The 12 Best Oscar-Winning Movies of All Time
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Every year the Academy anoints a fresh winners' circle, sending a select few home with little gold men that really are kind of like dolls, the more you think about it. Those who say it's an honor just to be nominated are lying, of course. Everyone wants to win! While there are always Oscar losers more than worth a watch, there are enough Oscar winners in the awards' near-hundred-year history to fill up your streaming queue for life.
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In lieu of scrambling to see all the Oscar nominees in any given year, looking back at the awards' history is a timeless pursuit. From sweeping historical dramas and glitzy movie musicals to weepies and scaries, these Oscar winners are the foundation of any cinephile's must-stream list. And for those who've reached the bottom of the barrel on quarantine viewing, this is a list to come back to time and time again — not a single film will disappoint.
2019 Best Picture: Parasite
Director Bong Joon-ho's playful yet bracing tale of haves and have nots is both a visual and narrative marvel. In 2019 Parasite became the first, and hopefully not the last, non-English-language film to win Best Picture. It features superb performances from venerable South Korean actors Song Kang-ho and Cho Yeo-jeong, in a story of survival and the human cost of the wealth disparity. Parasite's piercing social commentary cuts across cultures and is sure to resonate, whether we like it or not, for years to come.
Where to stream: Hulu
2017 Best Picture: Moonlight
This aching and evocative coming of age from director Barry Jenkins also made Oscar history. In 2017 Moonlight became the first film with an all-Black cast, and the first centered on an LGBTQ+ character, to win Best Picture. Separated into three parts, the film follows a boy from Miami as he navigates his identity, including coming to terms with his sexuality. Mahershala Ali took home Best Supporting Actor for his role as the neighborhood mentor; Janelle Monáe also memorably plays the protagonist's mother.
Where to stream: Netflix
2017 Best Foreign Language Film: A Fantastic Woman (Chile)
With a breakout performance from Daniela Vega, A Fantastic Woman tells the story of a woman who is suspected by her lover's family of having a hand in his death after he suffers a sudden brain aneurysm. The film made history as the first Oscar winner to feature a trans storyline with an openly trans actor in the lead role. Vega also became the first openly trans performer to present at the Oscars. All history-making aside, A Fantastic Woman (Una Mujer Fantástica in Spanish) is, well…fantastic — a kinetic, heartbreaking, and inspiring portrait of perseverance.
Where to stream: Amazon
2018 Best Supporting Actress, Regina King: If Beale Street Could Talk
Barry Jenkins' followup to Moonlight remains a bit unsung, but If Beale Street Could Talk is a beautifully rich adaptation of James Baldwin's 1974 novel. The story follows a pair of young lovers (played by Kiki Layne and Stephan James) and the woman's quest to prove her partner innocent of a crime he didn't commit. Regina King, who recently made her feature directing debut with One Night in Miami, won for for her performance as the young man's weary but determined mother. The stacked cast also features Colman Domingo, Teyonah Parris, Diego Luna, Pedro Pascal, and Brian Tyree Henry.
Where to stream: Hulu
2006 Best Supporting Actress, Jennifer Hudson: Dreamgirls
It's easy to forget that a feature film starring Beyoncé basically playing Diana Ross exists, but it truly does! Dreamgirls may not be the absolute pinnacle of movie musicals, but it's still a worthy vehicle for a host of stellar performances. Jennifer Hudson took home Best Supporting Actress, with an award-clinching rendition of the eleven-o-clock number "And I'm Telling You I'm Not Going." Though the same certainly was not true of her performance as Grizabella in Cats, in which she sings "Memory," Hudson will again flex her vocal chops in a clear awards hopeful, as Aretha Franklin in Respect.
Where to stream: Amazon
2002 Best Picture: Chicago
Renée Zellweger and Catherine Zeta-Jones as rival killers vying for fame behind bars may be the only good thing to come of America's prison system. Rob Marshall's big screen adaptation of the juggernaut stage musical (written by legends John Kander, Fred Ebb, and Bob Fosse) is a splashy whirlwind. It captures the seedy glamour of the Jazz Age in a way that may serve as inspiration for a new century's Roaring Twenties. Oh, and in a truly inspired feat of casting, Queen Latifah plays the jailhouse alpha.
Where to stream: Hulu
2000 Best Foreign Language Film: Crouching Tiger, Hidden Dragon (Taiwan)
Fans of Michelle Yeoh know that her history of taking zero prisoners onscreen began decades before her turn as an indomitable mother-in-law-to-be in Crazy Rich Asians. Most American audiences caught their first glimpse of Yeoh and her fierce martial arts skills in Crouching Tiger, Hidden Dragon. Director Ang Lee's stunning warrior action film was showered with Oscar nominations (the most ever for a non-English-language film, at the time), including Best Picture, taking home the gold for Best Foreign Language Film. The swordsman adventure story features three strong leading female characters, including Yeoh's, who resist the constraints of conventional gender roles.
Where to stream: Amazon
1991 Best Picture: The Silence of the Lambs
Considered by some critics to be among the best films of all time, The Silence of the Lambs is one of the rare Best Picture wins that may have faint-hearted viewers crawling up their seats. Director Jonathan Demme's film defies conventional genre, toeing a line between all-out horror and the psychosexual thrillers that ruled the '90s. Jodie Foster stars as a detective who interviews one sadistic and convicted serial killer of women (played by Anthony Hopkins) in order to catch another still on the lam. The film maintains a complicated legacy. Its depiction of a queer-coded villain who wants to literally get under womens' skin has widely been considered damaging to the trans community at best and grossly transphobic at worst. But the conversation it has inspired continues to expand, with some even arguing that the character represents an "empowered monstrocity." It's one you'll have to watch yourself and decide.
Where to stream: Hulu
1998 Best Picture: Shakespeare in Love
Gwenyth Paltrow's powder-pink Ralph Lauren dress — and her Best Actress triumph over Cate Blanchett in Elizabeth — still likely come to mind when anyone thinks of Shakespeare in Love at the Oscars. But the film itself, written by Tom Stoppard and Marc Norman and directed by John Madden, is a drama nerd's dream. It's filled with clever references to the Bard, including cross-dressing, mistaken identity, secret love, and (gulp) a deadly plague. Judi Dench also won her Best Supporting Actress Oscar, as Queen Elizabeth I, in roughly eight minutes. A deep royal curtsy to that.
Where to stream: Hulu
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1983 Best Picture: Terms of Endearment
They don't make good old-fashioned family dramas like they used to — at least, not on the big screen. Shirley MacLaine and Debra Winger play a widowed mother and her daughter who embark on new relationships and see their bond tested over 30 years' time. James L. Brooks' sweeping film, based on the 1975 novel by Larry McMurtry, is tender-hearted with warm humor and knockout performances, including from fellow stars Jack Nicholson, Jeff Daniels, Danny DeVito, and John Lithgow. It's a tried-and-true tearjerker, if and when you feel the need for an emotional release.
Where to stream: Hulu
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1961 Best Picture: West Side Story
West Side Story is a towering classic of the movie musical genre to which few compare. Artful and electrifying, it's Romeo and Juliet on the streets of 1950s New York City, with unforgettable performances from Natalie Wood as Maria and Rita Moreno as her cousin Anita. Moreno will appear in the Steven Spielberg remake on the way, a touching tribute to the original film. There may never be a bad time to imagine dancing in the streets with the exuberance of youth, but now seems like an especially good one.
Where to stream: Amazon
1934 Best Picture: It Happened One Night
A pinnacle of screwball romantic comedy, Frank Capra's 1934 classic set an early high bar for the whole notion of opposites attract. Claudette Colbert plays a spoiled socialite who's fleeing her wealthy, overbearing father back to the husband she married against his paternal wishes, when (of course) she meets a roguish reporter played by Clark Gable, who wants an exclusive on her story. The two make their madcap way from Florida to New York City, falling in love on the road. For its wit, charisma, and impeccable execution, It Happened One Night is as singular as the title suggests.
Where to stream: Amazon
