A List of Oscar-Winning Films That Are Considered Problematic Today

Winning an Oscar is considered the highest achievement in cinema, but not all winners stand the test of time.

Some films, once celebrated, now carry an uncomfortable weight due to their outdated themes, problematic portrayals, or revelations about the filmmakers behind them.

What was once deemed revolutionary or even progressive at the time can now seem tone-deaf, racist, sexist, or just plain wrong.

With the 2025 Oscars around the corner, it’s worth revisiting some of the Academy’s past Best Picture winners that have aged… well, let’s just say not like fine wine.

Some of these films sparked controversy from the start, while others only faced backlash years later, as societal norms and cultural awareness evolved.

Here are 11 Oscar-winning films that, for one reason or another, don’t quite sit right today.

1. Gone With the Wind, 1940 

Few films have shaped Hollywood like Gone With the Wind, a cinematic giant that won 10 Academy Awards, including Best Picture. However, while the film was praised for its scale and storytelling, it also romanticized the antebellum South and perpetuated racial stereotypes.

Hattie McDaniel became the first Black actor to win an Oscar for her role as Mammy, but her treatment at the ceremony was anything but celebratory—she was forced to sit at a segregated table. Even in the 1930s, protests emerged against the film’s racist undertones, and its portrayal of slavery has only become more problematic with time. Calls to “re-examine” Gone With the Wind resurfaced in 2020, leading streaming platforms to add disclaimers about its content.

2. Annie Hall, 1978

Annie Hall is widely regarded as one of the best romantic comedies of all time, winning four Oscars, including Best Picture. But in light of sexual assault allegations against director Woody Allen—brought forward by his adopted daughter Dylan Farrow—the film carries a different weight today.

Allen's recurring theme of older men pursuing much younger women (often played by himself) was already unsettling, but the allegations make it even harder to watch. Hollywood stars like Timothée Chalamet and Selena Gomez have since distanced themselves from Allen, with some donating their salaries from his films to charity.

3. Driving Miss Daisy, 1990 

When Driving Miss Daisy won Best Picture, it was seen as a warm-hearted, progressive story about racial reconciliation. But over time, critics—and even lead actor Morgan Freeman—have pointed out its flaws.

The film follows the friendship between an elderly white woman and her Black chauffeur, played by Freeman. However, it has been criticized for oversimplifying racism, presenting a patronizing “white savior” narrative, and glossing over systemic discrimination. Spike Lee’s Do the Right Thing, which tackled racism more head-on, wasn’t even nominated that year, highlighting Hollywood’s preference for palatable over powerful.

4. The Silence of the Lambs, 1992

There’s no denying that The Silence of the Lambs is an iconic thriller, but its portrayal of Buffalo Bill has long been a point of contention.

The serial killer’s obsession with wearing women’s skin led to protests from LGBTQ+ activists, who argued that the film reinforced harmful transphobic stereotypes. Director Jonathan Demme later apologized, stating that Bill was never intended to be portrayed as transgender. However, intent doesn’t always match perception, and for many, the damage was already done.

5. Forrest Gump, 1995

Tom Hanks' lovable Forrest charmed audiences, but Forrest Gump has faced criticism for oversimplifying history and reinforcing conservative ideals.

The film portrays Jenny—Forrest’s love interest—as a tragic figure whose journey through counterculture, feminism, and activism leads to self-destruction, whereas Forrest’s apolitical, obedient nature is rewarded. The story also largely ignores the real struggles of Vietnam War veterans and people with disabilities.

6. Braveheart, 1996

Mel Gibson’s Braveheart was a crowd-pleaser, but historians were quick to call out its wildly inaccurate portrayal of Scottish history. That’s not the only reason it’s aged poorly—Gibson himself has been repeatedly accused of racism, anti-Semitism, and misogyny.

His troubling remarks and behavior over the years cast a shadow over his Oscar-winning work, making it difficult to separate the art from the artist.

7. American Beauty, 1999

American Beauty was hailed as a masterpiece when it won Best Picture, but its central storyline—about a middle-aged man lusting after his teenage daughter’s best friend—feels deeply uncomfortable today.

Kevin Spacey’s real-life sexual misconduct allegations only add another layer of unease to the film, making it one of the most troubling Oscar winners in hindsight.

8. The Pianist, 2003

Roman Polanski’s Holocaust drama The Pianist is a powerful film, but its Oscar win is controversial because Polanski himself is a fugitive from the U.S. justice system.

Having pled guilty to the sexual assault of a 13-year-old girl in 1977, Polanski fled the country and has lived in exile ever since. Yet, Hollywood continues to celebrate his work—though he was finally expelled from the Academy in 2018.

9. Crash, 2005

Crash winning Best Picture over Brokeback Mountain remains one of the most debated moments in Oscar history. The film, which aimed to tackle racism, has been widely criticized for its oversimplified, heavy-handed approach to race relations.

Even its director, Paul Haggis, has admitted it didn’t deserve to win.

10. Dallas Buyers Club, 2013

Jared Leto won an Oscar for playing a trans woman in Dallas Buyers Club, but critics argue that an actual trans actress should have been cast in the role.

Beyond casting issues, the film also falls into harmful tropes, portraying Leto’s character primarily as a plot device to make the straight, cisgender protagonist (played by Matthew McConaughey) look better.

11. Green Book, 2019

Green Book took home Best Picture, but many saw it as yet another film that presented racism through the lens of a white protagonist. Don Shirley’s family condemned the film’s depiction of him, and director Spike Lee famously tried to walk out of the ceremony in protest.

The Oscars have long been Hollywood’s biggest night, but looking back, it’s clear that some past winners haven’t aged well.