Why Christopher Nolan hasn’t won an Oscar yet.
Firstly, the Academy Award is definitely not a stamp of approval for visionary filmmakers. In fact, the patterns suggest quite the opposite.
The three most popular filmmakers since 70s/80s- Steven Spielberg, James Cameron and Martin Scorsese won their Best Directing Oscars in '94, '98 and '07 respectively (that's over 20 years since they started making films). Nolan started in in 98-99.
The list of great filmmakers who never won an Oscar include:
Stanley Kubrick, Alfred Hitchcock, Federico Fellini, Ingmar Bergman, Robert Altman, Terrence Mallick, Sidney Lumet, Brian dePalma, George Lucas, David Lynch, Ridley Scott, Stanley Karmer, Gus Van Sant and many more.
The same reason why Hitchcock, Kubrick, Tarantino have never won one to date. The fact is Oscar Awards lean heavily towards the following kind of cinema
Biopics , Period Epics Dramatic movies , Satire Movies about persons with some disability or other Drama movies based on real life events. War movies( preferably Holocaust, WWII or Vietnam)
That is because most of the Oscar jury is filled with members whose vision of cinema is still stuck in the 50’s and 60’s. In Hollywood’s earlier years, sci fi, thriller, crime, horror were often seen as B movies. And the Academy still considers them that way. This is the reason why a brilliant crime drama like L.A confidential gets overlooked for a sappy Titanic. Or a Pulp Fiction is not even considered. Though Sci Fi movies have been nominated, the Academy still looks at them as some sort of B Genre. As for horror, barring the odd Silence of the Lambs, it is not even considered.
Now let’s take a look at Nolan’s filmography
Memento- A mind bender of a crime thriller, that needed multiple viewings to just understand it. So no way.
Insomnia- A dark crime thriller, with a rather tragic ending not exactly Academy material.
Batman series( Batman Begins, The Dark Knight, Batman Returns)- Again a superhero series at the end of the day, which is not considered a serious genre. Never mind the fact that The Dark Knight explored the concept of vigilantism, super heroism in such an indepth manner.
Inception- Was nominated, but lost out to Social Network. Again the highly complex narrative, which needed multiple viewings could have been a turn off.
Interstellar- This actually was something the Academy should have loved. It had an epic scope, great cinematography, themes of mankind’s survival, father- daughter bonding, but again sci fi is still a no go area.
Apart from Nolan; Tarantino, Linklater, Aronofsky, Wes Anderson, P.T. Anderson, and Fincher have never won a Directing Oscar despite having a cult status. So An Academy Award for Best Director is definitely not a measure of someone's film making abilities.
Secondly, Academy Awards are given to the best achievement in a certain aspect of filmmaking, that particular year. And judging somebody's body of work is very different from judging their particular film that year. So Leonardo DiCaprio as an actor is not compared to other actors. His latest performance is compared to other performances. Leo might have a better track record, but the Academy felt McConaughey's performance in his latest film was better. That decision is debatable. But regardless, this does not prove that a certain actor is better than certain other actors.
And forget Leonardo DiCaprio, Al Pacino was nominated 8 times since '73 before he won Best Actor in 1993 for 'Scent of a Woman'. Meryl streep has been nominated 19 times since '78, and has won only thrice. Leo has had only 4 nominations since '94, thus only 4 chances of winning.
And to be fair to the Academy, apart from The Dark Knight in 2008, no Nolan's film was justifiably better than the films which were nominated. (Slumdog Millionaire/Danny Boyle won that year). But that was not even nominated. In fact, of all the directors mentioned above, Nolan is the only one without even a single Best Director nomination.
That can be attributed to bad luck, or a bias. But given his filmography, it will be tough for the Academy to keep Cristopher Nolan out for long.