Kevin Spacey Won Best Actor in 2000
Maybe this is a hindsight situation, but Kevin Spacey shouldn’t have won Best Actor for playing a villian in American Beauty. Even in his Oscar’s speech, he goes on to say, “To my friends, for pointing out my worst qualities. I know you do it because you love me, and that's why I love playing Lester.”
Nearly anyone would be a better choice than Spacey. No one should win an Oscar for being gross (and themselves). These days, Spacey hasn't appeared in a film since 2018. While the fallen actor has not yet been convicted on any crimes, it's clear that Hollywood wants nothing to do with him.
Brad Pitt Should Have Won Best Actor in 2000
Fight Club was nominated for one Oscar, but Best Actor should have gone to Brad Pitt. Tyler Durden became one of his most iconic roles. His lines are quotable, and you almost believed that he was who he said he was. He was crazy and was undoubted Mr. Hyde to the Narrator’s (Edward Norton) Dr. Jekyll.
Pitt might not have won the Oscar that year, but, thankfully, he's done better in the ensuing years. In 2014, the film 12 Years a Slave won an Oscar for Best Picture--while it wasn't an individual win, Pitt was stil part of the project. Then, in 2020 he finally got his due with an Oscar win for his role in Once Upon a Time in Hollywood.
Al Pacino Won Best Actor in 1993
Scent of a Woman feels like Oscar bait from the very beginning. All they had to do to win was get an esteemed actor to play in a drama about something very serious and heartfelt. The film feels over calculated, and Al Pacino does a good job in the role. In the end, Best Actor is a stretch since it feels like a dime a dozen.
It turns out that Al Pacino's history with the Oscars is just all topsy turvy. He didn't deserve the win for Scent of a Woman, but he most certainly did deserve wins for The Godfather and The Godfather Part II. However, all he got were measly nominations for those iconic roles.
Denzel Washington Should Have Won Best Actor in 1993
When Denzel Washington lost Best Actor for Malcolm X, it felt like a loss for everyone. Washington was robbed of the award considering this is one of the best films of all time. His speeches were so strong and powerful, and his portrayal of the civil rights leader quickly became one of Washington’s most iconic roles.
However, the Academy has given him his rightful due at other points in his career. In 1990, Washington won the Oscar for Best Supporting Actor thanks to his role in the war film Glory. Additionally, he nabbed the Oscar win for Best Actor in 2002 with his starring part in Training Day.
Anjelica Houston Won Best Supporting Actress in 1986
Prizzi’s Honor was tremendous and Anjelica Houston and Jack Nicholson were like the king and queen of cinema that year. Unfortunately, her Oscar for Best Supporting Actress was misplaced. It wasn’t that it wasn’t deserving of an Oscar, but that there were better options that year.
It seems like the Academy may have cooled to her a bit since her win, because it's the only one she's achieved as of 2021. She received nominations for her roles in Enemies: A Love Story and The Grifters, but she just couldn't seal the deal. That being said, she's got plenty of other awards to keep her warm at night.
Margaret Avery Should Have Won Best Supporting Actress in 1986
There’s no doubt that Margaret Avery should have won Best Supporting Actress for her role as Shug Avery in The Color Purple. According to Avery, some of the hate comes from the film that Spielberg was the director. Apparently, Spielberg was a new director that was given everything, including a studio.
Meanwhile, other directors that had been waiting decades got nothing. That’s no reason to deprive Margaret Avery of her Best Supporting Actress Oscar. It seems more than a little unfair to throw the whole cast and crew under the bus when it's the one director that everyone has problems with.
Elizabeth Taylor Won Best Actress in 1961
There’s absolutely no doubt that Elizabeth Taylor is a wonderful actress. Her role in Cat on a Hot Tin Roof was unforgettable. The only issue is that Butterfield 8 was a bad film, and she didn’t deserve the Best Actress Oscar that year. Currently, the movie sits at a 47% critics Rotten Tomatoes score. Even the audience score sits at 57%, which is pretty low for an Oscar-winning film and performance. The film itself was called “a piece of obscenity.” Even Elizabeth Taylor claimed that the movie was a stinker, saying that she only made it to fulfill her contract.
There are rumors that she may have won the Oscar only because she had been deathly ill with pneumonia. It made her a sentimental favorite, and winners for the Academy Awards are actually chosen based on votes from those involved in the film industry as actors, actresses, producers, and directors.
Shirley MacLaine Should Have Won Best Actress in 1961
The Apartment was considered to be one of the best movies made that year. It sits at a 93% critics score and 94% audience score on Rotten Tomatoes. Jack Lemmon and Shirley MacLaine are no doubt what made this film so great. Their performances alone made this movie a must-see.
There’s no doubt about it that Shirley MacLaine deserved the Best Actress Oscar. That being said, MacLaine has done just fine in the awards department. Her Golden Globe wins stretch all the way back to 1955 when she won Most Promising Newcomer for her work in The Trouble With Harry.
Judy Holliday Won Best Actress in 1951
Born Yesterday had a pretty good concept, and Judy Holliday did a pretty good job as Billie Dawn. The issue lies in the fact that there was better (and overlooked) talent that year. Even if you can get past Judy Holliday’s grating voice, the scenes where she responded Harry’s actions were pretty challenging to understand. It’s just not a Best Actress performance.
But maybe Holliday deserved it just a little bit. It was her one and only win, as well as her one and only nomination for an Oscar. Surely this icon of stage and screen deserved a little recognition in her time. Who can remember back to the 1951 Oscars anyways?
Gloria Swanson Should Have Won Best Actress in 1951
There’s no doubt that Gloria Swanson’s role in Sunset Boulevard deserved the Best Actress Oscar. In this film, Swanson takes huge risks and chances a bit of parody in her performance. Norma is on the edge of madness, and the audience feels it in more ways than one. Not only is this the film of the decade, but it’s also the performance of the decade.
While she never won an Oscar for any of her roles, you've got to look at the silver lining. Sunset Boulevard has gone on to become one of the most iconic American films of all time--who can even remember the movie that beat her out anymore? She did just fine for herself, Oscar or no Oscar.
Julie Christie Won Best Actress in 1966
Julie Christie was the must-have actress in your film. She was young, had talent, but her role in Darling just wasn’t worth Best Actress. Not that it was terrible, but it wasn’t up to par with the competition that year.
Christie might not have deserved this particular Oscar, but she's had a long, successful career that's more than worthy of an award or two. Her first role was all the way back in 1961 on the British sci-fi show A for Andromeda, and she's been steadily working ever since--with her most recent credit being in 2018.
Julie Andrews Should Have Won Best Actress in 1966
Julie Andrews should have won Best Actress for her performance in The Sound of Music. First, The Sound of Music is an iconic, classic film that spans generations. Much of that is thanks to Julie Andrews winning over the audience as Baronin Maria von Trapp. It’s safe to say the movie wouldn’t be the same without her.
But does Julie Andrews really seem like the kind of person to hold a grudge over a decades-old Academy Award loss. The woman is an official dame of the British Empire, for crying out loud. Seems like she's probably got more important things to worry about than a gold statuette.
Glenda Jackson Won Best Actress in 1974
Glenda Jackson won Best Actress for her role as Vickie Allessio in A Touch of Class, but she shouldn’t have. A Touch of Class wasn’t a movie that did well with audiences probably because it makes adultery seem like a not-so-taboo subject. The chemistry between Glenda Jackson and George Segal can’t be denied, but Oscar worthy? Not so much.
This was actually not her first Oscar win--in fact, it was Jackson's second of the decade. In 1970, she also was the award for best actress thanks to her role in the drama film Women in Love. Additionally, Jackson has also won a Tony and an Emmy, making her one of the rare few to achieve a "Triple Crown."
Ellen Burstyn Should Have Won Best Actress in 1974
Ellen Burstyn in The Exorcist should have won Best Actress over Glenda Jackson. The horror on her face was realistic and terrifying, and we were right there with her through it all thanks to her fabulous acting. While she got a nomination, she still lost. It wasn’t a total snub, but it was a mistake on the Academy’s behalf.
While she may have not gotten the Oscar she deserved for that role, Ellen Burstyn lives on in movie history for that iconic role in The Exorcist. I'm sure that all the fame this terrifying classic brought her is worth more than a dozen Academy Awards. Plus, she's had a long and successful career.
Peter Finch Won Best Actor in 1977
I don’t mean any disrespect with listing Peter Finch on this list. His role as Howard Beale in Network was passionate and certainly worth a nomination, but was it worth the Best Actor win? Not compared to the other options on the table.
However, his Oscar win, deserved or not, made major history in the Academy. It was the first Oscar ever given posthumously--Finch unfortunately died of a heart attack while on a publicity tour for the film. The only other actor to ever receive a posthumous Oscar was Heath Ledger in 2009.
Robert De Niro Should Have Won Best Actor in 1977
Taxi Driver released the same year as Network, giving the Academy a problematic choice. In the end, Robert De Niro deserved the Oscar for Best Actor. De Niro made Travis Bickle scary, yet relatable in a way. He may not have won because the movie wasn’t appealing enough because it was from Bickle’s point of view.
In response to that, the film wouldn’t be half as great if it wasn’t for De Niro’s portrayal of the mentally unstable insomniac. Unfortunately, this would not be the last time De Niro was snubbed by the Academy. Only a few years later, he would be nominated but not win the Oscar for Best Supporting Actor in his role for the film The Deer Hunter.
Mary Steenburgen Won Best Supporting Actress in 1981
Mary Steenburgen won Best Supporting Actress for Melvin and Howard. The problem with this is that the character is something we’ve seen from her quite a bit. The character isn’t particularly smart, and some parts felt overacted in the worst kind of way.
We hope that Steenburgen enjoyed her Oscar win, because it's the only one she's managed to get in her career thus far. In fact, she's never even been nominated again since her win for Melvin and Howard. It's the same story when it comes to her record for the Golden Globes as well.
Shelley Duvall Should Have Won Best Supporting Actress in 1981
How did Shelley Duvall not win Best Supporting Actress for The Shining? Not only was Kubrick a perfectionist, but he also got what he wanted out of his cast to make the scenes undeniably pristine. Shelley Duvall would cry every day for 12 hours a day while trying to get the perfect scene. In the end, they couldn’t have picked someone better for the role because Wendy’s fear of Jack and her response to his insanity was out of this world.
It's clear that some people simply were just not fans of Duvall's performance in The Shining. In addition to the Oscar snub, she was actually also nominated for the Razzie for Worst Actress thanks to the role. She didn't win, thank goodness, but it's got to be embarrassing to be nominated.
Marlee Matlin Won Best Actress in 1987
Marlee Matlin won the Best Actress Oscar for her role in Children of a Lesser God. Matlin is an incredibly talented actress, and her performance was worth a nomination. However, the Oscar should have gone elsewhere. While it was a hard choice, the movie just didn’t stand up to the test of time.
The awards for Matlin have been few and far between during her career. In addition to the Oscar win for Children of a Lesser God, she also won a Golden Globe for that performance. And that's about it in terms of major awards and nominations. She just hasn't been able to recreate that success.
Sigourney Weaver Should Have Won Best Actress in 1987
The reason Sigourney Weaver should have won Best Actress for Aliens was that her character grew and became this image of strength. Unfortunately, horror movies don’t usually go big at the Oscars. It happens occasionally, but the sad fact is that they are snubbed more often than not. Sigourney Weaver suffered this fate that year.
Weaver also managed to snag Oscar nominations for her work in the films Gorillas in the Mist and Working Girl, but, unfortunately, those didn't work out in the actress' favor either. She did, however, win Golden Globe awards for both of those memorable performances. But she's still never managed to clinch a coveted Oscar.
Tommy Lee Jones Won Best Supporting Actor In 1994
The Fugitive was a good movie, and Tommy Lee Jones did a pretty good job acting in it. The only issue was the other options that year for Best Supporting Actor. The nominees included Leonardo DiCaprio, Ralph Fiennes, John Malkovich, and Pete Postlethwaite. With actors like these, The Fugitive and Tommy Lee Jones won? Blasphemy.
In addition to his one Oscar win, Jones has had several other nominations. These include a nomination for Best Supporting Actor in JFK, Best Actor for In the Valley of Elah, and Best Supporting Actor in Lincoln. Any one of those would have been a better win than the one he actually got.
Leonardo DiCaprio Should Have Won Best Supporting Actor in 1994
Leo should have won Best Supporting Actor this year for What's Eating Gilbert Grape, and it should have been his first Oscar (among many wins in my mind). Critics loved the film and praised DiCaprio for his acting. In fact, I’d go as far to say that DiCaprio made the film what it is today. If there was any competition, it should have been with Ralph Fiennes, but Leo still should have won.
Fans of Leo's have for years been talking about his numerous snubs at the Oscars. These included nominations for things like Best Actor in The Wolf of Wall Street and The Aviator. However, all his Academy Award bad luck changed in 2016 when he snagged his first Oscar for Best Actor in The Revenant.
Gwyneth Paltrow Won Best Actress in 1999
Shakespeare in Love is not a fantastic movie, and Gwyneth Paltrow played the same character we’ve seen a dozen time in other romantic flicks. Giving Paltrow the Best Actress Oscar was beyond ridiculous. Although, Judi Dench did deserve her Oscar win for Best Supporting Actress.
Paltrow should really enjoy her Oscar win because it's her first and probably only one she'll ever get. These days she's too busy doing whatever it is that Goop does to worry about starring in any award-winning movies. She may have stolen someone's rightful Oscar with Shakespeare in Love, but she's likely no longer a threat to anyone in the acting world.
Susan Sarandon Should Have Won Best Actress in 1999
Is there a movie that pulls at your heartstrings more than Stepmom? Susan Sarandon played the role so well that it became one of the best films of the decade, which was hard considering how great the 90s were for movies. Despite how great it was, Susan Sarandon and the film didn’t get a single nomination. Sorry, not sorry. Susan Sarandon deserved Best Actress.
She may have missed this Oscar, but she's had one win and several nominations, and that should be enough to make any actor proud. Her win for Best Actress came in 1995 for her role in Dead Man Walking, and she received nominations for her work in movies like Thelma and Louise and Atlantic City.
George Clooney Won Best Supporting Actor in 2006
Clooney won Best Supporting Actor for Syriana. When he gave his acceptance speech, it almost seemed like a consolation prize since he hadn’t won for Best Director. As if that wasn’t bad enough, there were obviously better choices that year.
However, Clooney's accolades are not all totally undeserved. In 2013 he was part of the cast of Argo and helped them clinch the Oscar for Best Picture. And his work on films like O Brother, Where Art Thou? and The Descendants has rightfully been celebrated by the Golden Globes.
Jake Gyllenhaal Should Have Won Best Supporting Actor in 2006
Brokeback Mountain should have won Best Picture, but it also should have given Jake Gyllenhaal Best Supporting Actor. Heath Ledger, unfortunately, didn’t win because the Oscar went to Philip Seymore Hoffman for his role in Capote, which was entirely justified.
Unfortunately for Gyllenhaal, his Oscar luck is still down in the dumps. As of 2021, he's only been nominated for an Academy Award that one time. Similarly, he's only managed to get two Golden Globe nominations, and neither one of those turned into a win, either. One good film could turn all that around, though!
Alan Arkin Won Best Supporting Actor in 2007
Alan Arkin is an acting powerhouse, and he did a great job in Little Miss Sunshine as grandpa. Audiences may have wanted him for their grandpa. With that being said, Best Supporting Actor should have gone elsewhere.
In addition to this one Oscar win, Arkin had another nomination in 2012 for Best Actor in a Supporting Role for his work on the award-winning film Argo. Other than that, the Academy hasn't really seen much of Arkin, even though his career stretches back for decades. Hopefully he'll get a more well-deserved win soon.
Djimon Hounsou Should Have Won Best Supporting Actor in 2007
Blood Diamond is an underrated film that didn’t win a single Oscar. Filmed in the sweltering heat, Djimon Hounsou played a father that wanted nothing more than his son back, and audiences wanted it to happen. Most people focus on DiCaprio’s performance, which was unspeakably good, but Djimon Hounsou deserves some of the spotlight and the Oscar for Best Supporting Actor.
Unfortunately, Hounsou hasn't had much award luck in his career at all. He's got one other Oscar nomination for Best Supporting Actor in the film In America, but that didn't pan out either. Additionally, he got a Golden Globe nod for Best Actor-Drama for his work in Amistad, but that one didn't lead to a win.
Daniel Day-Lewis Won Best Actor in 2013
At this point, Daniel Day-Lewis wins an Oscar for being himself. While he is a fantastic actor, he doesn’t need to win every time he makes a movie or every time’s nominated. That isn’t to say Lincoln was bad, but other Best Actor nominees deserved it more.
Day-Lewis is no stranger to Academy Award wins, so even if he hadn't have one this one, there were others. In 1990, he won the Oscar for Best Actor thanks to his work in My Left Foot, and he won Best Actor once again in 2008 for his iconic role in There Will Be Blood.
Hugh Jackman Should Have Won Best Actor in 2013
Hugh Jackman is one of the best actors of all time, and he’s had plenty of theater experience to portray Jean Valjean in Les Misérables on the big screen. There’s no doubt that he should have won Best Actor because his singing was on point, his acting was beyond amazing, and it was one of the best films of the year.
Jackman is such a big and beloved actor that you might be surprised to hear that this was his one and only Oscar nomination so far in his career. He's already won a Grammy, a Tony, and Emmy--if he could just nab an Oscar he would officially have the coveted EGOT.