Which movie features the most Oscar-winning actors?
Most actors would be loath to admit that they take on particular roles with award potential in mind, but there is no denying that festival season is clogged with Oscar-baiting performances. Sometimes, it works out spectacularly well, such as when Charlize Theron attempted to conceal her blinding movie star looks for Monster or when Matthew McConaughey stepped out from behind his rom-com shadow to make Dallas Buyers Club. Other times, it’s just awkward, like when Jared Leto went full cartoon character in The House of Gucci or Naomi Watts put on a tiara to play Princess Di.
The question is, should actors seek out projects where they will be able to shine on their own or where they will be able to go toe-to-toe with some of the greats? In other words, if your goal is purely to win an Oscar, is it best to turn down the chance to work with Meryl Streep, or should you be going out of your way to snag her as your co-star?
You might think that the answer is impossible to pin down, but there is a very specific way to get close to it. If you run down the list of movies that star the most previous and future Oscar winners, you will find that none of them earned nominations, let alone won, Oscars for acting. At the top of the heap is Robert Altman’s The Player, a 1992 satire of Hollywood that featured no fewer than 12 Oscar winners. Everyone from Jack Lemmon to Julia Roberts appeared in the film, though it probably shouldn’t count, considering that most of them were playing themselves.
Next on the list is a three-way tie between 1956’s Around the World in 80 Days, 1965’s The Greatest Story Ever Told, and 1996’s Hamlet, each of which starred eight Oscar winners. The sheer number of excellent performances must have paralysed the Oscar voters because not one of those actors was nominated for their work, even as the films themselves earned multiple nods from the Academy. Around the World in 80 Days even walked away with ‘Best Picture.’
So, if you’re an actor angling for an Oscar, you might want to counterintuitively steer clear of a cast of heavy hitters.
Which film won the most acting Oscars?
What does it mean to sweep the Oscars? For some, it means that the movie won a record number of awards. But that metric tends to favour movies that can be nominated in a wide range of technical categories, like special effects and makeup, which rules out more contained, realistic stories like Nomadland and Moonlight. A more widely accepted metric is which movies have won ‘the Big Five’ – ‘Best Picture’, ‘Best Director’, ‘Best Actress’, ‘Best Actor’, and ‘Best Screenplay’.
Only three films have met this benchmark: It Happened One Night, One Flew Over the Cuckoo’s Nest, and The Silence of the Lambs. But there is another metric that is even more competitive. To date, no film has won an Oscar for all four acting categories, even though dozens have earned nominations in all four categories. Clearly, stacking the deck by cramming a movie with Oscar heavyweights isn’t the way forward, but having four distinct, meaty roles has so far yielded the closest to a perfect sweep.
Only three have won three acting Oscars: A Streetcar Named Desire, Network, and Everything Everywhere All at Once, two of which (and I won’t name names) had three excellently-written central characters. Ultimately, though the Oscars are not a perfect science, no matter how much that pomp and circumstance tries to convince us otherwise, and the awards often come down to which movies had the strongest campaign and which actors had the most momentum and goodwill going into the awards season.
