The toughest Oscar race this year was for best actor. Right until the awards began, the race was almost certainly down to Chiwetel Ejiofor for 12 Years a Slave and Matthew McConaughey for Dallas Buyers Club. (McConaughey was the eventual winner.) What also seemed certain was that Leonardo DiCaprio was not going to win this year, or possibly any time soon, unless he becomes a different kind of actor, a much less cool one. Cool guys don’t win Oscars.

Although modern coolness emerged out of jazz and spread through popular music, the movies brought cool to the masses by giving audiences unparalleled access to it. Where else can you sit and stare at cool people for hours? The movies have been good to cool, and cool has been good to the movies. So why is it that so few of the actors who have embodied cool have ever won the Academy Award for best actor?

Consider these icons of cool, all of them non-winners: Cary Grant, Richard Burton, Robert Mitchum, James Dean, Steve McQueen, Samuel L. Jackson, Gary Oldman, and Tom Cruise. Paul Newman and Humphrey Bogart won late in their careers, after age had worn away some of their cool. Two other cool winners, Marlon Brando and Jack Nicholson, each received one of their two awards in their fifties.

Being cool does not mean that an actor isn’t great, successful, or popular—quite the opposite, actually. But it does mean that he will struggle to win the Academy Award for best actor. To understand why, we need a definition of cool (no easy task). For that we need to go to the coolest actor working today, Brad Pitt, who has never won an Oscar for acting (though he did accept one last night as a producer of 12 Years a Slave), and has only been nominated twice for best actor in over two decades of work.

How does Pitt embody cool? As the director Andrew Dominik noted in a DVD extra for the 2012 film Killing Them Softly, “When you watch Brad, you always feel like something’s going on under there, but you’re not quite sure what it is. I think that’s the reason he’s a movie star. He has that quality of mystery. He doesn’t invite you to share his position somehow.”

He doesn’t invite you to share his position. That is as good a definition of movie cool as there is. The cool actor invites admiration, envy, and desire, much more than empathy, because he is unreadable. His characters leave you wondering what it would be like to be them, without ever imagining that you could.

On the other end of the continuum is Tom Hanks, an actor who almost always invites you to share his position. The power of Hanks’s performances lies in their ability to communicate exactly what it would be like to the character he is playing, which is why he has succeeded so much at the Oscars. He has been nominated five times for best actor and won it twice, one of only nine actors to do so.

This Pitt-Hanks Continuum can be used to predict how likely an actor is to win an Academy Award. The more like Pitt an actor’s style and roles are, the less likely he is to win. The continuum also explains why the Academy favors actors playing characters who are disabled, mentally ill, gay, or ugly. What is really being rewarded are roles in which actors stretched themselves in order to share a position that has been underrepresented on screen. Actors—who make up a large portion of Academy voters—are dedicated to becoming other people for a living, and have a natural bias toward the kinds of performances that invite audiences to imagine themselves, too, as someone different.