5. Al Pacino
Al Pacino didn’t win an Oscar until he did Scent of a Woman in the mid-‘90s, long after he had played all of his most iconic roles. First and foremost, he had played Michael Corleone in all three Godfather movies before starring in Scent of a Woman. Okay, the third one was nowhere near as great as the first two, but Pacino’s performance was still engaging – and he didn’t win for any of them. He portrayed the corruption of a good man who went from a wayward veteran with a bright future to the head of a mafia family who had his own brother killed – the Academy had three chances to reward this transformation.
Brian De Palma’s Scarface is a controversial movie, since a lot of people are divided on whether it is a crime movie masterpiece or an ultraviolent slog, but no one is divided on whether or not Pacino’s lead performance as Cuban immigrant-turned-drug lord Tony Montana is fantastic. He sells every scene, like the “bad guy” monologue in the restaurant. Whatever your feelings on the film are, you can’t deny that Pacino’s performance is compelling.
Pacino had also played a conflicted bank robber in Dog Day Afternoon, an unorthodox undercover cop in Serpico, an upstanding lawyer trying to fight City Hall in And Justice for All, a heroin addict in The Panic in Needle Park, and a working-class hero and ex-con looking for a second chance in Frankie and Johnny. The Academy had plenty of chances to give this guy an Oscar before he starred in Scent of a Woman.
4. Dustin Hoffman
It might seem like a long time ago that Dustin Hoffman was first recognized for his talents by the Academy, since he won Best Actor for his starring role in Kramer vs Kramer in 1980, but he had been acting for over a decade at that point.
It was an important decade for American cinema, too: the 1970s. In the late ‘60s and all throughout the ‘70s, American movies got dark and gritty and real. This era drew some fantastic performances out of Hoffman that the Academy never made a peep about. He played the iconic comedian Lenny Bruce, whose lewd and edgy performances broke all kinds of new ground and set the stage for modern standup comedy while his anti-establishment agenda and resulting obscenity trial are seen as a landmark for freedom of speech in America. No Oscar.
Hoffman starred in Straw Dogs, one of the most disturbing and difficult-to-watch movies of all time, as a writer who moves from the city to a rural area and contends with the vicious locals. Whatever you thought of the excessive violence in the movie, it was certainly provocative and you can’t deny that Sam Peckinpah brought out a darkness in Dustin Hoffman that we had never seen before. Still, no Oscar.
He played Carl Bernstein, one of the guys who broke the Watergate scandal, in All the President’s Men, arguably the greatest political movie ever made. And yet again, no Oscar. As Benjamin Braddock in The Graduate, he encapsulated the existential struggles of young men when they finish college and have to figure out where their lives are going to go, and as Ratso Rizzo in Midnight Cowboy, he brought a truly tragic figure to life and created a cinematic icon. And he still went without an Oscar!
Only when he played a dad whose marriage and family life fall apart as a judge decides whether or not he will be able to spend any time with his son did Dustin Hoffman finally get honored with an Academy Award.
3. Kate Winslet
Long before finally winning an Oscar, Kate Winslet had delivered knockout, Oscar-worthy performances in Sense and Sensibility and Heavenly Creatures. She also starred in Titanic, which tied with All About Eve for the most Oscar nominations for a single movie and tied with Ben-Hur for the most wins – but still, the Oscar shelf of Winslet’s awards cabinet remained empty. She was nominated, as was Gloria Stuart for playing the older version of Winslet’s character Rose, but neither of them won.
Above all, if any Kate Winslet performance deserved to be honored with an Academy Award, it was Eternal Sunshine of the Spotless Mind, the mind-bending, melancholic romance directed by Michel Gondry. It was one of the few movies where Jim Carrey didn’t manage to steal the limelight from all the other actors, because he took a more nuanced approach to the role and he had strong support from his female co-star, Kate Winslet.
Winslet’s performance reflected all the heartache and neuroses that come with a breakup as she embodies the manifestation of Joel’s ex as she appears in his mind, at the different stages of his emotional state, and that wasn’t easy for her to pull off.
When Winslet made an appearance as herself in the Ricky Gervais showbiz sitcom Extras, she made a joke about how long she had gone without an Oscar win. In the show, she was making a Holocaust movie to guarantee herself an Oscar. Funnily enough, a couple of years later, she ended up winning Best Actress for The Reader – a Holocaust movie.
2. Leonardo DiCaprio
Leo went so long without an Oscar that it became almost a joke that he was delivering Oscar-worthy performances every year and never winning an Oscar. The fact that DiCaprio was knocking it out of the park every year to tell powerful stories through transcendent performances and never being rewarded for it became an internet meme.
Finally, in 2016, he won Best Actor for his turn as Hugh Glass in The Revenant. As it turns out, all he had to do to finally win one was eat raw bison liver and climb naked into a dead horse’s corpse. But before The Revenant, DiCaprio had thrown himself head-first into a series of dedicated performances in some of the greatest films ever made. He committed himself wholeheartedly to the role of Howard Hughes in The Aviator and portrayed Hughes’ mental downfall honestly and believably.
The list of Oscar-worthy performances delivered by Leonardo DiCaprio is virtually endless: Catch Me If You Can, Django Unchained, Titanic, Blood Diamond, What’s Eating Gilbert Grape?, Inception, Shutter Island, The Departed, Revolutionary Road, The Basketball Diaries, and even more than that.
Before The Revenant, DiCaprio’s best bet at an Oscar was his role as the infamous stockbroker Jordan Belfort in The Wolf of Wall Street, but the problem there was that the Academy look down on, for want of a better word, funny movies. The Quaaludes scene and the boat scene with the FBI agents rank among the finest comedic acting of all time, but the Academy doesn’t respect comedic acting, even if that comedic acting serves a greater purpose of telling a cautionary tale about a criminal lifestyle in an entertaining way.
Perhaps it was a good thing that director Alejandro G. Iñárritu pushed DiCaprio so hard during the production of The Revenant, because the grueling filming conditions managed to draw out the most authentic performance of DiCaprio’s career, and the one that finally won him his much-deserved Oscar.
1. Gary Oldman
Gary Oldman has never phoned it in or given a bad performance in any movie ever. He is always on. He only managed to win an Oscar this year for playing Winston Churchill in Darkest Hour, but it’s not that he stepped it up to play a historical icon – it’s just that Darkest Hour was in line with the Academy’s politics.
Oldman played the villain in Air Force One with the same level of conviction that he used to play Winston Churchill. Every performance given by Gary Oldman has been utterly dedicated. His quieter and more nuanced take on Commissioner Gordon in Christopher Nolan’s Batman trilogy was overshadowed by Heath Ledger’s fierce and unnerving turn as the Joker, but as great as Ledger was, Oldman shouldn’t have been completely overlooked.
He commits himself to every single role and has given a ton of Oscar-worthy performances in iconic roles, whether they’re literary roles like George Smiley or Count Dracula, or true-life figures like Sid Vicious or Lee Harvey Oswald. Oldman’s quiet, unsettling portrayal of Oswald was one of the best things about Oliver Stone’s JFK. Norman Stansfield in Leon and Drexl Spivey in True Romance both rank among the greatest villains in film history and that’s down to Oldman’s psychopathic, yet charming performances as each one.
And yet, Oldman didn’t win an Oscar until his performance as Winston Churchill this year. Still, better late than never.