Top 10 WORST Acting Oscar Wins of ALL TIME 

To me it will always be Gwyneth Paltrow for Shakespeare in Love. She honestly has never impressed me with any of her acting. She bores me in everything she does and the Oscar should have gone to Cate for Elizabeth

Ralph Fiennes losing to Tommy Lee Jones is the one that bothers me the most. Ralph Fiennes was absolutely terrifying in Schindlers List and Tommy Lee Jones was playing… a grizzled cop who was essentially… Tommy Lee Jones. It was weird.

Gwenath Paltrow in Shakespeare in Love really pissed me off.

Ted Levine not being even nominated for “Silence of the Lambs” as criminal. He was terrifying and creepy… but Jody and Anthony got nominated and I think won? Director Jonathan Demmy recognized Levine in his best director win Oscar speech.

I expected Gwyneth Paltrow on Place 1. Her winning over Cate Blanchett and Fernanda Montenegro is still mindblowing.

I’m still surprised that Glenn Close has not won an Oscar. She’s been nominated, but never won.

For Asian-American actress Anna Mae Wong, mainly typecast as the villain at the time, her absolute worst Hollywood experience was losing the part of O-Lan in "The Good Earth" (1935) to Luise Rainer. Her filmed audition reportedly brought casting agents to tears, but in 1935 Hollywood, casting an Asian Actress in the lead opposite white leading Man Paul Muni, simply wasn't going to happen; they offered her the part of Lotus instead, which she made clear she would audition for but would not play, it being another stereotypical Asian role. This was when Anna pretty much gave up on Hollywood & herself, becoming a broken Alcoholic, just working to pay the bills, until her death in 1961 from a heart attack. This is what makes Luise Rainer's Oscar win for this role truly galling, as well as tragic.

Aside from Gwyneth Paltrow's win in Shakespeare in Love I thought Reese Witherspoon 's win in I Walk the Line was weak. It didn't do anything for me.

Too often Oscar goes to someone for career achievements, not a specific role.

The no. 1 worst Oscar win of all time is Gwyneth Paltrow for Shakespeare in Love. Her flat performance aside, that her character was disguising as a male and she supposedly had everyone fooled was laughable. But the real Shakespearean tragedy is how she defeated Cate Blanchett.

John Cazale: Starred in a total of five films, every one of them a hard-hitting drama nominated for best picture. Never nominated for an acting award. Gwyneth Paltrow: "lifestyle entrepreneur" who starred in a dull comedy fluff about Shakespeare. Won an Oscar the very first time she was nominated for one.

I always think Kim Basinger didn’t deserve the Oscar for L.A. Confidential. The film is good, but her performance to me is merely so so.

A week before my grandma went on hospice and died and took her to go see Precious. I wanted to see it and thought she would fall asleep. She cried her throughout the film and when Monique was violent, grandma signaled to me Gabrielle was her. After the movie grandma told me the movie was her story. My grandma was a tiny little white lady, but Monique and Gabrielle's performance was transcending. That last week of grandma's life I thanked her for not continuing the cycle of abuse and being a wonderful mom to my mom who was wonderful to me. She also told us what we all suspected that her father raped her, but she insisted she did nothing wrong and was a good child. We told her she did nothing wrong. Then she died. I really think she was holding onto some sort of closure and Precious gave it to her. She spent her whole life feeling worthless because she didn't have a career and money, but really she was so strong for leaving her toxic family. Anyways, I totally forget Sandra's character leaving thr cinema.

It's also surprising how Ralph Fiennes in Schlinder's List managed to lose the Best Supporting Actor Oscar to Tommy Lee Jones in Fugitive.

I stopped caring about who won the Oscars a long time ago.

Has anyone done a "vindicated by time" list? As in, people thought they shouldn't win, but on revisiting, their performance is better. I'm thinking of Marisa Tomei in My Cousin Vinny. She was great but everyone thought it was a mistake!

For me it is Edward Norton Jr. not winning the supporting actor award for Primal Fear. He lost to Cuba Gooding Jr. for Jerry McGuire. I do not understand that at all.

Ellen Burstyn in Requiem For A Dream lost to Julia Roberts Ellen’s performance was brutally incredible, transformative. It was a difficult movie to watch as all the main characters suffered from addiction. But it was the best performance of the year! This was one was one the worst snubs!!

I think the Academy selection, nomination, and election is a very political process. There's a lot of lobbying behind the scenes, and persuading Academy members how to vote. Half the time (as I understand it), the members haven't even seen the films they're voting for.

Val Kilmer should have been nominated and won a supporting actor award for playing Doc Holiday in “Tombstone”. He was robbed. Just shows how the Oscars is pure politics.

I would add Gywneth Paltrow. This was very one-dimensional and i was shocked that she won over Cate. I also thought it was a travesty that Joseph Fiennes wasn't even nominated for Shakespeare in Love or Elizabeth.

I totally agree. How can you compare Gwenith Paltrow's ditzy,one-dimensional performance to Cate Blanchett's deep portrayal of Elizabeth. You just have to look at their body of work since.

So funny of you to think the Oscars are about acting.

Everyone is going to kill me for saying this but I am still in shock that Michelle Yeoh won for that multiverse gimmick of a film over Cate Blanchett in Tar - Cate’s performance wasn’t just the best that year, it was one of the greatest in the history of cinema.

Willem Dafoe's performance as Van Gogh in "At Eternity's Gate" was hugely underrated. Van Gogh's been portrayed many times, but Dafoe's portrayal was so unflinching, so real and heartfelt. He wasn't playing him as a "great artist", he was portraying a deeply troubled, ill, misunderstood man who saw the World in a breath-takingly beautiful way.

Gwyneth Paltrow for shakespear in love was a total scandal

The flaw is believing awards are based solely on merit and not about the marketing. This unfortunately, more often than not, creates a chasm between who wins and who ought to have won.

It seems like actors often win for playing real people over actors who play fictional characters.

Gwyneth Paltrow not being the no.1 is a crime. Like come on, for every list of "undeserving" wins, she should always be on top.

John Hurt not winning for "The Elephant Man" was the greatest travesty in Oscar history.

Edward Norton should have won for Primal Fear.

I think even Sandra agreed she didn't really deserve to win. Her reaction and acceptance speech kind of gave me that feeling. It was most likely a "thanks for all your hard work and for bringing attention to this story". The movie is somewhat controversial - "white saviour", recent revelations that it was not truthful and they shafted the guy and took half his money, or something like that. It would never make it to the awards circuit nowadays.

Can we get an “elusive Oscar” video for Viggo Mortensen?? Incredible actor.

Literally how Gwyneth Paltrow wasn’t mentioned for Shakespeare in Love is crazy.

I find that people who claim that Ralph Fiennes should've won for "Schindler's List" and those who say that Val Kilmer should've been nominated and won for "Tombstone" generally aren't aware that they would've been competing against each other. Alongside Fiennes, the other nominees for Best Supporting Actor in the 66th Academy Awards were: Tommy Lee Jones in "The Fugitive" John Malkovich in "In the Line of Fire" Leonardo DiCaprio in "What's Eating Gilbert Grape" Pete Postlethwaite in "In the Name of the Father" Other snubs include Ben Kingsley in "Schindler's List"; Sean Penn in "Carlito's Way"; Gary Oldman, Christopher Walken, & Dennis Hopper in "True Romance"; etc...

I am still not happy that Russel Crowe did NOT win for best actor for A Beautiful Mind. He absolutely should have won.

- The main reason why Barbara Stanwick never won an Oscar it's because she was a freelancer and didn't have the power of a studio to push a big campaign for her. (Luise Rainer's back-to-back wins had MGM written all over them) - Helen Hayes is the only actor to get an Oscar for her first film and for her last. - Anna May Wong, the most famous Asian-American actress of the 1930s, campaigned hard for the lead role in The Good Earth, but since Paul Muni was cast as the male lead and the Hayes Code forbidded onscreen interracial couples, Wong couldn't play the lead role (even though she was the real Asian). If that stupid code didn't exist, we probably could have seen the first Asian actress getting an Oscar.

Elizabeth Taylor stated in many interviews that she knew it was a sympathy vote . And that she hated her performance in that .

I read an article where Elizabeth Taylor said she'd won one Oscar for her tracheotomy. I'm in my 70s so old enough to have read articles from the 1960s when they came out.

How could Gwenyth Paltrow be left off the list? She’s horrible in every role she plays. And to win for her worst role??

It always upset me too that Rami Malek won Best Actor for Bohemian Rhapsody, but Taron Egerton wasn’t even nominated for Rocket Man. Not only did he do his own singing, but he also gave a way better performance in my opinion.

The most interesting about Elizabeth Taylor’s win on Butterfield 8 is that she kind of cringed the fact that she won an Oscar for that movie.

For me Burgess Meredith in Rocky was a much more memorable performance than Jason Robards in All The President's Men

Jennifer Lawrence in Silver Linnings Playbook. I was incredibly upset of her win on that. Completely undeserved

These lists are always personal and must be respected. I, personally, think that Gwyneth didn't deserve to win over Cate Blanchett and Fernanda Montenegro (but I haver my bias, because I'm from Brazil 😬). I often see people mentioning that Ellen Burstyn deserved the Oscar in 2001 for Requiem for a Dream, over Julia Roberts.

I am so glad you said Gabourey Sidibe should have won Best Actress over Sandra Bullock, because she absolutely should have!!! I was so mad when she lost! I wanted her and Monique to have their moment together!! Totally agree!

The thing to keep in mind is thst the Oscars are an industry award. The 6K nembers of the Academy are oe ones who vote. The award is NOT about the quality of the acting or the film. It's about who in the industry can persuade the members to vote for a particular actor or film. Also, sometimes an actor will get an award as compensation for a not getting one for a previous performance.

And what about the Oscar that was deprived from Bette Davis for Baby Jane, because scheming Joan Crawford her co-star campaigned to the Academy for Bette not to get it. In the past Joan stole 2 of Bette's boyfriends, one of the guys was handsome actor Franchot Tone who Bette once described as her soul mate.

Gwyneth Paltrow not being in the top five of your list is absolutely criminal. I mean, between her and Blanchett? Come on, Brian lol

Peter O‘Toole should have won an Oscar three or four times!!!!

I always thought Sally Field should have won best supporting actress for Lincoln instead of Anne Hathaway for Les Miserables . Her argument with Abe to save her oldest son from enlisting was soul wrenching

I think general consensus is Gwyneth Paltrow Shakespeare in Love is worst wrongly award given. The one that just sticks in my craw is Ralph Fiennes. Seriously!! How could he not win for Schindler’s list?!? That was a travesty!! Almost on the scale of the film’s content.

How about Al Pacino in Scent of a Woman? That was a legacy win, for sure. "Hoo-ah!" Ugh, after all the incredible characters of the '70's and '80's, they honor him for chewing up the scenery - "Hoo-ah!" He beat Eastwood in Unforgiven; Denzel in "Malcolm X"; Stephen Rea in "The Crying Game"; and RDJ in "Chaplin". The Academy is so messed up.

There are LOADS more … Ellen Burstyn to lose to Julia Roberts’s average performance? Judy Garland to lose to Grace Kelly.. really? Glenn Close to lose with Fatal Attraction to Cher? Oh please! Gweneth Paltrow to win over Fernanda Montenegro and Cate Blanchett… and so on…

I was always sad when Sasha Baron Cohen dropped out of playing Freddie Mercury because I think he would have been amazing. But he wanted the movie to be darker, and go deeper into the addictions Mercury had. He was also working to get Scorsese on board to direct. But other members of Queen had veto over the script and how things were portrayed and they didn’t want to get into the darker aspects of his life. So eventually Cohen left the project.

Shirley MacLaine was wonderful in The Apartment. Liz Taylor was just so-so in Butterfield 8. Shirley got robbed.

Paltrow's win will never make sense to me, Fernanda Montenegro was amazing in Central Station!

Your reasoning on Louise Reiner is specious. Whatever she chose to do after winning the Oscar 2 years in a row is irrelevant to the quality of her work. If you made your argument on the basis that the other actor you mentioned gave a better performance that would at least make sense. So winning multiple awards should not be allowed. So will we take away Katherine Hepburn's "extra" Oscars? Or Jack Nicholson's?

Mary Pickford’s performance in a 95 year old movie is a very odd choice at No. 2. I don’t think you are in a position to exercise proper judgement based on watching a part of a film that also requires a historically-based sensitivity to the performance standards of the period. At the very least, you would need to have watched a selection of the other nominated films in an effort to determine the acting conventions that prevailed, especially at a time when the transition from silent to sound film was sending waves through the industry.

I'm still sore about Julia Roberts in Erin Brockovich winning over Ellen Burstyn in Requiem For A Dream...

Peter O'Toole and Richard Burton should have win an Oscar!

In line with what you were saying about Fontaine's win- Ginger Roger's Best Actress win at the 1941 Oscar's should be on this list. The nominees were: Ginger Rogers - Kitty Foyle as Kitty Foyle Bette Davis - The Letter as Leslie Crosbie Joan Fontaine - Rebecca as the second Mrs de Winter Katharine Hepburn - The Philadelphia Story as Tracy Samantha Lord Martha Scott - Our Town as Emily Webb Fonatine gave a career best and defining performance, Hepburn made a triumphant return after being labeled box office poison, and Davis is sensational. The three of them most definitely deserved the win over Rogers, who gave a good, but not particularly special performance.

Gwineth Paltrow for Shakespeare in Love ... i can't handle this

One Oscar win that I DEFINITELY did not agree with is Michael Caine for "Cider House Rules". That Best Supporting Oscar should have gone to Michael Clark Duncan for "The Green Mile". That one still eats at me.

Jamie Lee Curtis winning for Everything Everywhere All At Once was one of the most obvious legacy wins vs performance wins I've seen. Everyone was baffled by it. Edit: Man, you guys are DEFENSIVE about a fairly decent but not particularly notable performance, LOL.

Tell me how Rami Malek got an Oscar for a movie he lip synced and Taaron Egerton didn’t get a nod even though he sang all the music???

Ginger Rogers beating Joan Fontaine in "Rebecca" and Katherine Hepburn in "The Philadelphia Story" is the worst ever.

Top three that you missed: 1. Art Carney for Harry & Tonto 2. Reese Witherspoon for Walk the Line 3. Gwyneth Paltrow for Shakespeare in Love

Al Pacino deserved Oscar's for a lot of other movies, but there's no way he should have won over Denzel Washington in Malcolm X.

Amazing list and commentary. Thank you...subscribing

Great channel. Just found it and love the analysis. I’ll be subscribing.

The ones that bug me the most are when the old veteran who hasn't won before, gets recognition late in their career because they've come back and they win because of their career's work or because "wouldn't it be great if they won", regardless of how good the actual performance is. Even though they have an Honorary Oscar that they could give to them for their career. It defeats the idea of a competitive win and means that people who are worthy are themselves overlooked, only to be give "their turn" to win later in their career.

All good picks, but two of the worst were Grace Kelly over Judy Garland’s stellar performance in “A Star is Born”, and the incredibly irritating Judy Holiday over both Gloria Swanson (“Sunset Boulevard”) AND Bette Davis (“All About Eve”).

I do like Sandra Bullock, and I hope she earns an Oscar one day, but she didnt deserve it for Blind Side.

It's all about who has to win for the year to make it Fair And diverse

I agree with all your choices. I also think Helen Hunt’s win for As Good As It Gets was undeserved. It should have been Judi Dench for Mrs. Brown. And then Dench winning Supporting Actress for Shakespeare in Love was clearly to make up for that slight.

As was often said by Robert Patrick (the playwright, not the actor) regarding Oscars, "The award is for the BEST acting, not the MOST acting."

Gwyneth Paltrow not being on this list is absolutely criminal

I would add Denzel Washington in Training Day in 2001. He was good but Russel Crowe in A Beautiful Mind should have won. I think Washington should have won for his performance in Man on Fire on 2004. Most considered it a critical flop but I thought it was really good and Washington's performance was exceptional. Also, Cher for Moonstruck. It should have been maybe Glenn Close for Fatal Attraction but although good, Cher's performance was not her best. She should have probably won in 1985 for Mask. It was her best performance but the category was really tough that year. And lest we not forget Shakespeare in Love. Neither Gwyneth Paltrow nor Judi Dench should have won for their performances in that movie. Paltrow was not that good and Dench was barely in the film. There are so many others and now the Oscars are just a joke.

Elizabeth Taylor also benefited from the make up Oscar. She has been screwed out of an award for Cat on a Hot Tin Roof, because the public believed she had destroyed Debbie Reynolds and Eddie Fisher’s marriage.

Now we know “The Blindside” is 100% fiction and Sandra most likely regrets being involved.

You got the part about Elizabeth Taylor partly right. She did get ill and almost died. It was during the filming of Cleopatra. She had to undergo a trac on her troat to save her life. You can see the scar in that film. Elizabeth said in an interview or one of her books that she never liked Butterfield 8 and knew she didn't deserve the Oscar. It was a sympathy vote that the Oscars are known for doing more and more these days. Unfortunately.

Jane Fonda in Coming Home. She opposed the Vietnam War but had no problem getting paid for acting in a folm that had it as subject matter.

Jack Nicholson winning best actor for As Good As It Gets in 1998 belongs on this list. He mailed in his performance, doing his Jack Nicholson personaa, and he was _badly_ miscast (much too old, even by Hollywood standards) against Helen Hunt, but (as we see several times on this list), he got the Best Actor award as a kind of "Lifetime Achievement" Oscar. He has given some wonderful performances (and won Oscars for some of them), but this was SO not one of them. Either Robert Duvall (for the Apostle) or Matt Damon (for Good Will Hunting) were far more deserving.

Julia Roberts (Erin Brokovich) winning over Ellen Burstyn (Requiem for a Dream)

Bohemian Rhapsody - when an extended SNL sketch gets nominated

pretty big name actress makes herself ugly for a film=oscar nomination

I was patiently waiting for you to mention Jamie Lee Curtis winning for 'Everything Everywhere All at Once'. 😬

Joan Fontaine winning for an Alfred Hitchcock film a year after Rebecca is a makeup award for not winning the year before…BUT it was also a big deal because of the “sibling rivalry” between Fontaine & Olivia de Havilland (for Hold Back the Dawn). Stanwyck was the only nominee whose film wasn’t up for best picture, so she had that going against her. So, yeah, it was a makeup award & a decisive factor in the “sibling rivalry”.

Julia Robert's winning for Erin Brockovich in 2000 over Ellen Burstyns amazing performance in Requium for a dream!! And not even acknowledging Toni Collettes performance in Hereditary was ridiculous

Besides an obvious “winner” in this category - Gwyneth Paltrow - I’d add Jennifer Lawrence. As much as I love JLaw, she should’ve gotten her Oscar for mother! not SLP

The Oscars get it wrong more often than not. Just one example--Jonah Hill, a pretty good, occasionally memorable actor, has been nominated twice for an Academy Award. Harry Dean Stanton, one of the greatest actors of all time with a decades-long career that included performances in classic films and his towering leading role in Paris, Texas--never nominated. Not even once.

Julia Roberts for Erin Brokovich over Ellen Burstyn in Requiem for a Dream was a huge upset

For me, the biggest farce at the Oscars and the whole reason I never watched again was the year Bette Midler lost for her portrayal of Janis Joplin in the Rose to Sally Field in Norma Rae. I hated Norma Rae and Sally didn’t hold a candle to Bette. Of course here we are all these years later and I can’t stand anything that comes out of Midler’s mouth due to everything having to be political.

There's no question Pickford was way below her par in Coquette, but it doesn't follow that she then had to "buy" an Oscar. She got an oscar for her clout in the industry and the strength of her acting over the length of her career, which pretty much defines a "legacy win".

One “Oscar Winning” performance that has always bothered me was Roberto Benigni for Life is Beautiful. Great movie, but he basically plays the same character in every movie. I guess he also should had been nominated for Son of the Pink Panther too. Edward Norton for American History X was the clear winner that year.

How Gwyneth won over Cate still baffles me. I feel it was a sympathy vote to Gwen due to the loss of her father.

LOVE the Karen Black shoutout, she has never got the level of respect I think she deserves, especially for her Five Easy Pieces performance. Justice for Karen Black !!

Tommy Lee Jones winning for "The Fugitive" over Leonardo De Caprio's performance as Arnie in "What is Eating Gilbert Grape."

Your comment on Rami Malek reminded me of Cate Blanchett winning the Oscar for the role of Katherine Hepburn in Aviator. Same thing here, she is trying far too hard to make an impression. Like so often, you get the Oscar simply for playing a famous person.