Leonardo di Caprio was one of the most promising actors when he started out in "This Boy's Life." Critics predicted that he would easily win an Oscar within the next ten years.

It's hard to imagine that after 21 years from "This Boy's Life" the actor has yet to achieve that. It's not due to a shortage in good roles. Leonardo has worked with some of the best directors in the industry: Steven Spielberg, James Cameron, Martin Scorsese, Christopher Nolan and even Quentin Tarantino.

He has also won Golden Globes for best supporting actor and best actor. He has been nominated for the Academy Best Actor twice and best supporting actor once. His trophy cabinet is constantly expanding, but it has yet to be graced with the elusive Oscar.

In this year's "The Wolf Of Wall Street" di Caprio will collaborate with legendary director Martin Scorsese for the fifth time. Scorsese used to have diCaprio's distinction of being nominated numerous times and respected as one of the best of his generation, but never winning the Oscar. Scorsese won it in his sixth nomination in 2006 with "The Departed" which also starred diCaprio.

Why does DiCaprio get the snub? According to Awards Daily, 'pretty boys' or 'golden boys' are somewhat of a disability for the Oscars. They point out: "He wasn't nominated for Gangs, or The Departed, or Shutter Island, or Revolutionary Road, or Inception, or J. Edgar, or Django Unchained." DiCaprio was nominated and even won best actor awards from other institutions for those films.

They compare DiCaprio with other golden boys: "Robert Redford, if nominated this year for 'All Is Lost' would only be his second nomination after four decades of work. Paul Newman didn't win Best Actor until 'The Color of Money,' after six acting nominations."

It should also be noted that in 1997's "Titanic," his co-star Kate Winslet was nominated for Best Actress but he was snubbed. Winslet may be a looker, but she is known for her acting rather than being "eye candy." Other actors like Tom Cruise, Brad Pitt and George Clooney have also failed to take one home.

Does the Academy separate pretty boys from 'serious actors' like Daniel Day Lewis (3 wins) or Tom Hanks (2 wins) ? What does it take to cross the line?

Critics say it could be "The Wolf of Wall Street." Leonardo DiCaprio's role as Jordan Belfort, a stockbroker (pretty obvious) who rides the familiar theme of Scorsese's "power corrupts" train seems familiar and predictable, but they take it to epic proportions. From The Wrap's review:  "His performance goes even further, redefining his thespian abilities and branching out his screen presence into new and fascinating territories."

Could this be Leo's year? "The Wolf of Wall Street" opens on Christmas Day in the US.