Oscars season never truly ends, and as such, it’s always a blast to look back at the history and trajectory of the most prestigious awards ceremony in the entire film industry. Throughout the history of the Academy Awards, people have perfected the art of predicting what’s going to win in any one category—but that doesn’t mean that the Academy doesn’t have a few surprises up its sleeve every now and then.
Every year, there’sat least one victory that takes even the most seasoned Oscar seer by surprise. Whether it’s an actor who was absent from most precursor awards taking home the gold, or an indie film winning in a technical category that tends to go to big blockbusters, the most shocking upsets in Academy Awards history always keep things fun and satisfyingly unpredictable.
10Bong Joon Ho — ‘Parasite’ (2019)
Won: Best Achievement in Directing
2019 in general was an exceptional year for movies, definitely one of the best of the 21st century. It saw the release of several films that could reasonably be called masterpieces, and as such, it would be hard to pick a particular one that’s the best of the year. There’s one answer to that question that’s never out of the conversation, though, and that’sParasite, a class satire by legendary South Korean filmmakerBong Joon Ho.
Some might even callParasiteone of thebest international films of the last 50 years—and if not, then at least definitely one of the most important. Its Best Picture win was historic and definitely surprising, but there’s one Oscar that it took home which was even more of a shock, and that was Bong’s win in the Best Director category. It’s not often that directors of foreign movies get nominated for Best Director—let alone win—, and withAlfonso Cuarónhaving won forRomajust a year prior, it seemed unlikely that the Academy would follow that up with yet another foreign win. Bong made it against all odds (and against frontrunnerSam Mendesfor1917), and withParasitebeing such an exceptionally directed film, it’s impossible to feel bad about it.
9’Shakespeare in Love' (1998)
Won: Best Picture
Far and away one ofthe most infamous Oscar winnersin history,Shakespeare in Lovewas definitely not worthy of its whopping seven Oscar wins, but it’s also a far better movie than many people tend to give it credit for. It’s not a masterpiece, but it’s a witty and dazzling period piece with a perfect balance between lavish visuals, tender romance, and sweet comedy.
Even still,that didn’t stop the film from beating the clear frontrunner andfarbetter filmSaving Private Ryan, one of the greatest war movies of the ’90s. Today,Shakespeare’s unlikely victory is mostly attributed to the infamously aggressive campaigning strategies of producerHarvey Weinstein, and it definintely wasn’t a Best Picture win that came entirely out of the blue; but the 1999 Oscars would definitely have aged far better ifSteven Spielberg’s masterpiece had gone home with the night’s most prestigious award.
Shakespeare in Love
8Adrien Brody — ‘The Pianist’ (2002)
Won: Best Actor in a Leading Role
Author of the most excruciatingly long Oscar speech in history,Adrien Brodyfirst walked onto the Dolby Theatre stage (and kissedHalle Berrysquare on the lips while he was at it)back in 2003 for what’s easily the best performance of his career: As the real-life Polish-Jewish pianistWładysław “Władek” Szpilmanin the harrowing WWII dramaThe Pianist.
Brody is truly larger than life in the film. One might go so far as to call his one ofthe best Oscar-winning performancesof all time, and it was definitely the best among the 5 nominees in 2003. Even still, Brody was definitely not the favorite. He won no important precursors that season, the vast majority of which instead went toDaniel Day-LewisforGangs of New YorkandJack NicholsonforAbout Schmidt. Brody’s victory was definitely a huge shocker, but a well-deserved win nonetheless.
The Pianist
7’Driving Miss Daisy' (1989)
It’s hard to callDriving Miss Daisyone of the mostinfamousBest Picture winners ever, because it’s more so one of the mostforgotten. It’s not a bad movie by any stretch (though it sure is one of theworst Best Picture recipients of the ’80s), but it’s also not extraordinary in any regard other thanMorgan FreemanandJessica Tandy’s excellent performances. It didn’t even receive a Best Director nomination, and by the time the 1990 Oscars came around, the last movie that had won Best Picture without a Director nod was 1932’sGrand Hotel.
Furthermore,Miss Daisy’s precursors run hadn’t been all that great. Instead, going into the night, it seemed thatDead Poets SocietyorBorn on the Fourth of Julywould be the ones to take the big Oscar home. The fact that theactualbest movie of 1989,Spike Lee’sDo the Right Thing, wasn’t even nominated for Best Picture was significantly controversialeven back then, and still seems like one of the Academy’s biggest mess-ups ever.
Driving Miss Daisy
6’Crash' (2004)
The question of whatthe worst Best Picture winnereveris tends to get several different answers, but the question of what the worst Best Picture winnerof modern timesis usually only gets one:Crash. The film tackles the topic of racism and prejudice in the U.S. with about as much subtlety as a rhino browsing a jewelry store, and for this, its Best Picture victory has aged like milk.
Some defendCrashas “not that bad,” but one would be hard-pressed to find anyone willing to say it’s a genuinely great film—and even more hard-pressed to find anyone who would disagree with the statement that 2005’s clear frontrunner,Brokeback Mountain, was an infinitely more deserving nominee. Instead, to the shock of absolutely everyone,Crashbecame thesecond-ever Best Picture Oscar winner that didn’t receive a Golden Globe Best Picture nomination. When the Golden Globes get it right and the Oscars don’t, you know things are in a very bizarre state.
5’Ex Machina' (2014)
Won: Best Achievement in Visual Effects
A24 has been distributing some of the best independent films in every imaginable genre for several years now, and one of their best sci-fi outings isEx Machina, the directing debut of screenwriterAlex Garland. One of the best android movies ever made, it’s an absolutely brilliant piece of philosophically-dense sci-fi that performed modestly well at the box office and phenomenally with critics as soon as it came out.
No one really expected it to receive very many Oscar nominations. A small indie genre film isn’t typically the Academy’s cup of tea.
Though it’s one ofthe most essential movies of 2014,no one really expected it to receive very many Oscar nominations. A small indie genre film isn’t typically the Academy’s cup of tea. It received a well-deserved Original Screenplay nod and an equally well-deserved Visual Effects nod, and that seemed like enough of a victory. That was until, out of absolutely nowhere, the movie beat out big-budget favorites of the stature ofMad Max: Fury RoadandStar Wars: Episode VII — The Force Awakensand took the Visual Effects Oscar home. Arguably the most shocking below-the-line Oscar victory in the awards' history, this is also one of the most satisfying underdog Oscar wins of the 21st century.
Ex Machina
4Katharine Hepburn and Barbra Streisand — ‘The Lion in Winter’ (1968) and ‘Funny Girl’ (1968), Respectively
Tied for: Best Actress in a Leading Role
Two of the most iconic and respected actresses of their generation and genres,Barbra Streisand(two-time Oscar winner) andKatharine Hepburn(four-time Oscar winner, the most Oscars a thespian has ever won) need no introduction. The two have a connection that not everyone is familiar with: They were the protagonists of the second and latest time that an acting Oscar has ended in a tie.
Streisand won forFunny Girl, one ofher most essential films, while Hepburn won forThe Lion in Winter, one ofthe best period moviesof the era. Both Streisand and Hepburn were frontrunner material, so it wouldn’t have been particularly shocking if either of them had won individually; but a tie? It’s undoubtedly one of the most gasp-worthy moments in Oscars history, as presenterIngrid Bergmanwould confirm.
The Lion in Winter
Funny Girl
3Marisa Tomei — ‘My Cousin Vinny’ (1992)
Won: Best Actress in a Supporting Role
Before she was a 3-time Oscar-nominated superstar with a role in the most profitable movie franchise in history,Marisa Tomeiwas an up-and-coming actress who broke out by starring in one ofthe best Oscar-winning comediesof the 1990s:My Cousin Vinny. A newcomer winning an Oscar for a comedic performance wasn’t exactly unprecedented back in ‘92, but it sure sounded more like fantasy than reality.
Even still, Tomei brought the Supporting Actress statuette home against all odds. She hadn’t won any significant precursors, and was nominated side-by-side with veterans of the stature ofMiranda Richardson(who won the BAFTA forDamage) andJoan Plowright(who won the Golden Globe forEnchanted April).Her Oscar win was so shocking that it birthed a conspiracy theorythat the category’s presenter,Jack Palance, had read the wrong name. This, of course, makes no sense, as presenters never read the wrong names on their cards.
My Cousin Vinny
2Marcia Gay Harden — ‘Pollock’ (2000)
The biopic genre is a rather tired one, and it has been for some time, butPollockis one of the genre’s best outings from the 2000s. Based on the life ofJackson Pollock,it’s a fascinatingly insightful look at his artistic process, anchored by a powerhouse Oscar-nominated lead performance by the greatEd Harris.
Harris wasn’t the only actor fromPollocknominated for an Oscar. There was alsoMarcia Gay Harden, who hadn’t even received so much as a nomination from the Golden Globes, BAFTA, SAG,orCritics Choice. She’s not eventhe weakest Supporting Actress winner of the 2000s—she’s actually fantastic asLee Krasner, the protagonist’s fellow artist and wife, but she hadn’t received much recognition prior to her Oscar nomination. The fact that she went on to win is still hard to believe, even for those who were there to watch her victory in 2001. It’s a historic and unprecedented win, as it’s the only time that an actor has won an Oscar without a nomination for any of the aforementioned awards.
1’Moonlight’ (2016)
The fact thatMoonlightwon Best Picture isn’t the most shocking thing in the world. Despite its small budget and indie nature, it was hugely acclaimed upon release, and won a good number of important precursors. It’showit won that’s easily the biggest shocker in the history of the Academy Awards. The mix-up that ledWarren BeattyandFaye Dunawayto announceLa La Landas the 89th Best Picture Academy Award winner is now the stuff of legend.
One ofthe most essential coming-of-age filmsof all time,Moonlightis definitely a deserving winner of Hollywood’s biggest award, which makes it all the more of a shame that its Best Picture status will forever be tied to the biggest mistake in the Academy’s history. Everyone who enjoys following the Oscars will forever remember where they were, what they were doing, and how they reacted when they watching this historic Oscar moment. It will never be forgotten.
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