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18 Totally Unexpected Oscar Wins

The most fun moments of watching the Oscars are always the surprises.

The unexpected wins from dark horses are always so much more thrilling than predictable outcomes.

It’s not that the winners were undeserving — it’s often that their wins seemed to come out of nowhere.

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With prognosticators having Oscar predictions down to a science, anything remotely surprising is a rare treat.

Here are some of the most shocking wins that left us with our jaws on the floor!

Adrien Brody Arrivals 2019 Vanity Fair Oscar Party

Adrien Brody (Best Actor In A Leading Role) in The Pianist

Brody was the only Oscar-less member of his cohort when he won for his role as Holocaust survivor Władysław Szpilman.

Up against Jack Nicholson, Nicolas Cage, Michael Caine, and Daniel Day-Lewis, Brody’s win made him the youngest Best Actor in the history of the Oscars, at age 29.

Unfortunately, his behavior is what most people remember about his win — when he kissed presenter Halle Berry non-consensually. 

Juliette Binoche (Best Actress In A Supporting Role) in The English Patient

Everyone was expecting film legend Lauren Bacall to take home the gold after landing her first(!) nomination in the Supporting Actress race for Barbra Streisand’s The Mirror Has Two Faces.

Bacall lost to Juliette Binoche, who gave a tender performance as Hana in The English Patient.

Even Binoche was shocked, and much of her acceptance speech was her reeling from the surprise.

Marshall Mathers, Jeff Bass, and Luis Resto (Best Song) for 8 Mile — “Lose Yourself”

Eminem not only has an Oscar for the hip-hop anthem from the semi-autobiographical film 8 Mile.

What’s even more impressive is that he won against industry heavyweights U2 and Paul Simon, as well as musical theatre legends John Kender and Fred Ebb.

Unfortunately, he wasn’t there to accept the award, so we were robbed of a Barbra Streisand/Eminem handoff, but her reaction upon opening the envelope is priceless.

Cher (Best Actress In A Leading Role) in Moonstruck

In a rare instance of the Academy awarding a comedic leading role, Cher surprised everyone by taking home the Oscar for Moonstruck.

Her incredibly human portrayal of the love-dazzled widow Loretta is one for the ages.

Her win is even more of a feat considering she won against Meryl Streep, Glenn Close, Holly Hunter, and Sally Kirkland — which still leaves a bitter taste in some people’s mouths.

Roberto Benigni (Best Actor In A Leading Role) in Life Is Beautiful

It was an absolutely stacked Best Actor race between Tom Hanks, Ian McKellan, Nick Nolte, Edward Norton, and Roberto Begnini.

However, it was the effervescent Italian who took home the gold, making history as the first Leading Actor to win in a non-English-speaking role.

His acceptance speech is one for the ages, his joy infectious.

Spotlight (Best Picture)

2016 was an odd year for film and for the Oscars.

Spotlight had only won one other award that evening (Best Original Screenplay) when it was announced as Best Picture, making it the first to hold that honor since The Greatest Show On Earth (1952).

Tom McCarthy’s true-life drama was a solid choice for Best Picture, but its win felt anti-climactic after the evening’s previous announcements.

Olivia Colman (Best Actress In A Leading Role) in The Favourite

What everyone thought was a race between Glenn Close and Lady Gaga ended up going to the richly deserving Olivia Colman for her role as Queen Anne in The Favourite.

Colman wasn’t a huge name stateside at the time of her win, and many considered her role in The Favourite more Supporting than Leading.

However, she has subsequently been nominated for her roles in The Father and The Lost Daughter, and she has also won two Golden Globes and an Emmy, among many other accolades.

Marcia Gay Harden (Best Actress In A Supporting Role) in Pollock

Marcia Gay Harden’s win was a surprise, having received critical praise but not much in the way of awards for her turn as Lee Krasner in the Jackson Pollock biopic.

It was Harden’s first nomination, and she won against powerhouses Judi Dench, Julie Walters, Frances McDormand, and Kate Hudson. 

Harden later received a nod for Best Supporting Actress for Mystic River (2003).

Grace Kelly (Best Actress In A Leading Role) in The Country Girl

Grace Kelly’s legacy is made up of so much glamour and tragedy — sometimes, her Oscar win for The Country Girl feels like a footnote.

She is much better remembered for her roles in Hitchcock films, as well as the Western High Noon.

Her Best Actress Oscar came at the expense of Jane Wyman, Audrey Hepburn, Dorothy Dandridge, and the heavily-favored Judy Garland (for A Star Is Born).

Beatrice Straight (Best Actress In A Supporting Role) in Network

Even Straight considered herself a “dark horse” in the running for Best Supporting Actress in 1976.

Her one scene in Network was merely ten minutes long, but she handled the role with strength, dignity, and nuance, making a lasting impression on Oscar voters.

Other than Network, Straight’s most famous role is probably that of Dr. Martha Lesh in Poltergeist (1982).

Marion Cotillard (Best Actress In A Leading Role) in La Vie En Rose

Marion Cotillard’s performance as Edith Piaf might be one of the greatest in film history.

However, she was still considered a long shot given the competition she faced that year — Cate Blanchett, Julie Christie, Laura Linney, and Elliot Page.

Cotillard’s win was one of those rare surprises that remain incredibly satisfying in retrospect, and she was also the first French-speaking Oscar winner in an acting category.

Crash (Best Picture)

Everyone thought Brokeback Mountain was a sure thing, thanks to Ang Lee taking home Best Director earlier in the ceremony.

Instead, Paul Haggis’s sprawling exploration of modern racism took the top prize.

The result remains controversial to this day, as Brokeback Mountain endures as a cultural touchstone, while Crash tends to feel dated.

Geena Davis (Best Actress In A Supporting Role) in The Accidental Tourist

Looking at her body of work, Geena Davis’s win doesn’t seem like a surprise in retrospect, but it was considered an upset at the time.

Everyone expected Sigourney Weaver to take home the gold, with Michelle Pfeiffer, Joan Cusack, and future three-time Best Actress winner Frances McDormand (her first nomination!) also in the running.

Davis’s Oscar led to a string of successes, including Beetlejuice, Thelma and Louise, and A League Of Their Own, to name a few. 

Shakespeare In Love (Best Picture)

Steven Spielberg had just won the Best Director Oscar.

Though his war epic Saving Private Ryan had swept the technical categories, it lost the evening’s biggest honor to Shakespeare In Love.

Saving Private Ryan was the favorite going in, but thanks to a vigorous campaign, John Madden’s romantic comedy made its mark on the Academy voters, even if critics consider it a slight against one of the greatest war films ever made.

Michel Hazanavicius (Best Director) for The Artist

The average American had never heard of Michel Hazanavicius, the French director behind the universally acclaimed silent film The Artist (which also won Best Picture, Best Actor, Best Costume Design, and Best Original Score).

His vision was unique, bold, and perfectly realized, but his win was still an impressive feat, considering he was up against Martin Scorsese, Alexander Payne, Woody Allen, and Terrence Malick.

The Artist was a singular, never-to-be-repeated phenomenon, and Hazanavicius’s artistry was rightfully rewarded.

Jordan Houston, Cedric Coleman, and Paul Beauregard (Best Song) for Hustle & Flow — “It’s Hard Out Here For A Pimp”

The hip-hop group known as Three 6 Mafia were unlikely winners, given that they were up against the strongly favored and universally beloved Dolly Parton.

Nonetheless, they prevailed, proving that the Academy was not as stuffy as it seemed when it came to music.

Having Queen Latifah, a rapper herself, present the award made it all the sweeter.

Rocky (Best Picture)

It was only fitting that Rocky, a celebration of the underdog, should triumph over the other classics nominated that year, including Network, All The President’s Men, and Taxi Driver. 1976 was an excellent year for film!

Sylvester Stallone was catapulted to superstardom, having gained the respect of his peers.

Rocky struck a chord with the Academy like none other, much to the shock of those who dismissed it as a schlocky sports drama. 

Anna Paquin (Best Actress In A Supporting Role) in The Piano

No one was more surprised than Paquin herself when she won the Oscar for her mesmerizing performance as Flora in Jane Campion’s The Piano.

It was her film debut, and director Jane Campion declared her a natural. Paquin had a successful career as a child actress and continues to work in film and television to this day.

Though we often see upsets in the Best Actress (Leading and Supporting) races, it feels like Michelle Yeoh and Angela Bassett are shoo-ins this year.

Will we get any surprise winners this year? We can always hope!

Who would you like to see take home the gold in 2023? What is your favorite shocking Oscar win? Tell us in the comments!

Mary Littlejohn is a staff writer for TV Fanatic. Follow her on Twitter.

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