The 20 Best Oscar-Winning Films of All Time
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Roll out the red carpet and brush up on your best pretentious hot takes, folks. In advance of this Sunday's Academy Awards, it’s time that we talk about the Oscars. All of them. (Well, except for the films up for awards at this year's ceremony—including the likely Best Picture winner, Oppenheimer.)
We're here to look back in cinema history and run down the best Oscar-winning films of all time. So, maybe you’ve been crafting your personal all-time ranking your whole life, chasing down every year’s Best Picture nominees in theaters and meticulously crafting a categorical bracket for your betting ring with your fellow cinephiles.
Or, maybe you’re just a film buff who knows everything from Wings to Parasite.Whether you’re here to expand your cinematic palette entirely, or just here for an bouche of gems you might have missed, we’ve gathered some crème de la crème picks for all kinds of moviegoers.
The Godfather Part II
The Godfather Part II is one of few films that managed to break the dreaded sequel curse, with a riveting film that explores Vito Corleone’s relationship with his son, Michael. The film cuts between two time periods, showcasing Vito’s arrival to Hell’s Kitchen in 1917 and his son’s introduction to crime in 1958.
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Rocky
Rocky's theme song alone makes this iconic sports film an Academy Awards heavyweight champion. The boxing epic stars Sylvester Stallone as Rocky Balboa, an amateur boxer who’s selected to fight the heavyweight champion Apollo Creed. While training for the big match, Rocky has to overcome the mental and physical challenges that hold him back. In 1977, Rocky took home five Academy Awards, including Best Picture.
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The Sound of Music
They don’t call it the greatest musical of all time for nothing! The Sound of Music is inspired by the Von Trapp family’s life story. Julie Andrews stars as Maria, a young Australian woman whom a widowed naval captain hires to care for his seven children. The film takes place ahead of World War II, when the Von Traps fled to America to avoid the Nazi regime. Despite the upheaval, Maria manages to restore their happiness and bring music into their household.
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The Departed
As Billy Costigan in The Departed, Leonardo DiCaprio gives an all-time career performance. Billy is a South-Boston-based cop who goes undercover to investigate a gang led by Frank Costello (Jack Nicholson). As it turns out, Billy is pretty damn good at playing a fake gangster—but he runs into trouble when the police department is infiltrated by a criminal disguised as a cop.
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Forrest Gump
Set in the fictional town of Greenbow, Alabama, Forrest Gump stars the legendary Tom Hanks as a developmentally delayed boy who, thanks to his mother, doesn’t let it hold him back. As he grows up, Forrest becomes a college football star, is drafted into the Vietnam War, and acclimates into adulthood—all while inspiring others with kindness.
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Parasite
The 2020 Academy Awards sweep heard ‘round the world, Bong Joon-ho’s Parasite is a dark dramedy thriller arguably unmatched in last year’s Oscar race, thanks to its innovative storytelling. Illustrating an ideological meditation on capitalism, the film follows a lower-income family in South Korea as they steadily invade a wealthy family’s home via household jobs.
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12 Years a Slave
Adapted from the 1853 memoir of Solomon Northup, 12 Years a Slave follows Northup’s journey from his birth as a free Black man in New York through his eventual kidnapping and enslavement in 1841. Director Steve McQueen was the first Black filmmaker to ever win Best Picture with this period drama.
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One Flew Over the Cuckoo’s Nest
From Czech New Wave director Miloš Forman, One Flew Over the Cuckoo’s Nest tells the story of one convicted man’s attempt to avoid prison punishment by purposefully transferring to a mental institution.
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Moonlight
No, not La La Land. Best Picture winner Moonlight, directed by Barry Jenkins, has cemented itself as a monumental title in American cinema both for its captivating storytelling and gripping subject matter. The film follows Chiron, a Black gay man, from his childhood in Miami to his adulthood, as he struggles with his identity.
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The Godfather
Arguably the most acclaimed title from the godfather of film himself, Francis Ford Coppola, The Godfather is the first installment of the American crime trilogy based on Mario Puzo’s novel of the same name. The film’s star-studded ensemble portrays the family of mafia boss Vito Corleone, whose “family business” is in the midst of being passed down to his isolated son.
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Slumdog Millionaire
Danny Boyle’s iconic Slumdog Millionaire tags along with Jamal Malik, a young man whose life journey from the slums of Mumbai leads him to the hot spot on Who Wants to Be a Millionaire?
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Schindler’s List
From the brilliant mind of Steven Spielberg, Schindler’s List retells the heroic life of Oskar Schindler, a Sudeten German man who used his work as a businessman in WWII-era Poland to save over a thousand Jewish people from the Holocaust.
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The Silence of the Lambs
In the still-chilling The Silence of the Lambs, Jodie Foster stars as a young FBI trainee who is assigned to investigate a serial killer with torturous methods of killing women. She must seek an unlikely mentor in the imprisoned, cannibalistic serial killer Hannibal Lecter in order to properly understand her suspect.
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On the Waterfront
After all these years, On the Waterfront is one of the most iconic winners in Academy Awards history. Marlon Brando stars as a dockworker determined to dismantle the corruption on the Hoboken waterfront by testifying against the wrongdoings of the industry’s mob boss.
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It Happened One Night
In the true rom-com style of beloved American filmmaker Frank Capra, It Happened One Night is the screwball, yet sensible story of one young woman’s disobedient evasion from her stifling father and journey to love. Disgruntled by his daughter’s recent marriage, the father takes off with her on his yacht. However, when she jumps ship, she washes up with her sights upon new horizons… and an unexpected lover.
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Kramer vs. Kramer
Before Meryl Streep and Dustin Hoffman were two of the most notable names in Hollywood, the duo were Ted and Joanna Kramer: a New York City couple facing the harsh trials of lost love in this heart-wrenching story of their custody battle. If Marriage Story pulled on your heartstrings, this classic will rip them out.
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West Side Story
Scored by Leonard Bernstein with lyrics from Stephen Sondheim, Broadway adaptation West Side Story is the peak of musical cinema. A modern-day spin on Romeo and Juliet, the musical follows the romance of Maria, a Puerto Rican immigrant, and Tony, a white American in the rival gang of Maria’s family and friends. Amidst battles between the Sharks and the Jets, Maria and Tony battle for their right to love in peace.
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Casablanca
Often lauded as one of the greatest and most referenced films in history, Casablanca stars Humphrey Bogart as an American expatriate residing in the Morroccan city of Casablanca during World War II. When his old flame, played by Ingrid Bergman, comes back into town with her new husband, a Czech resistance leader, the expat must make the sacrifice of deciding whether to aid the couple in their escape from the city.
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The Lord of the Rings: Return of the King
Our modern-day Wizard of Oz, Peter Jackson's adaptation of the fantasy classic is a masterclass in epic storytelling. With unparalleled special effects, touching performances, and large-scale battle sequences, The Lord of the Rings: Return of the King took home Best Picture for the entirety of this nine-hour trilogy. It was also the first fantasy film to ever receive the Academy's highest honor.
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No Country For Old Men
For filmmakers as beloved and acclaimed as Ethan Coen and Joel Coen, it is high praise to say No Country For Old Men is their greatest achievement so far. The pitch-perfect adaptation of Cormac McCarthy's novel of the same name is a modern American classic. Along with Best Picture and Best Director(s), Javier Bardem was the first Spanish actor to win Best Supporting Actor, for his role of the terrifying assassin Anton Chigurh.
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