10 Oscar-Winning Movies That Haven't Aged Well

They made some right turns to win those golden statuettes. But in the harsh light of 2023, they start to look more like golden raspberries.

1. "Driving Miss Daisy" (1989)

The cinematic equivalent of a well-intentioned grandma who thinks it's still appropriate to pinch people's cheeks at parties, "Driving Miss Daisy" can be a little...cringe-inducing in modern times. Sure, the film took home the Best Picture Oscar, and Jessica Tandy's performance as an aging Southern Belle was charming enough to snag her the Best Actress award. However, the movie's portrayal of race relations has aged like cheese in the sun – it stinks.

In the film, Morgan Freeman plays Hoke, a kind, patient, black chauffeur serving the oftentimes condescending Miss Daisy. It's a well-meaning story about friendship crossing racial lines, but it often falls into the trap of the "Magical Negro" trope, where black characters exist mainly to help white characters evolve. Today's audiences demand more complex and authentic representation.

2. "Crash" (2004)

No, not the one about people who get off on car accidents. This "Crash" was a star-studded drama that attempted to tackle racial tensions in post-9/11 Los Angeles. It shocked everyone by snatching the Best Picture Oscar from "Brokeback Mountain." While it might have been timely in 2004, the film now feels heavy-handed and simplistic in its approach to racial dynamics.

Characters are one-dimensional, their prejudices clearly defined, and their personal growth over-dramatized. "Crash" wants so badly to say something profound about racism, but ends up saying very little, falling into the trap of creating caricatures rather than nuanced characters. It's the cinematic equivalent of a well-meaning but clueless friend who assures you they're "woke" because they retweeted a social justice post.

3. "American Beauty" (1999)

"American Beauty" was a movie that seemed to resonate with a generation of middle-aged men going through midlife crises. Its exploration of suburban disillusionment was all the rage at the turn of the millennium. It bagged a boatload of Oscars, including Best Picture, Best Director, and Best Actor for Kevin Spacey.

Fast forward to now, and the film's flaws are as glaring as the neon sign at a tacky motel. Lester Burnham's (Kevin Spacey) infatuation with his teenage daughter's friend, played by Mena Suvari, comes off as creepy rather than transformative. It's harder to see it as a critique of suburban emptiness when it leans into the 'older man/younger woman' trope so enthusiastically. Add to that the allegations against Spacey, and "American Beauty" has wilted more than its symbolic roses.

4. "The Birth of a Nation" (1915)

You know that uneasy feeling when you find out your favorite childhood story has some seriously problematic undertones (I'm looking at you, "Peter Pan")? That's pretty much how modern viewers feel about "The Birth of a Nation." Despite being groundbreaking in its filmmaking techniques, it is notoriously known for glorifying the Ku Klux Klan and promoting white supremacy. Sure, it was a different era, and it didn't win an Oscar as they didn't exist until 1929, but it was retrospectively acknowledged as one of the best films of the silent era. But any film that presents the KKK as heroic vigilantes isn't going to age well. In fact, it's aged about as gracefully as a banana in a heatwave.

5. "Gone with the Wind" (1939)

"Gone with the Wind" is like that old relative at family gatherings who keeps saying, "Back in my day." Yes, it was a cinematic marvel in 1939, sweeping up eight Academy Awards, including Best Picture. The performances were top-notch, the love story was epic, and the production values were jaw-dropping. However, it glossed over the atrocities of slavery and painted a rather rosy picture of the old South. Today, the film's romanticized portrayal of the Confederacy and the antebellum South seems tone-deaf at best and offensive at worst. Like Scarlett O'Hara holding onto her love for Ashley, the film clings to a past that's best left behind.

6. "Dances with Wolves" (1990)

"Dances with Wolves" was the cinematic equivalent of eating kale before it was cool – it was a big deal back then, but it hasn't aged well. Kevin Costner's film tells the story of a Union Army lieutenant who befriends a tribe of Lakota Indians. While it was a hit in 1990, bagging seven Oscars including Best Picture, the film's portrayal of Native Americans through a white perspective now feels outdated. Moreover, the trope of the "white savior" comes off as condescending in today's context. Let's face it, if the film were a cheese, it would be a moldy, smelly blue.

7. "Forrest Gump" (1994)

I know, I know, "Forrest Gump" is an absolute darling, and it won a whopping six Oscars, including Best Picture. But here's the thing, it's like a charming friend who never seems to grow up. Sure, Tom Hanks' performance as the slow-witted but kind-hearted Forrest is endearing, but the film's oversimplified narrative feels rather insubstantial. The movie's take on historical events through the lens of an intellectually disabled man borders on the simplistic, and its treatment of Jenny's character – the troubled love interest – is questionable at best. It's like someone enthusiastically telling you a story, but leaving out all the crucial details.

8. "The Artist" (2011)

You know that one friend who gets a vintage record player and suddenly won't shut up about the authenticity of vinyl sound? "The Artist" is the film equivalent of that friend. This silent black-and-white film, a homage to the bygone era of Hollywood, won a surprising five Academy Awards, including Best Picture. However, in retrospect, its silent shtick feels more like a gimmick than an essential narrative choice. "The Artist" is like a beautifully wrapped gift that, upon opening, turns out to be socks. It's nice, it's functional, but you can't help but feel a little disappointed. The film's charm has worn thin, and it now feels less like a timeless classic and more like a fleeting novelty.

9. "A Beautiful Mind" (2001)

Remember when everyone loved those biopics about brilliant individuals overcoming adversity? Well, "A Beautiful Mind" was the king of that particular hill, winning four Oscars, including Best Picture. The film tells the story of John Nash, a mathematical genius struggling with schizophrenia. While Russell Crowe's performance is commendable, the film's treatment of mental illness is problematic, romanticizing and oversimplifying the complexity of schizophrenia. Additionally, the film has been criticized for whitewashing some aspects of Nash's life. Like a well-meaning but misinformed friend, "A Beautiful Mind" means well but falls short in its execution.

10. "Green Book" (2018)

And finally, we arrive at "Green Book," a film that was controversial even before it snagged the Best Picture Oscar merely 5 years ago. The movie tells the story of an unlikely friendship between a black classical pianist, Don Shirley (Mahershala Ali), and his Italian-American chauffeur, Tony Vallelonga (Viggo Mortensen). The issue? Its clichéd and simplistic portrayal of racism, which comes off as a white-savior narrative, all seen primarily through Tony's perspective. It's like someone tried to explain racism through a series of post-it notes. In today's world, where audiences are more socially and politically conscious, "Green Book" has aged as well as milk left in the sun.