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Part 1/10:

The Top 10 Oscar Wins That Didn't Age Well

As we reflect on the history of the Academy Awards, some wins seem to stand out for all the wrong reasons. This article takes a look at the top 10 Oscar victories that have not aged well, centering primarily on the key categories of Best Actress, Best Actor, Best Director, and Best Picture. The selections are not necessarily the worst wins in Oscar history, but rather those that provoke a sense of confusion or surprise when viewed in hindsight.

10. Best Actress: Helen Hunt - As Good As It Gets

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Part 2/10:

Helen Hunt’s win for Best Actress in As Good As It Gets feels increasingly perplexing 25 years later. While there is no dispute over the quality of performances in the film, it's hard to ignore Judy Dench’s outstanding portrayal in Mrs. Brown, which Hunt herself acknowledged in her acceptance speech. Some take a view that Hunt's Oscar was a popularity contest, stemming from her successful television career at the time.

9. Best Director: Kevin Costner - Dances with Wolves

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Part 3/10:

Kevin Costner’s Oscar for Best Director for Dances with Wolves is another questionable choice. The film was indeed his directorial debut, but many critics argue that Martin Scorsese’s masterful direction in Goodfellas deserved the award. The Academy often favors epic films for these honors, but leaving Scorsese empty-handed on two significant occasions seems a significant oversight.

8. Best Picture: Green Book

The awarding of Best Picture to Green Book at the 2019 Oscars continues to cause discomfort among film enthusiasts. Though the film was well-received and entertaining, it emerged over stronger contenders such as Roma and A Star Is Born. It exemplifies a trend where the film with broader appeal, rather than the most passionate support, takes home the Oscar.

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Part 4/10:

7. Best Actor: Art Carney - Harry and Tonto

Art Carney's victory for his role in Harry and Tonto over more iconic performances such as Jack Nicholson in Chinatown and Al Pacino in The Godfather Part II leaves many shaking their heads. The Academy awarded Carney when it arguably had more deserving candidates that year, as it is difficult to fathom such an upset given the caliber of the performances.

6. Best Actor: Al Pacino - Scent of a Woman

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Part 5/10:

Al Pacino finally won his Oscar for Scent of a Woman, but this accolade is often seen as underwhelming given the competition. Many believe Pacino's winning performance doesn’t hold a candle to his earlier work in The Godfather series, where he was notably overlooked. Furthermore, Denzel Washington’s compelling role in Malcolm X was arguably more deserving of recognition in this competitive year.

5. Best Director: John G. Avildsen - Rocky

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Part 6/10:

While Rocky is quite deserving of its Best Picture win, the directing accolade for John G. Avildsen receives mixed reviews. Critics argue that a more skilled director, such as Sidney Lumet for Network, should have been awarded for their exceptional filmmaking. Avildsen’s win feels like a missed opportunity to recognize true cinematic excellence.

4. Best Actor: Roberto Benigni - Life Is Beautiful

Roberto Benigni's win for Best Actor for Life Is Beautiful remains a controversial subject. While the film won Best Foreign Language Film, many believe his performance didn't surpass the talents of nominees like Tom Hanks and Ian McKellen. This win raises eyebrows, particularly as the Academy seems to have favored Benigni thanks to aggressive campaigning.

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Part 7/10:

3. Best Actress: Gwyneth Paltrow - Shakespeare in Love

Gwyneth Paltrow’s Oscar for Shakespeare in Love is scrutinized due to strong alternatives, notably Cate Blanchett in Elizabeth and Fernanda Montenegro in Central Station. Paltrow’s win feels more like a product of her popularity rather than the strength of her performance, as many feel it was another case of the Academy rewarding star power over acting prowess.

2. Best Picture: Shakespeare in Love

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Part 8/10:

Similarly, Shakespeare in Love winning Best Picture over Saving Private Ryan is widely considered a misstep. The historical drama by Steven Spielberg is revered and frequently revisited, whereas the whimsy of Shakespeare in Love has not withstood the test of time. The award is often linked to the controversial influence of Harvey Weinstein during the campaign.

1. Best Picture: Crash

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Part 9/10:

At the top of the list is the Best Picture win for Crash at the 78th Academy Awards, which is regarded as one of the most misguided choices in Oscar history. Many argue that Brokeback Mountain was a far superior film deserving of the recognition, having swept numerous awards leading up to the ceremony. The sentiment persists that Crash won not on its merit, but rather as a backlash against a competitor that the Academy was hesitant to fully embrace.

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Part 10/10:

In conclusion, these Oscar wins serve as reminders that time can reshape our perceptions of film and acting quality. As sentiments evolve, these victories—once celebrated—are often looked upon with a mixture of disappointment and bemusement. The Academy may want to reflect on these choices as they move forward in honoring cinematic excellence.

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