Oscar-Winning Actors Who Deserved Their Award For A Different Role

Anne Hathaway

There are many great actors who’ve never won an Oscar – Ian Mckellan, Alan Rickman (who was never even nominated), Annette Benning, Toni Colette to name a few – but there are some actors who have won an Oscar but some people are left wondering if they got it for the right role.

Al Pacino

Al Pacino in The Godfather
Al Pacino in The Godfather // Credit: Paramount Pictures

What He Won For: One of the all-time greats of acting Al Pacino has any number of roles where he deserved an Oscar, but amazingly the role that got him that award was for Scent of a Woman playing Frank Slade. Pacino is an actor who will take things to 11 and this perhaps gets the better of him in this film.

What He Should Have Won For – Without a doubt Al Pacino deserved an Oscar for The Godfather even if it meant depriving Marlon Brando of it. Michael Corleone not only looks like a different person at the end of The Godfather to the beginning, he is a different person. The audience sees the change he goes through from noble war hero who wants no part of the Mafia to the blood soaked crime-boss who shuts out the woman he loves from his life.

Leonardo DiCaprio

Leonardo DiCaprio in The Wolf of Wall Street // Credit: Paramount Pictures
Leonardo DiCaprio in The Wolf of Wall Street // Credit: Paramount Pictures

What He Won For – It certainly felt like Leonardo DiCaprio was owed an Oscar and eventually he got it for The Revenant. He plays Hugh Glass a fur trapper who suffers and it seemed like it was suffering that won the award. The Academy can be very impressed by the ordeal an actor goes through for their art and this was certainly the case.

What He Should Have Won For – A very different role to nineteenth century man mauled by bear DiCaprio was brilliant as depraved stock broker Jordan Belfort in The Wolf of Wall Street. To me Belfort is one of the most appalling characters seen in cinema who doesn’t actually murder anyone but the performance is stunning and it is very hard to play so unlikeable a character.

Anne Hathaway

Anne Hathaway in Colossal // Credit: Toy Fight Productions

What She Won For – Watching Les Miserables was one of the hardest cinema-going experiences I’ve ever had. Admittedly I’m no fan of musicals but Les Miserables managed to tick all the boxes of why that is. Hathaway was on screen for a total of fifteen minutes and perhaps other performances of hers may be more deserving.

What She Should Have Won For – This is very much a personal choice but Hathaway has never been better than Gloria in Colossal. This film deserves to be seen as one of the best of the 2010s but seems to have passed most people by. Hathaway is a sort-of writer with a drinking problem who finds her way back to her old home-town whilst on the other side of the world a giant monster is rampaging through South Korea. These events are not unconnected.

Reese Witherspoon

Reese Witherspoon in Election // Credit: Paramount Pictures

What She Won For – Witherspoon was very good as June Carter in a Johnny Cash biopic that has not really stood the test of time. Of course in this film it is Cash who is the central character and Witherspoon never gets the opportunity to really shine

What She Should Have Won For – Comedy is harder than drama and these and Witherspoon is a great comic actor and her role as Tracey Flick is in Election is unforgettable. Some aspects of the film have not aged well but it is undeniable that Witherspoon is great, giving a performance of someone who is sometimes on the verge of snapping.

Gary Oldman

Gary Oldman in Tinker Tailer Soldier Spy // Credit: Studio Canal
Gary Oldman in Tinker Tailer Soldier Spy // Credit: Studio Canal

What He Won For – Playing Winston Churchill is a classic Oscar role and something that will appeal to the Academy voters. Oldman’s performance in Darkest Hour was by no means bad but also nothing spectacular

What He Should Have Won For – A role without the fanfare of Winston Churchill but nonetheless a much better performance – George Smiley in Tinker Tailor Solider Spy. Smiley is emotionally restrained to the point of being stationary and I only remember one outburst from him in the film – but that just makes it more effective. Smiley is the sort of character rarely seen in film these days and Oldman plays it perfectly.

Benicio Del Toro

Benicio Del Toro in Sicario // Credit: Lionsgate
Benicio Del Toro in Sicario // Credit: Lionsgate

What He Won For – Del Toro won Best Supporting Actor for playing Mexican police officer Javier Rodriguez in 2000’s Traffic – a solid film but unmemorable.

What He Should Have Won For – Del Toro has a number of roles that would be contenders but his role as Alejandro in Sicario may be my favourite. Alejandro works alongside the Americans battling the drug cartels, his exact position is unclear but it is soon demonstrated that he has no restraint – showing no problems with torture or murder. The subdued anger of Del Toro is something to behold and he is genuinely terrifying.

Also Read: Oscar Worthy Characters : Vito Corleone

Like this article? Get the latest news, articles and interviews delivered straight to your inbox.

Posted by
Richard Norton

Gentleman, podcaster and pop culture nerd, I love talking and writing about pretty much all pop culture.