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30 Movies That Should Have Won an Oscar

What’s Eating Gilbert Grape

What’s Eating Gilbert Grape was a movie of the decade. It had an all-star cast including John C. Reilly, Juliette Lewis, Johnny Depp, and a young Leonardo DiCaprio. In fact, this film was Leo’s breakout role. He played a developmentally disabled teen in a small town in such a way that critics praised him for his method acting. Best Picture went to Schindler’s List, so we can’t really disagree with that option. However, I think we can say Gilbert Grape should have won something.

It didn’t even get many nominations, with only one for Best Supporting Actor. That was the year Leonardo started his Oscar nomination streak. He lost to Tommy Lee Jones in The Fugitive, but I think it’s evident that Leo should have won that year. This movie showed us that DiCaprio would be the greatest actor of our age. At least we can say that he’s finally earned one for his work on The Revenant.

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Sunset Boulevard

Sunset Boulevard is one of the best movies of all time. The plot is flawless, the directing is skilled, and don’t even get me started on the acting. Gloria Swanson’s role as Norma Desmond is the stuff of legends. Somehow, All About Eve swept the awards in 1950, winning the most awards since Gone with the Wind. I respectfully disagree. Sunset Boulevard was the best picture of the decade.

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Rebel Without a Cause

The 50s helped define teenagers in film, and James Dean took it a step further by embodying the “bad boy” image. Rebel Without a Cause is cheesy but does a great job showing a coming of age story for a teen that’s just trying to find his place in life. Sadly enough, this was one of James Dean’s last films, and it’s hard to believe he didn’t win Best Actor. Not only did he lose to Ernest Borgnine in Marty, but he also didn’t get a nomination.

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Psycho

Psycho is horrifying and probably made you afraid to take a shower – it certainly made Janet Leigh afraid. After filming this movie, she opted for baths for years! Alfred Hitchcock was an ingenious director that wanted nothing short of perfection, and for that reason, he should have won Best Director for Psycho. Unfortunately, West Side Story swept the Oscars including Best Picture, Best Director, and Best Supporting Actor and Actress that year.

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Dead Poets Society

Dead Poets Society did win best original screenplay, but I’m going to argue that it should have won Best Picture. This film single-handedly inspired a generation with its “O Captain! My Captain!” scene. It also showed that literature and poetry could be enjoyable. Finally, it’s one of Robin Williams’s best roles.

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Fight Club

I know I’m breaking rule number one by putting Fight Club on the list, but I have to. Edward Norton and Brad Pitt were terrific, and the script was even better. It was impossible to see the twist coming, and we’re still quoting the lines nearly two decades later. Whether it gets an Oscar for Best Screenplay, Best Director, or Best Adaption – it doesn’t matter. The film didn’t get a single nomination. I am Jack’s inflamed sense of rejection.

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Star Wars: The Force Awakens

Star Wars: The Force Awakens was a movie that brought old and new fans of the series together. The film made over two billion at the box office and was overwhelmingly praised by critics and fans. The movie that won the Oscar that year? Spotlight. While it was a great movie, it just wasn’t “Best Picture” material. Even now, most people have forgotten this movie exists.

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Leon: The Professional

Leon: The Professional was a masterpiece. It featured Jean Reno, Gary Oldman, and an 11-year-old Natalie Portman. It’s impossible to say that Natalie Portman didn’t steal the show. From that point on, it was clear that she was going to become an acting powerhouse. That year, Forrest Gump won the Oscar for Best Picture. I’m not saying Leon: The Professional deserves Best Picture, but it certainly deserved the Oscar for Best Supporting Actress.

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The Shining

The Shining was absolutely terrifying during its heyday. Even Shelley Duvall, the actress who played Wendy, said it was the most challenging role she’d ever played because it was so traumatizing. The movie lost Best Picture to Ordinary People. Ordinary People was a good film, but The Shining proved to be more enduring.

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Memento

Memento is one of Christopher Nolan’s masterpieces, and he blew audiences away with the release of the film. Even now, the movie is fantastic to watch. Somehow, he manages not to lose the audience through the trippy story. Everything was plotted precisely, the script was breathtaking, and it didn’t win a single Oscar. Memento deserved an Oscar for Best Original Screenplay.

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Brokeback Mountain

Brokeback Mountain deserved Best Picture. This is one of the most controversial choices at the Academy Awards, and it’s still a complete injustice. Brokeback Mountain deconstructed the image of rugged cowboys. It also tackled a complicated topic and made a beautiful film, which was overwhelmingly superior to Crash (the winner) in every single way. Even Jack Nicholson was shocked as he read off the winner.

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The Wolf of Wall Street

The Wolf of Wall Street was easily one of the best films of 2013. The cast was astounding and included Leonardo DiCaprio, Margot Robbie, Jonah Hill, and Matthew McConaughey. The Oscars had tough competition that year with Dallas Buyers Club, 12 Years a Slave, and American Hustle, but Leo definitely should have won Best Actor. The Quaalude scene was one of his most astounding in all of film.

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Saving Private Ryan

How exactly is Shakespeare in Love better than Saving Private Ryan? It’s one of the best war movies ever, and when you look back at Shakespeare in Love, it looks like nothing more than a generic late 90s romance flick. The script was immersive, the actors stole your heart, and it was easy to find yourself praying the group makes it out alive.

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2001: A Space Odyssey

Stanley Kubrick has never really got his due for being one of the best directors ever to make movies. It’s unbelievable to think that 2001: A Space Odyssey didn’t even get a Best Picture nomination and didn’t win Best Director. Instead Oliver! took both awards. These days, 2001: A Space Odyssey is still one of the best sci-fi films of all time. Oliver who?

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The Sixth Sense

The Sixth Sense was one of M. Night Shyamalan’s best films. With that being said, The Sixth Sense deserved some sort of Oscar. It had audiences crying at the end, and everyone remembers the “I see dead people” scene. American Beauty swept the Academy Awards in 2000, which just wasn’t fair. 

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Boyhood

Boyhood was an ingenious film. It is a coming of age film that was shot over the course of 12 years using the same cast for an authentic look. It has a 97% Certified Fresh rating on Rotten Tomatoes, and audiences loved it. Somehow, this coming-of-age movie lost to Birdman for Best Picture and Best Director. It’s one of the worst offenses of the Academy Awards.

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The Shawshank Redemption

It’s honestly hard to believe that The Shawshank Redemption didn’t win a single Oscar. Audiences adored the movie, but Forrest Gump was somehow better in the eyes of the Academy. If it didn’t deserve a win Best Picture or Director, Morgan Freeman should have at least won Best Actor for his role as Red.

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Cat on a Hot Tin Roof

Cat on a Hot Tin Roof was nominated for six Academy Award but didn’t win a single one. This Tennessee William’s classic lost Best Picture to Gigi, an overblown musical. Cat on a Hot Tin Roof had a great cast with Elizabeth Taylor and Paul Newman, and even hired one of the best directors and screen writers of all time, Richard Brooks. Now, Cat on a Hot Tin Roof is seen as one of the best films of the 50s. It should have won Best Picture without a doubt.

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A Streetcar Named Desire

Marlon Brando’s portrayal in A Streetcar Named Desire has had audiences confused for a little while. Yeah, he was abusive, but he was also incredibly attractive. Putting that aside, the acting was fantastic. The emotions felt real and intense, making it hard to watch at times. The Best Picture Oscar went to An American in Paris, which is a great musical but doesn’t hold a candle to A Streetcar Named Desire.

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Pulp Fiction

Pulp Fiction had a lot of Oscar competition,  including The Shawshank Redemption, Forrest Gump, and Ed Wood. It did win Best Screenplay Written Directly for the Screen, but it should have gotten more. I’m not here to say it deserved a Best Picture Oscar, but Best Cinematography isn’t a stretch. The film wouldn’t be the glorious movie it is without its hued, pin-sharp widescreen images. It also combined Pop Art with Tarantino’s gritty, dark comedy.

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It’s a Wonderful Life

Many families still watch It’s a Wonderful Life every holiday season. Jimmy Stewart’s acting was marvelous and is still holds a great message that is still relevant today. The film was nominated five times for the Oscars but didn’t land a single award. At minimum, Stewart should have walked off with Best Actor.

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Se7en

Se7en was high acclaimed, but the Oscars somehow overlooked it. Some say that it was too dark and graphic for its time, but that doesn’t mean it deserved to be snubbed. The cast included Morgan Freeman, Brad Pitt, and Kevin Spacey, who all played their roles perfectly. Instead, Mel Gibson won Best Director for Braveheart, which also won Best Picture. Se7en didn’t even get a nomination.

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Shutter Island

Shutter Island came out the same year as Inception, so choosing between the two is tough, but it was undoubtedly overlooked as a great film. It didn’t receive a single nomination, which is a crime since its plot twist blew away audiences. It didn’t deserve Best Picture or Director, but it definitely did deserve Best Original Screenplay for the surprise ending.

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Goodfellas

Goodfellas is easily one of the best mob movies of all times – only topped by The Godfather. It’s also one of Scorsese’s best films, so why didn’t it win anything? Dances with Wolves was released that same year, but it now looks a little stale. Goodfellas really gave us great lines and even better acting—it deserved Best Picture that year. 

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Elizabeth

Elizabeth was far from the best movie of the year, but it certainly had the best costume design. This period piece showcased outfits that Queen Elizabeth herself would love to wear. Shakespeare in Love walked away with best costume design, which was disappointing. Judi Dench’s dress was fabulous, but almost every dress in Elizabeth was that stellar.

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Girlhood

Girlhood is a French, coming-of-age film about a girl who joins a gang and reinvents herself in the process when she realizes she isn’t happy. The film won 11 awards in total at several ceremonies including the Stockholm Film Festival and International Cinephile Society Awards. Girlhood deserved the Oscar of Best Foreign Film that year, or at least a nomination.

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Reservoir Dogs

How exactly is Unforgiven better than Reservoir Dogs? Now, Unforgiven stands as a typical western that enthusiasts seek out, but Reservoir Dogs is widely loved by critics and audiences alike. Tarantino is unapologetic in this brutal crime-thriller that leaves you on the edge of your seat. It didn’t even get a single nomination during the Oscars, which is a shame because it was the best picture of the year.

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Rear Window

Rear Window has a 100% Certified Fresh Rotten Tomatoes score and a 95% audience score. While it’s marginal a marginal difference, it’s still a better film than On the Waterfront, which won Best Picture in 1955. If not Best Picture, Rear Window deserved Best Director. In fact, Alfred Hitchcock never won an Oscar for Best Director during his entire career. The premise of Rear Window is unique, and the directing and editing shows us depths that no other director had accomplished at the time. 

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Les Misérables

Les Misérables should have won Best Picture. The most prominent mistake Les Misérables made was making the entire thing a musical – including the dialogue between songs. Despite this, Hugh Jackman gave one of the best performances of his career. Instead, Argo was chosen as Best Picture. Hugh Jackman could act circles around Ben Affleck – just look at the response when he was chosen as Batman.

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The Fellowship of the Ring

The Lord of the Rings trilogy is one of the best fantasy series ever made, but it was snubbed from the Oscars until Return of the King. While Return of the King was a great ending to the series, The Fellowship of the Ring should have won Best Director. A Beautiful Mind did deserve Best Picture for its portrayal of John Nash, but the directing couldn’t be compared to Peter Jackson’s Lord of the Rings epic.

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