In this fourteenth part of my retrospective Oscar Outlook, I’ll be eliminating a pair of films that won Best Picture prizes at the same ceremony, an X-rated masterpiece, and one of the most influential films of the past 20 years.
20. “Wings” (1927/28)
Before “Top Gun: Maverick,” there was “Wings.” The Academy did itself a favor when it gave this picture its first mega-prize, giving the group credibility for decades. There are moments in “Wings” that I simply cannot wrap my mind around on a technical level. I’m not just thinking of the flying scenes, all of which are stunning. The on-the-ground scenes are very impressive, both in story and in the way the camera moves. And the narrative works as a simple but effective melodrama, thanks to excellent physical performances across the board. Great taste from the jump, Oscars.
19. “Midnight Cowboy” (1969)
One of the coolest choices ever made by the Academy was awarding “Midnight Cowboy,” an X-rated counterculture film, the Best Picture Oscar. There’s no way it would be rated so controversially these days, but “Midnight Cowboy” has retained its edge. It’s got some trippy Andy Warhol energy, mixed with some serious darkness. Yep, that’s pretty much the 1960s in a nutshell. This was a really good way for the decade to go out and, juxtaposed with the 1960 winner “The Apartment,” shows how much the industry had changed in a span of 10 years.
18. “Moonlight” (2016)
“Moonlight” pulled a mega-upset over “La La Land” (though it appeared briefly in doubt), and I don’t dislike the choice. The first pieces of “Moonlight” that stand out to me are the cinematography and the music. In tandem, they form an artsy, gritty energy that I can’t immediately connect to any other viewing experience. These technical elements serve a heartbreaking story of forbidden love. It won in the direct aftermath of Donald Trump’s first inauguration, and it couldn’t have been a subversive choice. The story of Chiron was relatable to so many because, unfortunately, we live in a society where normal desire is regularly suppressed.
17. “Sunrise” (1927/28*)
Technically the winner of the “Best Unique and Artistic Picture” award – rather than the one for “Outstanding Picture” – at the 1st Academy Awards, “Sunrise” adds prestige to the Best Picture canon. Those of us who are invested in such things always include it on a list like this one. Its revolutionary score and German Expressionist sensibilities are still highly valued in the modern industry. I find its tone to be delightfully unsettling, and more impactful than any other silent film I’ve seen.
16. “The Bridge on the River Kwai” (1957)
In discussing “From Here to Eternity,” I complimented that film’s interweaving narratives. “The Bridge on the River Kwai” does that even better. The Alec Guinness half of the film is borderline frustrating, with Guinness’ Col. Nicholson being committed to the point of fanaticism. On the other hand, William Holden’s Shears is nearly the more competent of our two protagonists, though his entire character structure is built on a lie. Their mostly indirect clash at the end is the kind of energy only the medium of film can bring.
Sam Zavada is counting down his ranking of every Best Picture winner in the history of the Academy Awards in the lead up to this year’s ceremony on March 2. Participate in the Times Leader Readers’ Ballot for the 97th Oscars by filling out the form at https://bit.ly/4hd8n6F. The Readers’ Ballot will close on Friday, Feb. 27, at 8 p.m. and will be revealed in the Saturday, March 1, edition of the Times Leader.
Sam Zavada is counting down his ranking of every Best Picture winner in the history of the Academy Awards in the lead up to this year’s ceremony on March 2.