Will "The Crowded Room" win Leonardo DiCaprio his first Oscar? Reuters

The list of great actors who have never won an Oscar spans Hollywood screen legends (Harrison Ford, Glenn Close), blockbuster stars (Tom Cruise, Robert Downey Jr.) and critical darlings (Joaquin Phoenix, Ed Norton). However, no snub seems to rile up more Oscar resentment from fans than Leonardo DiCaprio's.

Despite four nominations over the course of his career -- “What’s Eating Gilbert Grape” (1994), “The Aviator” (2005), “Blood Diamond” (2007) and “The Wolf of Wall Street” (2014) -- Leonardo DiCaprio has yet to take home an Academy Award. But the actor’s Oscar moment might be coming soon, with “The Revenant” and “The Crowded Room” coming down the pipeline.

Given the long list of notable actors who have yet to win, why so much outrage regarding DiCaprio? Peter Knegt, senior editor at Indiewire, says the reason may be that despite the actor’s incredible fame, he has retained his credibility.

It’s rare to have somebody that is so incredibly famous, but is also an incredibly good actor, Knegt says. “He’s continued to take risks. He’s never done the superhero thing; he’s never sold out.”

However, the Oscar has eluded DiCaprio. The reason might be that despite the love from fans, Hollywood has a bias against the heartthrob actor and his offscreen playboy lifestyle.

“Some might be saying, 'He has it all already. Do we really need to give him an award?'” Knegt says.

What will it take for DiCaprio to win?

“Sometimes it seems these A-list actors have to wait a long time. Look at Al Pacino, who had to be nominated seven or eight times before he actually won,” Knegt says.

DiCaprio’s next chance at Oscar glory will come with “The Revenant,” where he will play Hugh Glass, a frontiersman in the 1820 who sets out for revenge against the men who robbed him and left him for dead after a bear attack. “The Revenant” (set for a Dec. 25 release) is directed by Alejandro González Iñárritu, fresh off the filmmaker’s best director and best picture wins for “Birdman” at the most recent Oscars. The film has all the makings of an awards-season success story.

Recently, however, it was announced that DiCaprio will take on a project that seems tailor-made to win him that elusive Oscar: “The Crowded Room.” In the new project, which DiCaprio will also produce, he will play Billy Milligan. Milligan became the first person to successfully employ multiple personality disorder in a criminal defense when he was acquitted of a rape charge in 1978. The role will require DiCaprio to play over 24 different personalities as diverse as a Yugoslavian man and a lesbian woman. DiCaprio has been eyeing the project since 1997, and the challenging role seems like a lock to garner significant awards attention.

Will one of the two new roles finally deliver DiCaprio his Oscar? Knegt says there is no guarantee: “It depends on the competition.”

Knegt says DiCaprio’s age (40, young for an actor) may be a factor. “There might still be a sentiment [in the Academy] that he will still have so many more opportunities.”

Only time will tell if “The Crowded Room” wins DiCaprio an Oscar. With or without an Oscar, however, fans have come to expect a great performance from the actor. With 24 personalities to channel, fans should get that and then some.

Do you think Leonardo DiCaprio will win an Oscar for “The Crowded Room?” Tweet your thoughts to @Ja9GarofaloTV.