These are the four roles that could have won Dicaprio an Oscar, but didn’t

This German-American biographical drama film starred DiCaprio as Howard Hughes, the American business tycoon, entrepreneur, investor, aviator, aerospace engineer, inventor, filmmaker and philanthropist. His “descent from eccentric billionaire to reclusive madman” earned him a nomination for the Academy Award for Best Actor, his first. However, Jamie Foxx won the award for Ray.

Source

For his portrayal of Danny Archer, a white Rhodesian gunrunner who is in jail for smuggle diamonds, DiCaprio was nominated for an Academy Award just two years after The Aviator. However, the award went to Forest Whitaker for The Last King of Scotland.

Source

Probably the most popular of all his nominations, this movie saw him in the role of Jordan Belfort, a Wall Street broker and later the mastermind of a Penny stock scam, making a huge fortune. All his fans were very sure of his win this time around, but were shocked when Matthew McConaughey was declared the winner for Dallas Buyers Club. The Wolf of Wall Street was also nominated for best picture, and being the producer, DiCaprio could have got this award had 12 Years a Slave not won it for its exceptional story, gripping direction and captivating performances.

Source