He's a decent actor, but that baby-face is something that he will have until his 60s. For this reason, it's hard to see him as, say, a father figure or even as a husband. He will always seem like a young man or a kid until he actually reaches grandpa age. People just don't think of him as a middle-aged adult despite the fact that he is 41. However, he is a good actor and, sooner-or-later, he should win an Oscar simply for the daring and interesting roles that he takes on and does well in.
It's sort of like the same reason Tom Cruise hasn't won an Oscar and he is great actor, better than Leonardo DiCaprio.
The Academy Awards have always been a popularity contest and pandered to The Academy's tastes.
The King's Speech won an Oscar and was one of the most boring movies I have seen so far (and I usually like biographical movies).
The very first Oscar was supposed to go to Rin Tin Tin, as he received more Best Actor votes than Emil Jannings, but do you know how quickly the Academy would have been shut down if they gave the very first Best Actor award to a *dog*?
I'm not saying Leo is a dog (though his dating habits may lead people to believe otherwise), but he's probably getting snubbed for the shits and giggles at this point.
Only a part of the Oscars is the quality of the movie or the performance, the rest is politics. There's stories that the voters don't even watch some of the movies like in the animation category because they're too lazy so they just vote for the biggest one. I think he should have have definitely won a Oskar by now.
This has actually been extensively written about. The short version is that Leo plays more challenging characters that don't show you exactly what's on their minds and don't emote as explicitly as, say, Tom Hanks. Read the full story here:
It's because of everything else to do with films and the film industry, the whole industry is done by opinions. That's why awards shouldn't be as in the limelight as they are, because who wins is down to the majority opinion of a minority group. Not everyone will agree with a decision, because not everyone had an input. You can't say someone's the best actor, or a films the best film as it is all opinions. And for the award to be most accurate you would need every person to vote and not just a minority group. And he hasn't won one due to the fact more people had the opinion someone else's performance, in the group who decide. Hence why awards shouldn't be seen as such a big thing, as it's just an opinion of some people that one person was a better actor that year.
Because dying in a movie and doing remakes does not mean he deserves an oscar, any actor can do that
I love Leo, and honestly I don't think he needs this award to have his talent recognized. He's had the luxury of playing great characters and has done it so good. Only a good actor can build a whole different character out of nowhere or from studying who and what they'll portray. That includes the voice and the expressions, Leo has been able to change in every character and that I appreciate in a good actor.
It depends on who's voting. This year looks like his year, though. The Revenant was just ok, in my opinion.