game was created called Leo’s Red Carpet Rampage. The side scrolling game allows you to chase the Best Actor Oscar as a 16-bit Leo DiCaprio, with other contenders following closely behind. There’s a buzzing excitement that The Revenant could finally be Leo DiCaprio’s Oscar-winning moment, having won the every other Best Actor award for his portrayal of Hugh Glass. *Fingers crossed*

Here is a list of movies that should have won Leonardo DiCaprio the Oscar:

1. What’s Eating Gilbert Grape (1993)
This has been described as Leo DiCaprio’s breakthrough role. Playing a disabled teen with mental health issues, this role had Academy Award written all over it. Leo was also nominated for the Best Supporting Actor, but the Oscar went to Tommy Lee Jones for The Fugitive.

2. Titanic (1997)
Titanic - BookMyShow

Leo DiCaprio as Jack Dawson captured hearts across the world. His romance with Kate Winslet‘s character will be remembered as one of the most epic love stories for years to come. 

3. Catch Me If You Can (2002)
Leo DiCaprio plays the infamous conman Frank Abagnale, who pretends to be different people, while escaping the FBI. He was nominated for the Golden Globe, but lost to Jack Nicholson for About Schmidt.

4. The Aviator (2004)
Leo played an aviator, an inventor, and a businessman, who goes by the name of Howard Hughes. He completely imbibed the mannerisms of the historical character, getting his first Academy Award Best Actor nomination for this film, but the Oscar went to Jamie Foxx for Ray

5. The Departed (2006)
2006 was a good year for Leo DiCaprio, with two great movies in his kitty. He received a Golden Globe nomination for both. However, he lost the award to Forest Whitaker for The Last King of Scotland.

6. Blood Diamond (2006)
Blood Diamond - BookMyShow

Leo played a smuggler in search of diamonds in the in war-ridden Sierra Leone. This is considered to be one of his best performances. Once again, he was nominated for Best Actor in the Academy Awards. But the Oscar went to Forest Whitaker for The Last King of Scotland.

7. Revolutionary Road (2008)
This movie reunited Leo DiCaprio with his Titanic co-star Kate Winslet and their performance was critically appreciated worldwide. Kate Winslet won a Golden Globe for her role, but Leo was, once again, left empty-handed.

8. Inception (2010)
One of Leo’s most complicated movies till date barely got him a People’s Choice Award nomination for Favorite Movie Actor. This brain-churning tale cast Leo as an international criminal stealing important information from the minds of people. 

9. J. Edgar (2011)
Leo is the primary choice for every biopic. He played FBI director J. Edgar Hoover, earning him a number of Best Actor nominations, namely the Critic’s Choice Awards, Golden Globe Awards, Satellite Awards, SAG Awards, but sadly, he won none of them.
10. Django Unchained (2012)
Leo’s negative role got him a Golden Globe nomination for Best Supporting Actor, but the award went to Christoph Waltz for the same movie.

11. The Great Gatsby (2013)
The GReat Gatsby - BookMyShow

Leo DiCaprio had become a fan favorite! He won the People’s Choice Award for Favorite Dramatic Movie Actor for this film.

12. The Wolf of Wall Street (2013)
We thought 2014 would definitely be his year with this black comedy film, but the Academy Award was bagged by Matthew McConaughey for his stellar performance in Dallas Buyers Club
After a series of setbacks in the Academy, it’s no wonder that his fans feel sorry for the Golden Globe winner. Let’s hope that the Oscar-worthy movie, The Revenant, will be Leo’s lucky charm. Or is he likely to be sidelined once again? 
Wish you all the best Leo! Catch the Oscars live on Monday, at 5.30 AM.
* UPDATE (29th February, 2016)
At the Academy Awards held on 28th February in the USA, Leonardo DiCaprio finally won the Best Actor trophy for his performance in The Revenant. Congratulations, Leo! 

– By Delnaz Divecha