To win an Oscar is perhaps the greatest honor that any film can possibly aspire to. To win multiple Oscars is an achievement so great that most filmmakers throughout the Academy’s existence have only ever dreamed of it. To win multiple Oscars and then go on to win Best Picture, the single biggest and most prestigious award that the film industry has to offer, is nothing short of transcendental.
However, there can only be one Best Picture winner; and, as such, the vast majority of films nominated during any given year will go home without the big prize—even if they’ve won many other Oscars. There have been only a few noteworthy Best Picture nominees throughout history that have managed to win five or more Academy Awards—already a huge feat in itself—, yet still failed to get the biggest award of the night.
12
‘Hugo’ (2011)
Won: Cinematography, Art Direction, Sound Editing, Sound Mixing, and Visual Effects
Martin Scorsese is one of the most legendary filmmakers in history, and many would go so far as to call him the greatest currently-working director. However, there’s a long track record of proof that the Academy loves to nominate his movies, but not actually give them all that many Oscars. That’s not always the case, however, and Hugo—one of the best family movies of the 2010s—is proof of that.
This family adventure drama is tied with The Aviator as the Martin Scorsese film with the most Oscar victories, with five. They were all well-deserved, too. In the end, however, the film lost Best Picture to one of the most controversial recipients in the award’s history: Michel Hazanavicius‘ French-Belgian silent dramedy The Artist, which was the clear Best Picture frontrunner throughout most of the 2011-12 season. Did Hugo ever really stand a chance at the top prize? Not really, but its tie with The Artist as the biggest winner of the 84th Academy Awards has to count for something.
11
‘The Aviator’ (2004)
Won: Supporting Actress (Cate Blanchett), Cinematography, Art Direction, Film Editing, and Costume Design
The other biggest Oscar winner in Scorsese’s catalog, The Aviator is a spectacular biopic about Howard Hughes that has aged like fine wine. It’s one of the best Oscar-winning biopics of all time, and its status as the winner of the most Oscars at the 77th Academy Awards (an impressive five) is nothing to scoff it. For a good portion of the season, in fact, it was a strong frontrunner for Best Picture.
However, The Aviator‘s biggest competition was Clint Eastwood‘s Million Dollar Baby; and by the time the movie won both the DGA and PGA, it seemed like the deal was sealed. Indeed, Eastwood’s film went on to win Best Picture and three other Oscars. Even still, time has been kind to The Aviator. In particular, Cate Blanchett‘s Supporting Actress win for playing Katharine Hepburn is one of the best-liked of the 2000s, and it marks the only time that an actor has won an Oscar for playing a fellow Oscar winner.
10
‘Who’s Afraid of Virginia Woolf?’ (1966)
Won: Actress (Elizabeth Taylor), Supporting Actress (Sandy Dennis), Black-and-White Art Direction, Black-and-White Cinematography, and Black-and-White Costume Design
Based on the legendary 1962 stage play by Edward Albee, Mike Nichols‘ Who’s Afraid of Virginia Woolf? is far and away one of the most impressive film directing debuts in Hollywood history. It’s also the vehicle for one of the most undeniable Best Actress Oscar wins of all time, as Elizabeth Taylor‘s performance here is an absolute tour-de-force.
But that towering performance isn’t the only thing this masterpiece has going for it, nor was it its only Oscar victory. However, while Virginia Woolf was the biggest nominee of the night with 13 nods (it’s one of the few films ever to be nominated in every single category it was eligible for), it wasn’t the biggest winner of the night. That title went to what the Academy deemed to be the Best Picture of 1966, the historical drama A Man for All Seasons, which won 6 Oscars in total. It’s a fantatsic film, indeed, but whether it’s superior to Nichols’ debut is up for debate.
9
‘Doctor Zhivago’ (1965)
Won: Adapted Screenplay, Color Art Direction, Color Cinematography, Color Costume Design, and Original Score
David Lean was the undisputed king of the epic film genre, a master of his craft who used his artistic skills to make some of the biggest, most sweeping motion pictures of his time. That includes Doctor Zhivago, a historical romance based on Boris Pasternak‘s 1957 novel. To date, it remains the 9th highest-grossing film of all time internationally after adjusting for inflation. No wonder.
It may not be Lean’s best, but it’s still a marvelous cinematic achievement, as well as one of the most perfect romantic war movies ever made. It very well could have won Best Picture, but it happened to be nominated in 1966 alongside a movie that had just as many nominations and wins as it did (ten and five, respectively): the beyond-iconic musical The Sound of Music, no doubt a deserving winner.
8
‘The King and I’ (1956)
Won: Actor (Yul Brynner), Color Art Direction, Color Costume Design, Sound Recording, and Musical Picture Scoring
Based on the iconic 1951 Rodgers and Hammerstein stage musical, Walter Lang‘s The King and I is one of the best Hollywood musicals of the ’50s. It was a critical and commercial success that was praised for its story, its tunes, and its impressive production values. It had quite a bit of buzz going into the 1957 Academy Awards, but it wasn’t really a frontrunner.
That race, precursors had set up a race between the James–Dean-starring Giant (the biggest nominee of the ceremony, with 10 total nods) and what would end up becoming another one of the most controversial Best Picture recipients ever, Around the World in 80 Days. That movie tied with The King and I as the biggest winner of the night, with five total wins. Though Giant would definitely have been the Best Picture winner that would have aged the best from this lineup, The King and I would undoubtedly have been more deserving than the actual winner.
7
‘A Place in the Sun’ (1951)
Won: Director (George Stevens), Screenplay, Black-and-White Cinematography, Black-and-White Costume Design, Film Editing, and Dramatic or Comedy Picture Scoring
George Stevens‘ tragedy film A Place in the Sun is one of those somewhat forgotten ’50s movies that have aged like fine wine and deserve a re-discovery. Based on Theodore Dreiser‘s 1925 novel An American Tragedy and the 1926 stage play of the same title, the film was also inspired by Chester Gillette‘s murder of Grace Brown in 1906.
At the 24th Academy Awards, the most nominated film was A Streetcar Named Desire, with 12 nods. The biggest winners, however, were A Place in the Sun and the ceremony’s Best Picture winner: Gene Kelly‘s endearing musical An American in Paris, both of which won 6. Fittingly, both were the precursor frontrunners that season, American in Paris having won the first-ever Best Comedy or Musical Golden Globe and Place in the Sun having won the first-ever Best Drama Golden Globe, on the first year that Best Picture was split into two at the Globes.
6
‘Dune’ (2021)
Won: Original Score, Sound, Film Editing, Cinematography, Production Design, and Visual Effects
Frank Herbert‘s Dune is one of the greatest sci-fi book masterpieces of all time. As such, and especially after David Lynch‘s panned 1984 adaptation and Alejandro Jodorowsky‘s failure to get his adaptation made at all, it was believed that it was impossible to make a film worthy of Herbert’s legacy. Enter Denis Villeneuve, easily one of the most talented filmmakers working in Hollywood today.
Villeneuve knocked it out of the park with 2021’s Dune, and proved that the material was in more-than-capable hands. What better demonstration than a whopping six Oscar wins, the most of any film from the 2022 Academy Awards? The ceremony’s biggest nominee was Jane Campion‘s The Power of the Dog, but the Best Picture recipient actually ended up being neither of these two films. That honor went to CODA, which won all three Oscars it was nominated for, making it one of less than 10 films that have ever gotten Best Picture without losing in any category. Dune was never really a frontrunner this season, but its being the biggest winner of the night speaks volumes.
5
‘La La Land’ (2016)
Won: Director (Damien Chazelle), Actress (Emma Stone), Cinematography, Original Score, Original Song (“City of Stars”), and Production Design
Alas, the 2017 Academy Awards will forever be infamous for the Best Picture announcement mix-up; but that should never detract from the praise that the year’s two best films, Barry Jenkins‘ Moonlight and Damien Chazelle‘s La La Land, most definitely deserve. As one of the movies with the most Oscar nominations in history, La La Land is simultaneously a wonderful homage to classic musicals and a marvelous, dazzlingly original musical in its own right.
It had both the most nominations and the most wins of the night, with 14 and six, respectively.
The movie is a technical wonder; so, rather unsurprisingly, it had both the most nominations and the most wins of the night, with 14 and six, respectively. It was neck-and-neck with Moonlight as the Best Picture frontrunner for pretty much the whole 2016-17 awards race; and, in the end, the best thing that could have happened did happen. Moonlight walked away with Best Picture, while La La Land walked away as one of the biggest Oscar winners in history.
4
‘Mad Max: Fury Road’ (2015)
Won: Costume Design, Film Editing, Makeup and Hairstyling, Production Design, Sound Editing, and Sound Mixing
After two Happy Feet movies and three decades away from Max Rockatansky’s wasteland, George Miller returned to the action genre in spectacular fashion. At first, Mad Max: Fury Road seemed like a legacy sequel like any other. As soon as it came out, however, fans of the genre immediately came to recognize it as one of the greatest action flicks of the 21st century. That reputation hasn’t died down.
It’s one of the blockbuster action movies with the best acting, even if none of its 10 nominations (the second most of the year, after The Revenant‘s 12) were for acting. It was far and away the biggest winner of the night, and deservedly so. Though this was one of the most unpredictable Best Picture races of the 2010s, Fury Road was rarely ever predicted to win. Instead, the Academy went for something far more subtle and socially sharp: Spotlight, one of the few Best Picture winners in history with only two Oscar wins in total. But endurance as a modern classic always ends up being the biggest award of all, and that’s something that Fury Road has in droves.
3
‘Star Wars: Episode IV — A New Hope’ (1977)
Won: Art Direction, Costume Design, Film Editing, Original Score, Sound, and Visual Effects
George Lucas‘ Star Wars needs no introduction. It’s nothing short of the biggest and most popular transmedia franchise in history, but it all had to begin somewhere—and in this case, that somewhere was 1977’s Star Wars, now retroactively called Episode IV — A New Hope. The movie had one of the longest theatrical runs of all time, and it isn’t hard to see why: It’s pure, enthralling, absolute movie magic.
Not counting its Special Achievement Award and its Scientific and Engineering Award, Star Wars won six Oscars, the most of any film from the 50th Academy Awards. It was also nominated for another four, though the most nominated movies of the year were Julia and The Turning Point. The Best Picture winner of 1978, however, was one of the greatest rom-coms ever made: Annie Hall, which also won another three Oscars. The court of public opinion matters most, though, and there’s no doubt about it: Star Wars is, and perhaps forever will be, the most iconic film of 1977.