5 Oscar Winners That Didn’t Age Like Fine Wine

Sure, snagging an Academy Award is every filmmaker’s dream, but as our social media feeds remind us daily, times change—and fast. Let’s take a nostalgia trip with a twist, revisiting five Oscar darlings that haven’t exactly aged like the fine wines we hoped they’d be.

1. Gone with the Wind (1939)

Let’s kick things off with “Gone with the Wind.” This epic saga swept through the Oscars like a hurricane, collecting eight statues along the way. It’s the OG blockbuster, complete with a whirlwind romance set against the American Civil War. But here’s the tea: its glossy portrayal of the Antebellum South and cringey racial stereotypes have aged as well as milk. While its place in cinema history is cemented, its legacy is now a mixed bag of admiration and side-eye glances.

2. Crash (2004)

Next up, “Crash” — the movie that blindsided Oscar night by beating out “Brokeback Mountain” for Best Picture. Meant to be a bold take on LA’s racial tensions, it now feels like a missed call. Critics and audiences alike have dubbed it the Academy’s awkward phase, proving that even Oscars can have moments they’d rather forget. The movie’s heart was in the right place, but its execution? Kinda like getting a “participation” trophy in adulting.

3. Around the World in 80 Days (1956)

Remember when “Around the World in 80 Days” was the ultimate cinematic adventure? Me neither. Winning Best Picture was no small feat, but let’s be real: the movie’s charm has deflated faster than a leaky air balloon. In today’s global village, the film’s “wow” factor is more of a “meh,” proving that a trip around the world is better off on your Insta feed than on a three-hour cinematic expedition.

4. Driving Miss Daisy (1989)

Cruising into the list is “Driving Miss Daisy”, a film that tried to navigate the rough roads of racial harmony. While it scored big on Oscar night, its portrayal of race relations now feels as fresh as last week’s leftovers. Like “Crash”, it’s a reminder that sometimes Hollywood’s road to understanding is more of a scenic route.

5. Breakfast at Tiffany’s (1961)

And who could forget “Breakfast at Tiffany’s”? Audrey Hepburn was the epitome of chic, but there’s one aspect of the film that’s impossible to gloss over: Mickey Rooney’s portrayal of Mr. Yunioshi. In today’s climate, it’s a cringe-fest of racial insensitivity that makes us want to hit “skip.” The film remains a fashion icon’s playbook, but this part? It’s like finding out your vintage Chanel is actually a knock-off.

These flicks are a mixed bag of cinematic milestones and face-palm moments. They remind us that art, like us, evolves. So, while we can appreciate these films for their achievements (and their place in our Netflix queue), it’s okay to acknowledge that some aspects haven’t quite stood the test of time. Let’s just say, they’re the kind of texts you read but don’t always endorse on your timeline.