Will Smith’s Best Actor win at the 94th Oscars perhaps would have been more dissected if his personal actions that night hadn’t overshadowed the entire event. Instead, the audience saw the A-lister receive his award, give his speech, and shuffle off to face the reactions of everyone watching.
Had that event not happened, the conversation probably would have been more about the role itself in King Richard and how it fits in with his filmography, and why Smith had to wait so long to receive an Oscar. In fact, many award-winning actors have previous roles that all could have won, but with only one Best Actor/Actress award every year, there will always be some overlooked portrayals.
Leonardo DiCaprio – Won For The Revenant – Should Have Won For The Wolf Of Wall Street
Perhaps one of the few remaining genuine movie stars, Leonardo DiCaprio has only one Oscar to his name. It took until 2016 for the legendary actor to finally win and to many, the award felt like a bit of a makeup for past mistakes. While The Revenant is a fine movie and the extent of Leo’s commitment is well documented, there are earlier films where his acting is truly remarkable.
The Wolf of Wall Street and The Aviator should have been easy wins for the young actor, as both performances required an incredible amount of nuance and range that DiCaprio had not shown before and he was miles ahead of his contemporaries, at the time.
Kate Winslet – Won For The Reader – Should Have Won For Titanic
Kate Winslet has a long and storied career and while her performance in The Reader is more than respectable, the film is not as critically acclaimed. The win came after a number of incredible performances from Winslet, including starring in the high concept Eternal Sunshine of the Spotless Mind alongside Jim Carrey.
Her Academy Award win could have come much earlier in her career for her breakout performance as Rose in the blockbuster, Titanic. That role still has the notability as being one of the most successful films of all time and Winslet manages to overshadow James Cameron’s direction and Leonardo DiCaprio’s star turn at the same time.
Morgan Freeman – Won For Million Dollar Baby – Should Have Won For The Shawshank Redemption
The Academy Awards have long been accused of racism or at the least, the inability to admit that BIPOC actors and filmmakers have a more difficult chance of winning. Enter Morgan Freeman, who did not win the coveted award until 2004 with Million Dollar Baby.
The wait would not be so egregious if he hadn’t played Red in the critically acclaimed The Shawshank Redemption. Freeman’s Red not only co-stars but also narrates in what was the first showcase of the power of his voice. Instead, the award went to Tom Hanks in Forrest Gump, who had won the same award the previous year, meaning that this year could have been Freeman’s for the taking.
James Cagney – Won For Yankee Doodle Dandy – Should Have Won For Angels With Dirty Faces
James Cagney may not be as well known now as he was in the heyday of Hollywood known as the Golden Age, but there were decades when Cagney’s face alone would sell out films. His niche was not of the hero but usually the villain in films like Angels with Dirty Faces.
So it is a bit of a surprise that his only Oscar win came later in his career for the musical Yankee Doodle Dandy. This choice to only recognize Cagney after he had made a musical points to a common throughline for the Academy Awards, as they often reward real-life figures over the fictional and heroes over the villains.
Cate Blanchett – Won For The Aviator – Should Have Won For Elizabeth
Cate Blanchett’s first hit film was also her first Oscar nod earning the Best Actress nomination for Elizabeth, where she plays the queen herself. It was a good year for medieval England, as Shakespeare in Love, to the surprise of many, swept many of the award categories, including a win for Gwyneth Paltrow as Best Actress.
But Judi Dench won in the same year for the same role in Shakespeare in Love. While Cate’s performance held up the entire movie and led to an equally acclaimed sequel in 2006, Dench’s Elizabeth only appeared on screen for eight minutes.
Paul Newman – Won For The Color Of Money – Should Have Won For The Verdict
The Color of Money is Martin Scorsese’s foray into sports drama and it is a great offering at that. Tom Cruise and Paul Newman co-star and Newman brings his usual star performance that makes it hard for viewers to tear their eyes from the screen when he’s on. The only problem is that he had been nominated six times before.
His nomination prior to this year was in the 1982 film The Verdict. Newman’s uses all of his charisma and formidable acting prowess to deliver an incredible performance. But in the 1983 Oscar race, competition was just too fierce. Audiences and fans had to wait until the field softened for Newman to finally earn his award.
Whoopie Goldberg – Won For Ghost – Should Have Won For The Color Purple
A victim of The Color Purple’s egregious year at the Oscars, Whoopie Goldberg had to wait for her second nomination for the film Ghost in order to win. Her role in Ghost isn’t bad at all, but her part in The Color Purple is much more powerful and deep.
Whoopie’s win felt to some like the Academy apologizing for their disservice to the 1985 story about Black American women growing up in the early 20th century. That film was nominated for 11 Oscars and didn’t win a single one. Ghost, on the other hand, is much more of a popcorn flick and romantic drama that went on to win three Oscars, including Best Original Screenplay.
Jeff Bridges – Won For Crazy Heart – Should Have Won For The Big Lebowski
It isn’t that Crazy Heart is a bad movie or that Jeff Bridges performance isn’t good but it’s somewhat telling that it took until 2010 for Bridges to win an award after four nominations for arguably more interesting roles.
This award was in the “it’s his time” vein but Bridges in Starman or Thunderbolt and Lightfoot, when he was also nominated, would have been better ways to celebrate the icon earlier in his career. The biggest travesty is that Jeff Bridges was not even nominated for his iconic role as the Dude in The Big Lebowski, probably his best known and most difficult role.
Jessica Lange – Won For Tootsie – Should Have Won For Frances
Jessica Lange didn’t only arguably win for the wrong movie, she won for the wrong movie in the same year. The actor was nominated for Best Actress in Frances and as Supporting Actress for Tootsie. So she still took home hardware that night but in what is considered the “lesser” category.
Tootsie is a very fun film with great performances all around, but it is mostly Dustin Hoffman’s movie. On the other hand, in Frances, Lange takes on the difficult task of playing Frances Farmer, the 1930’s starlet who suffered from mental illness. The role could not have been played by just anyone and Lange brings an incredible amount of raw emotion and vulnerability to the role.
Al Pacino – Won For Scent Of A Woman – Should Have Won For The Godfather Part II
There were two decades between Al Pacino’s first Academy Award nomination and his first win for Scent of a Woman. Any of his six Oscar nominations between this time could be arguably better and more important that his leading part in the 1992 film – particularly, his third nomination for his role as Michael Corleone in The Godfather Part II.
What’s more, Pacino’s win for Scent changed the trajectory of his career. Pre-win, his roles were somewhat understated. After his win for playing the bombastic Lt. Col. Frank Slade, Pacino spent two decades arguably playing each character with same high intensity.
