This will be the million dollar question throughout the upcoming Oscar season. Most agree that Leonardo DiCaprio is long over due for an Oscar win. He has been nominated 5 times.

1993– Best supporting actor- WHAT’S EATING GILBERT GRAPE. (Tommy Lee Jones won for THE FUGITIVE)

2004– Best actor nomination- THE AVIATOR (Jamie Fox won for RAY)

2006 -Best actor nomination – BLOOD DIAMOND (Forest Whitaker won for LAST MAN IN SCOTLAND)

2013 – Best Actor – THE WOLF OF WALL STREET (Matthew Mcconaughy won for DALLAS BUYERS CLUB)

There are several Tumblr pages dedicated to his plight :
Poor Leo Tumblr Page
Leonardo Oscar

This year DiCaprio tries again in THE REVENANT.  Alejandro González Iñárritu’s follow-up to BIRDMAN, last years best picture winner.

Based on the novel by Michael Punke, THE REVENANT is based on true story.  DiCaprio plays Hugh Glass, a fur trapper who is injured in a fight with a bear. His colleague John Fitzgerald played Tom Hardy robs him and leaves him for dead, but Glass survives and promises revenge on Fitzgerald.

The trailer was released this week, officially kicking off his Oscar campaign.