Oscar-Winning Movies That Didn’t Age Well In Hindsight
Taste is a subjective thing, so it stands to reason that not everyone is going to agree on how the awards are doled out at the Oscars. Still, even with this in mind, the Best Picture winner at the Academy Awards is supposed to represent the pinnacle of filmmaking — and history has shown us that this isn’t always the case.
From movies that scored wins over more deserving films to those that just haven’t stood the test of time, these are the Oscar winners that have aged poorly.
Crash (2004)

The modern-day poster child for Oscar winners that have aged like milk, 2004’s Crash attempted to take a thoughtful look at race relations in modern America — a task that, most agree, the film failed miserably at.
Crash essentially lets anyone with a guilty conscience off the hook by portraying racism as an aimless, chaotic force of nature rather than something with a long and nuanced history. One would hope that a film about racism would at least explore the systemic causes of racism, but Crash fails to do so.
Green Book (2018)

Green Book isn’t an especially bad movie, but it’s still somewhat surprising that its warmed-over depiction of racial relations was enough to earn a Best Picture nod.
Mahershala Ali and Viggo Mortensen do a fine job playing an African-American pianist and his driver/bodyguard as they tour the American South in 1962, but what should be a deep story is instead aggressively light and smooth. Critics contended that it was largely relying on the tired “White savior” trope.
Dances with Wolves (1990)

Kevin Costner’s directorial debut, Dances with Wolves, won big at the Oscars, but this sweeping historical effort seemed to be convinced of its own grandeur — and throughout its three-hour runtime, it generally fails to live up to this high bar.
Part of the reason for Dances with Wolves aging so poorly is the fact that it hasn’t really gone down as a classic, while nearly all of its competitors from that year’s Oscars — including Goodfellas and Ghost — are more fondly remembered today.
Cimarron (1931)

On one hand, it’s unfair to apply modern sensibilities to decades-old stories. On the other hand, Cimarron is a uniquely offensive film, even if it was well-received on its release.
Cimarron gleefully portrays virtually every race and creed, from Jewish to Indigenous people, as inferior to White Protestants. It dabbles in sexism as well by showing women as wilting flowers who need to be saved by strong men. While many older movies have racially questionable undertones, Cimarron shows its bias right on the surface.
Gone with the Wind (1939)

Many of those who would call Gone with the Wind a classic likely haven’t watched the film all the way through. Any movie set against the backdrop of the Civil War is going to have some difficult issues to deal with, and Gone with the Wind tackles this issue by simply glossing over them.
The film embraces the popular “lost cause” narrative and takes a decidedly pro-Confederacy stance. While it’s mostly centered around White characters, it veers sharply into stereotypes whenever it deals with anyone who isn’t White.
Cavalcade (1933)

1933’s Cavalcade might be seen as an early precursor to modern-day Oscar bait. After all, the film displays impressive attention to detail and tells a grand, sprawling story that juxtaposes one family’s life against major historical events.
However, the story told in Cavalcade isn’t particularly cohesive, and its western-focused perspective doesn’t dig very deep. When it won Best Picture at the Oscars, it set a trend for the Academy favoring big budget, safe films.
The King’s Speech (2010)

A movie about the king of England dealing with a speech impediment sounds like a deeply boring story to tell, and indeed, The King’s Speech is a rather uninteresting movie. While Colin First is capable in the lead role and the set design is accurate to the era, The King’s Speech feels like a story that didn’t really need to be told.
All in all, The King’s Speech feels like classic Oscar bait: A movie that was made and released with the sole intent of winning as many gold statuettes as possible.
American Beauty (1999)

Even before Kevin Spacey became persona non grata in Hollywood, there were misgivings around handing American Beauty Best Picture at the Oscars. Not only is Spacey’s character in the movie grating in many ways — he has many deep complaints for someone whose life doesn’t seem that bad — but his character’s desires are questionable at best.
A central theme of the film is Spacey’s character fantasizing about his daughter’s teenage best friend. While the film doesn’t exactly endorse the fantasies, it also continues to portray Spacey’s character in a positive light.
Gigi (1958)

Considering how concerned society is with grooming and age-inappropriate relationships, it’s somewhat worrying how often these themes are included, and even celebrated, in mainstream entertainment.
A perfect example is Gigi, which won Best Picture at the Oscars for its story of a 16-year-old girl who’s groomed to be a courtesan. As if the theme wasn’t clear enough, it featured a song called “Thank Heaven for Little Girls.” This was enough to win it not just Big Picture, but eight other Oscars as well.
The Broadway Melody (1929)

The Broadway Melody certainly deserves its place in film history as the first film with sound to win Best Picture (not to mention a Technicolor sequence), but technical achievements aside, this is no one’s idea of a timeless film.
Shot as a musical, The Broadway Melody is a deeply boring and conventional story. It might not be fair to apply modern sensibilities to a film that’s nearly a century old, but The Broadway Melody is a film caught between two worlds — that of silent film and that of the talkies — and does neither particularly well.
One Flew Over the Cuckoo’s Nest (1975)

It seems somewhat unfair to include this movie here. After all, it has stood the test of time and still tells a powerful and compelling story. However, one aspect that hasn’t aged well is part of the back story of its protagonist, Randle McMurphy, who was played by Jack Nicholson.
McMurphy is in the hospital in the first place because he assaulted a 15-year-old girl — a disturbing detail for a character who’s supposed to be sympathetic. While modern films might attempt to make a protagonist atone for a bad lapse in judgment, in this case, it’s barely acknowledged.
The Silence of the Lambs (1991)

Recent movies have taken a more nuanced look at the transgender experience, but it’s safe to say that The Silence of the Lambs came from a different time. Its portrayal of serial killer Buffalo Bill “making a women’s suit” would likely be seen as problematic if it came out a couple of decades later.
The movie makes it clear that Bill isn’t transgender, and also that there’s no link between transgender identity and violence. Still, this nuance is hard to parse in a movie that portrays a man in women’s clothes as a revolting sight.
The Greatest Show on Earth (1952)

The Greatest Show on Earth promises a grand time in its title, and to its credit, it certainly tries — but this drawn-out movie was way too long and way too bland to hold the attention of audiences.
With an eye-watering runtime of 152 minutes, the film tells a largely boring story of romance, set against the background of the circus world. In an era when films were generally shorter, this film stood out for its length — and served as a precursor to modern-day Oscar-bait films, which are often well over two hours long.
Shakespeare in Love (1998)

Shakespeare in Love had many elements to win over late ’90s audiences: A light and satisfying romance, historical opulence, and heartthrobs of the era heading up the cast. Still, it seems like a film that’s far too safe, tame, and overall forgettable to win Best Picture at the Oscars.
But win it did — beating out Saving Private Ryan — a decision that was questionable even at the time, and appalling in retrospect. In the years since, it’s become evident that disgraced producer Harvey Weinstein lobbied the Academy heavily to get the award.
Driving Miss Daisy (1989)

Driving Miss Daisy further cemented the perception that the Academy only wants to view movies with racial overtones if the plot stays light and lets the audience off the hook at the end.
Morgan Freeman plays his role as a chauffeur ably, but in the end, the film is just another story of a Black person who endures insults to serve the privileged. In 2015, The Hollywood Reporter stated that in a poll of Academy members, most would have awarded the Best Picture Oscar to My Left Foot instead.