#23. George Clooney For Syriana
Heartthrob George Clooney is one of the highest-paid actors of this century, and it's easy to see why. Although dramas suit him best, he has starred (and nailed it, by the way) in all sorts of films, from romantic dramas to comedies, from superhero action films to thrillers.
However, for some reason, he received his only Academy Award for his dullest performance ever: that of veteran CIA agent Bob Barnes in the political drama Syriana. I'm pretty sure they gave him the award for having gained nearly 35 pounds for the role, but come on, is that all it takes to win an Oscar?
#22. Judi Dench For Shakespeare In Love
Judi Dench received 7 Academy Award nominations, but for some reason, she won only once. But do you know what the craziest part is? She won the award for her role in Shakespeare in Love, which happened to be one of her least good performances!
I'm not saying her acting was bad, but she only appeared on-screen for 7 minutes! How was she even nominated? If you ask me, the award should've been given to Lynn Redgrave for her role in Gods and Monsters. Oh well!
#21. Jared Leto For Dallas Buyers Club
Even though Dallas Buyers Club is an excellent movie, I'm sure none of you expected Jared Leto to win the Academy Award for Best Supporting Actor. His nomination actually sparked quite a controversy among the LGBTQ+ community, as it shed light on the fact that the roles of transgender characters are never given to transgender actors or actresses.
To be fair, Leto delivered a decent performance, but not as good as Michael Fassbender's in 12 Years a Slave. Also, am I the only one who thought he behaved arrogantly during the whole Oscar race?
#20. Alicia Vikander For The Danish Girl
Centered around the life of the first trans person to undergo sex reassignment surgery, The Danish Girl is one of the best LGBTQ+ films of this century. However, the critics got it all wrong. To begin with, lead actor Eddie Redmayne should've won the Oscar for Best Actor, which went to Leonardo DiCaprio.
But secondly, I have my doubts whether Alicia Vikander's portrayal of Gerda was Oscar-worthy. In my opinion, the statuette should've gone to Jennifer Jason Leigh for her role in Quentin Tarantino's The Hateful Eight.
#19. Gwyneth Paltrow For Shakespeare In Love
Is it me, or is Shakespeare in Love one of the most overrated films ever? We still can't believe that it beat Life Is Beautiful and Saving Private Ryan as Best Picture, although Gwyneth Paltrow didn't deserve an Oscar either.
Let's give the woman some credit, though, her performance was alluring and she boasted a neat British accent, but the award should've long gone to Cate Blanchett, who played Queen Elizabeth in the movie of the same name.
#18. Casey Affleck For Manchester In The Sea
In 2017, everyone thought that the Academy Award for Best Actor would go to Denzel Washington for his role in Fences, but to everyone's surprise, it was given Casey Affleck. Manchester by the Sea is one of the most heart-wrenching movies out there, I'll give you that. But I'm not sure whether Affleck's performance was Oscar material.
Casey's Academy Award sparked a major controversy months later, once it was revealed that he had recently been accused by two women for sexual harassment and physical abuse. Who would've known?
#17. Reese Witherspoon For Walk The Line
Reese Witherspoon left a mark in film history after portraying the role of college student Elle Woods in the iconic comedy film Legally Blonde. Ever since then, she has become some sort of an icon in pop culture.
I'm not implying that her portrayal of Elle was Oscar material, but neither was her role as June in the drama biopic Walk the Line. She did surprise us with her singing abilities, but her performance per se was not Oscar-worthy.
#16. Jennifer Hudson For Dreamgirls
Jennifer Hudson rose to fame after reaching the finals of the third season of American Idol, but guess what? Only 3 years later, she received her first and only Academy Award for her role in the musical-drama film Dreamgirls.
I'm not gonna lie, her performance of the film's hit song And I Am Telling You I'm Not Going was just out of this world, but should an actress win an Oscar only for one song? I don't know, I have my doubts.
#15. Jodie Foster For The Accused
Jodie Foster is one of the greatest actresses ever, and that's a fact. She received her first Academy Award nomination when she was just 14 years old after playing a teenage prostitute in Taxi Driver, though she is mostly remembered for her role as Clarice Starling in the thriller film Silence of the Lambs.
She won the Academy Award for Silence of the Lambs fair and square, and we could even say she should've won the Oscar in 1995 for her lead role in Ness. However, if you ask me, winning an Oscar for The Accused was too much. The movie wasn't that good, and her performance was average under Jodie Foster standards.
#14. Grace Kelly For The Country Girl
Not only was Grace Kelly one of the greatest Hollywood icons during the 50s and 60s, but she was also a member of the royalty, as she got married to the Prince of Monaco in 1956. Kind of like a retro version of Meghan Markle and Prince Harry!
But what you probably didn't know is that Kelly received an Academy Award she didn't really deserve. She was awarded for her role in the drama film The Country Girl, while the Oscar should've gone to the one and only Judy Garland, who nailed it in the remake of the musical A Star Is Born.
#13. Sean Penn For Mystic River
Sean Penn is one of the most talented actors of these past decades, and his portrayal of gay politician Harvey Milk proves just how gifted he is. Have you ever seen the real Milk talking in an interview? The resemblance between them both is uncanny!
But while his Academy Award for Milk couldn't have been fairer, he really didn't deserve to win a second one for Mystic River. In this 2003 crime-drama, Penn plays an ex-con whose son is kidnapped, but there's nothing special about his performance.
#12. Dustin Hoffman For Kramer Vs. Kramer
When the divorce drama Kramer Vs. Kramer hit the theaters back in 1979, the world was shaken. The thing is, divorce was still a taboo subject back in the days, and Dustin Hoffman's character was seen as an ordinary man who everyone could relate to.
However, the film doesn't hold up in 2020, because if you rewatch the film today, I'm pretty sure you'll find his character pretty sexist. Why didn't they just give the Oscar to Al Pacino? His performance in And Justice for All was way better.
#11. Jean Dujardin For The Artist
French actor Jean Dujardin became one of the first European stars to win an Academy Award for acting, after being given the statuette in 2011 for his role in the silent film The Artist.
Personally, I didn't really get the buzz around him. I didn't even get what the movie was about: Dujardin's overacting was just too irritating. Clearly, Gary Oldman deserved to win, his portrayal of George Smiley in Tinker Tailor Soldier Spy was top notch.
#10. Sally Field For Places In The Heart
Even though Sally Field is one of my favorite actresses of all time, I must admit that her performance in the 1985 drama film Places in the Heart is a bit overrated. She had rightfully won an Academy Award 5 years before after playing an Alabama trade union activist in Norma Rae, but that one Oscar was all she deserved.
To be honest, the Oscar should've gone to Vanessa Redgrave for her role in The Bostonians or to Jessica Lange for her role in Country. How did she win competing against such Hollywood giants?
#9. Eddie Redmayne For The Theory Of Everything
In the same way that Eddie Redmayne should've won an Oscar for his role in The Danish Girl but didn't, he shouldn't have won the award for The Theory of Everything, but did. What's wrong with the world?
I know that playing Stephen Hawking must be no piece of cake, but still, he wasn't that good. If you ask me, the Academy Award winner should've been Michael Keaton for Birdman.
#8. Kate Winslet For The Reader
Did you know that Kate Winslet allegedly regrets having played Rose in the drama film Titanic? She hates the fact that many people know her only for that role, and I actually get why she feels that way, as she has delivered way better performances throughout her career.
In my view, she should've won the Oscar in 2005 for her role in Eternal Sunshine of the Spotless Mind, but she earned her only Academy Award for one of her most overrated performances. Obviously, I'm talking about her role as Hanna Schmitz in the period drama film The Reader.
#7. Julia Roberts For Erin Brokovich
Julia Roberts won her only Academy Award in 2001 after playing Erin Brokovich in the drama biopic of the same name. Don't get me wrong, she nailed it, but even so, she shouldn't have won the Oscar.
Here's the deal: that same year, Hollywood legend Ellen Burstyn delivered the performance of her life after playing a 60-year-old addict in the psychological drama film Requiem for a Dream.
#6. Katharine Hepburn For Guess Who’s Coming For Dinner
Katharine Hepburn is one of the greatest legends of the Hollywood Golden Age, and her whopping 12 Academy Award nominations prove it. With a total of 4, she holds the World Record for the greatest amount of Academy Awards for acting.
But hold on… did she really deserve to win for her role in the comedy-drama Guess Who's Coming to Dinner? Even though her acting is OK, the movie hasn't aged well. With hindsight, I'd say that Faye Dunaway should've won the Oscar for her role in Bonnie and Clyde.
#5. Elizabeth Taylor For BUtterfield 8
What can we say about Elizabeth Taylor that hasn't been said already? She has received 5 Academy Award nominations throughout her career, and her Oscar-winning performance in the drama film Who's Afraid of Virginia Wolf? was truly spectacular.
However, we can't say the same about her role as Gloria in the 1960 drama movie Butterfield 8. The movie was dull, her character was dull, the screenplay was dull... We can't blame it on her, I know, but an Oscar? Seriously?
#4. Sandra Bullock For The Blind Side
I could give you at least 10 good reasons why The Blind Side didn't deserve any Academy Award nominations. To begin with, the movie was super cheesy. A rich white woman who becomes a hero for adopting a distressed black man? Come on, we've seen that thousands of times.
But most importantly, Sandra Bullock's portrayal of Texan mom Leigh Tuohy was far from believable. Personally, I think that Gabourey Sidibe should've won by a landslide for her role in Precious.
#3. Al Pacino For Scent Of A Woman
Can you believe that Hollywood icon Al Pacino won only 1 Academy Award, despite having been nominated 9 times? I know what you're thinking: it's obvious he won his only Oscar for his portrayal of Vito Corleone in The Godfather.
Well, turns out you were wrong. The actor won his only award for his role in the 1992 crime-drama film Scent of Woman. Ironically, many critics agree on the fact that this was one of his weakest performances.
#2. Christopher Waltz For Django Unchained
You must all know by now that villainous roles suit Christopher Waltz quite well. But let me ask you a question. When you saw him playing the villain in Quentin Tarantino’s Django Unchained, didn't his character ring a bell?
Of course it did, as the German actor basically played the same character in Tarantino’s previous film, Inglourious Basterds. In other words, he played the same character twice but still won the Oscar both times.
#1. John Wayne For True Grit
John Wayne is one of the greatest acting legends in film history. He's acted in 180 films (wow!) and received 2 Academy Award nominations for Best Actor. He was the number one candidate to win the award in 1950 after playing a sergeant in the action-drama Sands of Iwo Jima, but surprisingly, the Academy went for Broderick Crawford.
Nearly two decades later, the Western legend played Rooster Cogburn in the film True Grit. It was basically the same brusque, manly character he had us used to, so I don't really see the point of having given him an Oscar!