Which film should Leonardo DiCaprio have won the Best Actor Oscar for ahead of The Revenant?

Howard Hughes...Frank Abagnale Jr...J. Edgar Hoover?

Leonardo DiCaprio is almost certain to take home Best Actor at the 88th Academy Awards (UPDATE: it happened), ending a narrative that’s loomed so large over recent ceremonies that I’ll be amazed if Leo doesn’t reference it during his acceptance speech.

Ironically, given how he’s been overlooked by the Academy time and time again, it may well be a case of them overhyping his performance in this instance, or at the very least giving him the prize as an acknowledgement of the tremendous body of work he’s built up rather than a plaudit for the film in question. The man himself hinted as much this week.

He’s great in The Revenant, giving a guttural performance that is somehow frail yet mighty, but it’s hard not to agree with the sentiment of The Onion’s ‘Leonardo DiCaprio Hopes He Screamed And Cried Good Enough In The Revenant To Win Oscar’ story that's being shared widely this week.

The Revenant - Trailer

What year then, should he have one? Let’s look at the options:

2005

Jamie Foxx – Ray as Ray Charles - WINNER

Don Cheadle – Hotel Rwanda as Paul Rusesabagina

Johnny Depp – Finding Neverland as J. M. Barrie

Leonardo DiCaprio – The Aviator as Howard Hughes

Clint Eastwood – Million Dollar Baby as Frankie Dunn

2006

Forest Whitaker – The Last King of Scotland as Idi Amin - WINNER

Leonardo DiCaprio – Blood Diamond as Danny Archer

Ryan Gosling – Half Nelson as Dan Dunne

Peter O'Toole – Venus as Maurice

Will Smith – The Pursuit of Happyness as Chris Gardner

2013

Matthew McConaughey – Dallas Buyers Club as Ron Woodroof - WINNER

Christian Bale – American Hustle as Irving Rosenfeld

Bruce Dern – Nebraska as Woody Grant

Leonardo DiCaprio – The Wolf of Wall Street as Jordan Belfort

Chiwetel Ejiofor – 12 Years a Slave as Solomon Northup

Discount Blood Diamond, an eminently watchable yet strangely forgettable film.

2013 then? There was a wave of dislike towards The Wolf of Wall Street at the time (probably because of those screenings filled with cackling bankers - not DiCaprio or Scorsese’s intention) but it seems to have dissipated since and there’s a lot to love about the movie. It might be a little too long and have pulled out of an emotional punch that Up in the Air and The Big Short both landed, but these aren’t problems with the performance. From the mania of the Quaalude scene to the chest-thumping charisma of his stage addresses to employees, DiCaprio was absolutely hypnotic. That said, Matthew Mcconaughey did manage to upstage him slightly in the very same movie, so we’ll let him have his Dallas Buyers Club win.

The Aviator. This is probably the film most DiCaprio fans would settle on. An epic, hyper-cinematic, crumbling castle of a movie built around a jaw-dropping performance from Leo. Braggadocious business tycoon Howard Hughes was typical DiCaprionian stuff in the first half of the movie, but it’s the second where he goes all out, locked in a screening room, bedraggled and crippled by OCD, pissing into empty bottles and watching the same movies on repeat.

There are also several roles it’s amazing DiCaprio didn’t even get a nomination for. Catch Me If You Can for instance, which suffered due to it coming out the same year as Gangs of New York (which Daniel Day-Lewis got the nod for), when in a quieter year he surely would have stood a chance. J Edgar, The Departed and Shutter Island were all unrecognised performances too.

Still, DiCaprio is in good company on the ‘never won an Oscar list’, which also includes Edward Norton, Brad Pitt, Sir Ian McKellen, Tom Cruise (remember, he actually made good films once upon a time) and Bill Murray.