10 Most Underwhelming Oscars Winners – Worst Academy Award Wins Over The Years

While the Academy of Motion Pictures Arts and Science can boast of the most comprehensive set of rules that determines it’s winners every year, there are still several occasions where the winners did not quite sit down well with their critics.

Much often than not, popular award shows are seen succumbing to political or fan-pressure or even popular opinions that indirectly affects whose name pops up in the final envelope on stage.



And all of that has often resulted into some pretty forgettable and unremarkable wins over the years.

Looking back, here are some of the most underwhelming winners of the Oscars in prominent categories, in contrast to those who should have won in their place.

The top 10 in no particular order:

Elton John winning over Cynthia Erivo – 2020



Elton already has had a ‘Best Original Song’ Oscar for his remarkable compositions for The Lion King, but there was nothing groundbreaking about his song “(I’m Gonna) Love Me Again” from his own biopic ‘Rocketman’ that led to his win. And to think it won over a sublime lyrical masterpiece ‘Stand Up’, created by Cynthia Erivo for the film ‘Harriet’ – a song that perfectly captured the spirit and story of Ms. Tubman.

Gwyneth Paltrow winning over Cate Blanchett – 1999

There are plenty of theories online about how Gwyneth’s victory for her film ‘Shakespeare In Love’ came to be. But we’ll not get into that. What we do know for certain, was that Cate Blanchett delivered one of the most powerful performances that year – which was beyond her years as a young and upcoming powerhouse, in Shekhar Kapoor’s Elizabeth.

Sandra Bullock winning over Gabourey Sidibe – 2010



Sandra, no doubt, is one of the most loved celebrities in Hollywood who’s adored by fans. But did that solely contribute to her Oscar win? Because as far as the actual performance was concerned in her film ‘The Blind Side’, newcomer Gabourey Sidiebe easily towered over her with a gut-wrenching act in ‘Precious’ that does not leave your head for a long time after you’ve seen it.

Geraldine Page winning over Whoopi Goldberg – 1986

Whoopi delivered – what was called by many, one of the most stunning debut film performances of all time. Her transformation in Steven Spielberg’s The Color Purple turned Celie into one of the most iconic film characters of all time. Geraldine Page, on the other hand, was fantastic in ‘A Trip To Bountiful’, but her win was more of a trophy victory for her long and illustrious career, than one for that singular performance.

Crash winning over Brokeback Mountain – 2006



Perhaps one of the most scrutinized ‘Best Picture’ winner of all time. The Paul Haggis directed multi-starrer forgettable film, has not even aged well with time, with many not even considering it a ‘good’ film, let alone something that is ‘Oscar-worthy’. And to think it won against one of the most iconic romantic dramas of all time – Brokeback Mountain, which has gone on to establish a cult status among audiences and critics alike. It was one of the most unforgivable snubs at the Academy awards.

Reese Witherspoon winning over Felicity Huffman – 2006

Reese is lovely and packs a charming on-screen presence, but ‘Walk The Line’ wasn’t exactly the kind of role that had the scope for her to win an Oscar, as she did. It was contrasted by a career-best performance by Felicity Huffman in ‘Transamerica’, whose take as a transwoman – desperately trying to fix her past in order to clear her path to undergo a gender reassignment surgery, earned her massive praise from all quarters.

Regina King winning over Rachel Weisz or Emma Stone – 2019



As marvelous as Regina King is, she had little to offer in her limited screen-time in ‘If Beale Street Could Talk’. The most applause worthy supporting female roles that year came from Yorgos Lanthimos’ period black comedy ‘The Favourite’, with Rachel Weisz and Emma Stone delivering power-packed and infectiously saucy performances. Weisz should have been the frontrunner, with Stone coming as a close second.

Cher over Glenn Close or Meryl Streep – 1988

Although Cher started her illustrious career as a singer, she has proved herself as an actress over the years. But it wasn’t her academy award winning performance in “Moonstruck” that showcases her caliber as an actress, but her fantastic, layered supporting role in ‘Silkwood’. During the year of ‘Moonstruck’, there were much better and complex performances from Glenn CLose (Fatal Attraction) and Meryl Streep (Ironweed) – which both deserved the honor a lot more than Cher’s one-dimensional simplistic act in the light-hearted rom-com.

Frances McDormand over Viola Davis or Andra Day or Carey Mulligan – 2021



Frances is one of the best actresses we have today, and she more than deserved her Oscar for her fantastic act in Three Billboards, Outside Ebbing Missouri, but when a few years later she won it again (her third overall) for her understated act in ‘Nomadland’ – it was one of the most underwhelming wins of the year. Viola Davis in Ma Rainey’s Black Bottom and Andra Day in The United States VS Billie Holiday – both delivered jaw-dropping performances in their respective films and were definitely more deserving.

Shakespeare in Love winning over Saving Private Ryan – 1999

Right alongside Crash, Shakespeare in Love ranks amongst the most forgettable ‘Best Picture’ winners in Oscar history. And to think the period-drama won it over one of the greatest war films ever made, ‘Saving Private Ryan’ – did not help either. Even ‘Life Is Beautiful’ and ‘The Thin Red Line’ were better choices in 1999 to take home the top prize.

 

Apart from these 10 ‘unholy’ and ‘unforgivable’ mistakes, here are a few more ‘Academy mishaps’ in our eyes:



Green Book winning over The Favourite
Slumdog Millionaire winning over Milk or The Reader
Holly Hunter winning over Angela Bassett
No nomination for Toni Collette for Hereditary
No nominations for Danielle Deadwyler, Naomi Ackie, Viola Davis for Till, I Wanna Dance With Somebody, The Woman King, respectively.