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I stopped taking award ceremonies seriously a long time ago, to be honest, because there is ultimately no right or wrong answer in regards to the finest achievements in any subjective art form, including cinema. However, I still enjoy watching the Academy Awards, and the Academy of Motion Picture Arts and Sciences does manage to surprise me with its choices from time to time, and I am certainly not the only one. See for yourself as we reminisce about the Oscar wins and losses that left movie lovers a little shocked.
Moonlight Wins Best Picture
Seeing Barry Jenkins’ acclaimed A24 movie tracing a gay Black man’s lifelong identity struggle, Moonlight, take home the top prize at the 2017 Oscars was surprising enough, given that La La Land was the frontrunner. However, the moment itself became infamous due to an incident in which presenters Warren Beatty and Faye Dunaway were handed the wrong envelope and accidentally announced the romantic musical as the victor at first.
Citizen Kane Only Takes Home Best Original Screenplay
Citizen Kane is widely celebrated as the greatest movie of all time in retrospect, but you would not know it from its low turnout at the 1942 Academy Awards, at which it was nominated in nine categories but only earned Best Original Screenplay. Its mixed reception (and reported boos at the Oscar ceremony, according to Collider) were the result of a smear campaign ordered by William Randolph Hearst, who is said to have inspired star, director, and co-writer Orson Welles’ drama about a megalomaniacal media tycoon.
Mikey Madison Wins Best Actress Over Demi Moore
After Demi Moore‘s tragic performance in the instant classic horror movie, The Substance earned her the Best Lead Actress award for nearly every other ceremony prior, experts were convinced the Hollywood veteran would win the category at the 2025 Academy Awards. Thus, it was shocking to see then-25-year-old up-and-comer Mikey Madison take home the gold for her performance in the title role of Anora.
Alan Arkin Wins Best Supporting Actor Over Eddie Murphy
It seemed like Eddie Murphy was a lock to be the first Saturday Night Live star to win an Oscar for his supporting role in the 2006 musical Dreamgirls. Yet, it ended up going to Alan Arkin for Little Miss Sunshine. With all due respect to the late actor’s wonderful performance in the beloved dramedy, many still believe Murphy deserved the award and even blame his ill-received comedy Norbit from the same year for hurting his chances.
Shakespeare In Love Wins Best Picture Over Saving Private Ryan
Director Steven Spielberg‘s powerful war movie, Saving Private Ryan, was the frontrunner to win Best Picture at the 1999 Oscars. While Spielberg took home his second directorial prize, the movie lost to Shakespeare in Love. A retrospective by Den of Geek claims the romantic period drama’s wins – also including Best Actress, Supporting Actress, Original Screenplay, and Score – were the result of the producers’ strategic campaigning, supposedly altering the Academy’s decision-making process forever.
Marisa Tomei Wins Best Supporting Actress
Marisa Tomei beat esteemed Hollywood veterans Vanessa Redgrave and Miranda Richardson in the 1993 Oscars’ Best Supporting Actress category for her breakthrough role as Mona Lisa Vito in My Cousin Vinny. Her win for the otherwise hilarious and charming performance was such a surprise that many speculated presenter Jack Palance had accidentally read the wrong name, and the Academy just let her keep it.
Barbra Streisand And Katharine Hepburn Tie For Best Actress
The third time that an Oscar vote ended in a tie occurred in 1968 when both Barbra Streisand and Katharine Hepburn earned Best Actress. Streisand won for her performance in Funny Girl, and Hepburn’s role in The Lion in Winter also impressed an equal number of Academy voters.
Suicide Squad Wins Best Makeup And Hairstyling
In 2017, director David Ayer‘s Suicide Squad took home the award for Best Makeup and Hairstyling for the way it transformed its actors into bizarre DC supervillains. Setting aside the comic book movie’s largely negative reception, the film’s victory over the eye-popping makeup effects in Star Trek Beyond was shocking.
Anora Wins Best Picture
The story of a young “lady of the night” and her ill-fated marriage to a rich, Russian twenty-something became the 2025 Oscars frontrunner late in the game, which made its Best Picture victory over safer bets like The Brutalist quite a surprise. Anora also made history when Sean Baker earned Oscars for directing, writing, and editing in the same night.
Anthony Hopkins Wins Best Actor Over Chadwick Boseman
There was so much confidence in the chance that Chadwick Boseman would win a posthumous Best Actor Oscar for Ma Rainey’s Black Bottom that the category was saved for the end of the 2021 telecast. Instead, it went to The Father‘s Anthony Hopkins, who was not even present at the ceremony, which left a bit of a sour taste in viewers’ mouths.
Crash Wins Best Picture Over Brokeback Mountain
The world was absolutely convinced that director Ang Lee’s buzzy gay love story, Brokeback Mountain, would take home the top prize come Oscar night in 2006. Instead, the winner was writer and director Paul Haggis’ examination of modern prejudice, Crash, much to the surprise and even dismay of many critics and audiences at the time and for years to come.
Marcia Gay Harden Wins Best Supporting Actress
In 2001, Marcia Gay Harden’s portrayal of Lee Krasner in Pollock earned her both her first Academy Award nomination and win, but that is not what made it such a remarkable achievement. The actor had not won a single accolade for the performance before beating the likes of Kate Hudson and Frances McDormand in Almost Famous on Oscar night.
Eddie Redmayne Wins Best Actor Over Michael Keaton
Michael Keaton‘s performance in 2015’s Best Picture Oscar winner, Birdman or (The Unexpected Virtue of Ignorance), was poised to earn him the Best Actor award that night. Instead, the former Batman actor lost to Eddie Redmayne, whose portrayal of Stephen Hawking in The Theory of Everything is retrospectively not held in as high regard.
Rocky Wins Best Picture
Rocky, starring writer Sylvester Stallone as the titular aspiring boxer, is a great underdog story, and the same could be said about its jog to the Oscars stage in 1977. The film won three Oscars, including Best Picture over strong contenders Taxi Driver, Network, Bound for Glory, and All the President’s Men.
Bob Fosse Wins Best Director Over Francis Ford Coppola
It is rare to see a movie win the Best Picture Oscar without seeing its director also take home a statuette. However, that is what happened in 1973 when Francis Ford Coppola‘s The Godfather won the top prize, but best director went to Bob Fosse for Cabaret.
Three 6 Mafia Win Best Original Song
When Three 6 Mafia won the 2006 Oscar for Best Original Song for Hustle & Flow‘s “It’s Hard Out Here for a Pimp,” it was not the first time that a hip-hop artist earned the award, as Eminem had won for “Lose Yourself” from 8 Mile only a few years earlier. Still, a rap song earning such an accolade was still considered a rarity, and adding the fact that Dolly Parton (for Transamerica‘s “Travelin’ Through”) and Kathleen “Bird” York (for “In the Deep” from Crash) were the competition, it was an unexpected victory.
Driving Miss Daisy Wins Best Picture
The competition between Driving Miss Daisy and its fellow Best Picture Oscar nominees (Born on the Fourth of July, Dead Poets Society, Field of Dreams, and My Left Foot) was not exactly fierce. What made its victory – in addition to wins for Best Actress (Jessica Tandy), Adapted Screenplay, and Makeup – a surprise was that its director, Bruce Beresford, was not even nominated.
Beatrice Straight Win Best Supporting Actress
Beatrice Straight appears in 1976’s Network, in which she, as Louise, tearfully and angrily reacts to her husband, Max Schumacher (William Holden), revealing he has been having an affair. Her powerhouse performance in the five-minute sequence was enough to convince the Academy that she deserved the Best Supporting Actress Oscar.
Adrien Brody Wins Best Actor For The Pianist
Adrien Brody won his first Academy Award for leading the 2002 World War II-era biopic, The Pianist, making him the youngest person to win in the Best Actor category at 29 years old. Making matters even more surprising, he was going up against esteemed Oscar winners Jack Nicholson (About Schmidt), Michael Caine (The Quiet American), Nicolas Cage (Adaptation), and Daniel Day-Lewis (Gangs of New York), the latter of whom was the frontrunner.
Olivia Colman Wins Best Actress Over Glenn Close
In 2019, Glenn Close received her seventh Academy Award nomination for her role in The Wife, which had already earned the actor multiple accolades, convincing many that this would finally be the year she goes home with an Oscar. Instead, her losing streak would continue when the Best Actress winner turned out to be Olivia Colman for her wonderful performance in Yorgos Lanthimos’ absurdist period satire, The Favourite.
Dances With Wolves Wins Best Picture Over Goodfellas
Kevin Costner made his directorial debut with the Civil War-era, Western movie classic, Dances with Wolves, which took home Best Picture. While it was an undeniably impressive achievement for the actor and filmmaker, who also starred in the drama, it was a bittersweet occasion as esteemed veteran Martin Scorsese’s acclaimed crime thriller, Goodfellas, only took home a statuette that night for Joe Pesci’s supporting performance.
Grace Kelly Wins Best Actress Over Judy Garland
At the 1955 Academy Awards, the frontrunner in the Best Actress category was the legendary Judy Garland for the first remake of A Star is Born. Thus, it came as quite a shock to see Grace Kelly winning the Oscar for her role in The Country Girl as the wife of an alcoholic actor desperately seeking a comeback.
Parasite Wins Best Picture
By Oscar night 2020, it was nearly impossible to tell which of the many Best Picture frontrunners, from Quentin Tarantino’s Once Upon a Time in Hollywood to Sam Mendes’ 1917, would prove to be the victor. Yet, nobody anticipated that Bong Joon Ho’s South Korean thriller Parasite, which had also won Best International Feature that night, would take home the top prize, becoming the first foreign-language film to do so.
Art Carney Wins Best Actor Over Al Pacino
Al Pacino’s two-decade losing streak would end in 1993 when he won the Best Actor Oscar for Scent of a Woman, which was also his eighth nomination. One of the most surprising instances in which he lost was in 1975, when his performance as Michael Corleone in The Godfather Part II was expected to be the winner until he was bested by Art Carney in the road trip comedy Harry and Tonto.
Green Book Wins Best Picture
While it was well-received upon release, many critics and experts feared the idea of a simple and safe drama like Green Book winning Best Picture at the 2019 Oscars against more esteemed and refreshingly ambitious films like Roma, The Favourite, and A Star is Born. Of course, that turned out to be exactly what happened.
Kevin Costner Wins Best Director Over Martin Scorsese
Not only did Kevin Costner’s Dances with Wolves earn the top prize at the 1991 Oscars, but the first-time filmmaker was also awarded Best Director. Also nominated in that category that year, and for the third time, for his expertly crafted mafia drama, Goodfellas, was Martin Scorsese, who would not take home the award until 16 years later for The Departed.
Anna Paquin Wins Best Supporting Actress
The Best Supporting Actress Oscar nominees in 1994 included Rosie Perez for Fearless, Winona Ryder for The Age of Innocence, Emma Thompson for In the Name of the Father, and Holly Hunter for The Firm (the latter two of whom were nominated for two acting categories the same year). However, the winner was The Piano‘s Anna Paquin, who, at just 11 years old, became one of the youngest people to receive an Academy Award.
The Color Purple Wins Nothing
You can usually count on the film with the most Oscar nominations to go home with at least one statuette, but that was not quite the case in 1986. The Color Purple was tied with Out of Africa with 11 nominations, and while Sydney Pollack’s romantic drama earned seven awards, including Best Picture, director Steven Spielberg’s adaptation of Alice Walker’s celebrated novel left completely empty-handed.
Joel Grey Wins Best Supporting Actor
Three of the Best Supporting Actor nominees at the 1973 Academy Awards were from The Godfather (namely Al Pacino, Robert Duvall, and James Caan), and none of them ended up taking home an Oscar. The winner, instead, was Joel Grey, for his performance as “Master of Ceremonies” in Cabaret.
Juliette Binoche Best Actress Over Lauren Bacall
Screen legend Lauren Bacall earned her sole Oscar nomination in 1997 for The Mirror Has Two Faces. However, the Best Actress winner that night was first-time nominee Juliette Binoche for her performance in The English Patient, which also won Best Picture.
The Greatest Show On Earth Wins Best Picture
Steven Spielberg has cited director Cecil B. DeMille’s The Greatest Show on Earth as an early influence on his interest in filmmaking. However, most modern audiences and critics are baffled by the fact that this drama, taking place at the circus, was voted Best Picture at the 1953 Academy Awards.
Robert Donat Wins Best Actor
In a Best Actor Oscar category that also included Clark Gable in Gone With the Wind and Jimmy Stewart in Mr. Smith Goes to Washington, the winner turned out to be Robert Donat for Goodbye, Mr. Chips, surprisingly.