The 25 best Oscar-winning movies you should watch before you die

Gem Seddon
·15 min read
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Every year, the best and brightest of Hollywood meet together at one star-studded event to celebrate their greatest achievements. We are, of course, talking about the Academy Awards, better known as the Oscars.

They are, as intended, a great barometer for sorting the good movies from the bad. But choosing the best Oscar-winning movies of all time is quite a challenge. There have been almost 100 ceremonies since the award's inception, and each one gives prizes to a couple of dozen movies. 

So, how did we come up with this list? We only looked at those movies that won the prestigious Best Picture award and then chose our favourites from that list. So, without further ado, here are the 25 best Oscar-winning movies you should watch before you die. 

25. The Deer Hunter (1978)

Talk about bleak victories... Michael Cimino's Vietnam drama may not be an uplifting film, but that's partly why it struck a chord with the Academy. One of only a few films to directly address the effects of the war, it's a striking piece of cinema that cuts between the delight of American soldiers enlisting and the horrors they face once they're at war.

The Deer Hunter's a haunting epic that boasts a stellar cast – led by Robert De Niro at the peak of his acting powers – and has the Russian roulette scene to end all Russian roulette scenes.

24. West Side Story (1961)

Is West Side Story the best musical of all time? Since its release, plenty of competitors have emerged, but there's something infectious about the sheer energy of the movie. A Romeo and Juliet story told in New York City's west side through the medium of song and dance – its as fun as you might expect. 

Think Grease but with way smoother collar-poppin'. Plus, afterwards, you won't be able to stop clicking your fingers and telling people to just be cool. No wonder Steven Spielberg wanted to remake this classic.

23. Unforgiven (1992)

You know how it goes. A cop on the verge of retirement is dragged into a life-changing case on his last day. Clint Eastwood's 1992 western, Unforgiven, takes that idea and yanks it through the dust and grime of Big Whisky, a small town that's witnessed some heinous activities.

At the top of his game, both in front and behind the camera, Eastwood gives one of his best performances as the grizzled – is he ever anything else? – William Munny, an outlaw who returns to finish one last job. It's still a surprise that such a dark, violent fable managed to bag the Oscar.

22. Moonlight (2016)

There are few movies as heart-wrenching as Moonlight, a movie split into three distinct acts, each one focussing on a different time period in the main character's life. With three different actors portraying Chiron/Black/Little, this could have been a tonal mess. But under Barry Jenkins' masterful touch, each one works in perfect tandem with the other. 

The result is perhaps the most emotional Oscar winner of the 21st century. Watching Chiron come of age while struggling to comprehend his own sexuality is heartbreaking. Then there's his strained relationship with his mother, played beautifully by Naomie Harris. Have tissues on standby. 

21. Amadeus (1984)

Still lingering over Milos Forman's film is the small matter of accuracy. What actually went down between Wolfgang Amadeus Mozart and his noted rivals? Was it really this soap opera-ish? It's not the first biopic to dally with the truth, and that shouldn't make a difference when the movie itself is this much of a majestic experience. 

Tom Hulce tackles the part of the classical composer, displaying lots of restraint considering Mozart's reputation as a larger-than-life character. Miloš Forman's direction is also excellent and makes this almost three-hour movie breeze by.

20. The Hurt Locker (2009)

Before playing Hawkeye in the MCU, Jeremy Renner played William James in Kathryn Bigelow's Iraq drama, The Hurt Locker. As a war-savvy vet, Renner's Sergeant First Class heads up an explosive ordnance disposal team in Baghdad, eventually going off-mission to seek revenge for the murder of a young boy.

It's through his maverick and often dangerous methods that the movie opens up its larger theme; how conflict truly affects soldiers. Plus, it's the first Best Picture winner directed by a woman.

19. On The Waterfront (1954)

Based on the real-life story of a New Jersey whistleblower, this tale of corruption at the docks made Marlon Brando into a bona fide star. He also bagged his first Oscar as longshoreman Terry Malloy, a conflicted soul who stands up against the mob-controlled union despite his own shortcomings.

Sure, he's most fondly remembered for The Godfather, but this put him on the map. The movie also earned director Elia Kazan his second Oscar and introduced Eva Marie Saint to the world.

18. No Country For Old Men (2007)

One of the Coen brothers' most ambitious efforts, No Country for Old Men plays like an updated western, ripe with dark, seedy undertones setting the scene for one hell of a mystery. Seeing as this is a Coen film, the story is told through the experiences of a regular joe who opts to completely ruin his life.

Josh Brolin plays Llewelyn Moss, the man in question, who discovers a bag of cash and decides, "I'll keep it! Why the hell not?" Javier Bardem's bolt gun-wielding psychopath Anton Chigurh answers that question for him, as one of cinema's most menacing and fearsome villains.

17. The Bridge on the River Kwai (1957)

David Lean directs this excellent World War Two movie, reimagining the brutal enslavement of Allied prisoners forced to build the Burma railway. Alec Guinness' British Colonel encourages his soldiers to help the Japanese with the bridge as a way of boosting morale, while a fellow Brit pushes William Holden's American officer to destroy the bridge upon completion.

It exposes the truth behind Japanese Prisoner of War camps, and how thin the line between heroism and loyalty really is. Guinness is excellent as the Brit with the stiff upper lip, giving an all-time great performance.

16. Rocky (1976)

Sylvester Stallone wrote and directed his breakout role in Rocky. Like his on-screen counterpart, he too rose like the Philadelphian underdog who dreams of boxing in the heavyweight championship.

Rocky became the highest-grossing of the year, bagging $225 million, and turned Stallone into a global star. From his determination to succeed to his ambitious, post-montage air-punch at the top of the museum steps, you can't help but root for Rocky to bag that title.

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15. Lord of the Rings: Return of the King (2003)

There was no way the Academy could ignore Peter Jackson's Tolkien trilogy. A visually-adventurous tale of Hobbits, Elves, Orcs and – above all – the true strength of friendship, it was a travesty that the previous two movies didn't scoop up awards.

With an A-list cast, attention to detail, and respect towards the source novels, The Return of the Kings benefitted from voters who realised, third time around, just how groundbreaking this trilogy was. 

14. It Happened One Night (1934)

It Happened One Night was a trailblazer, paving the way for the modern romantic comedy as we now know it. Before Frank Capra's screwball caper, there were no amusing scenarios for when couples first meet in movies or scenes where characters dissect their heartbreak with their friends.

All of that stems from the story of Claudette Colbert's hoity heiress, who finds herself torn between two suitors, and goes for the least likely option. It Happened One Night took the conventions of the post-Depression era, when women were in pursuit of financial security, and twisted them into something fresh.

13. Midnight Cowboy (1969)

"I'm walking here!" yells Dustin Hoffman's scam artist as a New York City cab nearly mows him down. It's a scene that's so iconic it almost overshadows the movie itself, which is worth noting because Hoffman improvised the line. John Schlesinger's ease for letting his drifter picture go wherever his leads liked is part of what makes it feel so natural.

The story follows Jon Voight's Joe Buck. After leaving Texas for the bright lights of the big city, he turns tricks to make a living and, along the way, befriends Ratso (Hoffman). The first X-rated movie to ever win Best Picture. By today's ratings, it would be an NC-17 – the UK equivalent of an 18.

12. One Flew Over the Cuckoo's Nest (1975)

Miles Forman's adaptation of Ken Kesey's novel is a classic for a reason. In possibly his best performance, Jack Nicholson plays Randle McMurphy, a wise-cracking con artist who talks his way into a mental institution to forgo a harsher prison term. He rages against the machine that's run by the evil Nurse Ratched (Louise Fletcher) and befriends all sorts of folks inside, including a pre-Doc Brown Christopher Lloyd. 

It'll uplift your soul and break your heart in equal measure, and the fact that it's so good at doing both justifies every award that's been thrown at One Flew Over the Cuckoo's Nest. 

11. Gone With the Wind (1939)

A grand, majestic picture that walked away with eight Oscars, Gone With the Wind remains a cornerstone of cinema. That this lush melodramatic tale of romance and injustice during the American Civil War even made it to the big screen remains a mini-miracle.

The movie was beset with problems right throughout its lengthy production, from the hundreds of actresses who tested for the part of Scarlett O'Hara to the sheer quantity of directors who came and went. Adapted from Margaret Mitchell's novel, it's still the most successful movie in box office history when adjusted for inflation.

10. Schindler's List (1993)

Steven Spielberg's has made dozens of palatable blockbusters out of dozens of mismatched topics. Aliens, spies, and robots – you name it, Spielberg's probably made a movie about it. For Schindler's List, the filmmaker tackles a more serious subject than normal, crafting an evocative, powerful movie based on a historical event that saw 6 million Jews senselessly murdered.

Despite garnering negative attention while making the movie, Spielberg nevertheless chose to focus his movie on the 600 people who survived the Holocaust thanks to Oskar Schindler (Liam Neeson). It's unashamedly a Spielbergian take on things, putting the spotlight on the decency of man even in our darkest hours.

9. The Apartment (1960)

Well-known at the time for screwball comedies, Billy Wilder tried something new with The Apartment. It became an instant game-changer – a pioneering example of what Hollywood could get away with.

Jack Lemmon stars as Baxter, an insurance agent who lets his office pals use his apartment to entertain their mistresses, all the while struggling to find love himself. that is, of course, until he meets Shirley Maclaine's whip-smart elevator operator, Fran. It's her performance that's the real turning point. She's full of biting wit and self-deprecating one-liners, yet still brings an edge of darkness to Baxter's humdrum life.

8. The French Connection (1971)

Dom Toretto's crew have got nothing on the petrolhead prowess of Gene Hackman in The French Connection. As Detective Jimmy Doyle he might pursue justice behind the safety of a badge, but there's nothing remotely by-the-book about his swaggering determination.

Tasked with bringing down a ring of heroin smugglers in New York City, he embarks on one of the best car chases ever filmed. The unrelenting demands of director William Friedkin saw a large portion of the city's subway shut down for the scene, in which Hackman's cop hurtles around the streets in his Pontiac to pursue his train-bound target.

7. Annie Hall (1977)

One of Woody Allen's best romantic comedies saw the director turn away from the weird, oddball pictures he was making and dive into something more mainstream. Casting Diane Keaton as the title character was a masterstroke. Carefree and cool, and with trend-setting fashion sense, she's the perfect antidote to Allen's neurotic Alvy Singer.

Their funniest moment happens while they discuss their next date, as a series of captions appear to illustrate the differences between what we say and what we mean. While he wasn't the first director to break the fourth wall, he's the one who wrung the most laughs from its possibilities.

6. The Godfather (1972)

Based on Mario Puzo's novel, The Godfather gave birth to the modern mobster movie. Its influence over the entire gangster genre spilled out into real life, with New York City's crime lords taking their cues from the Corleone family. 

So much from the movie has been lifted into pop culture via spoofs and parodies: the horse head in the bed, the mutterings of Marlon Brando's wiseguy, and that sweet piece of improvised dialogue, "Leave the gun. Take the cannoli." It's perhaps no wonder that many people regard the movie as perhaps the best movie of all time.

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5. Silence of the Lambs (1990)

Since when did serial killer movies that include poetic cannibals and skin-wearing psychopaths win Oscars? That's what's so impressive about Jonathan Demme's movie. It's rare for a genre movie to win anything, never mind the Best Picture, but Silence of the Lambs beat its competitors in every single nominated category.

What clinched it? The dynamite script, utterly haunting score, and mesmerising turns from Jodie Foster and Anthony Hopkins? It's all of those things, and that tightly-edited final sequence, which remains just as chilling as the stuff you'll see in any horror movie worth its salt.

4. All About Eve (1952)

The double-whammy of Bette Davis as veteran actress Margo Channing and Anne Baxter as her conniving ingenue Eve Harrington is what makes All About Eve still so watchable. The pair are flung together in this timeless story about our resistance to growing old, with Davis' scathing delivery of Joseph L. Mankiewicz's razor-sharp dialogue making this her finest performance.

"Fasten your seatbelts, it's going to be a bumpy night", says Channing, unaware that the perils of ambition without decency might require a little more Dutch courage.

3. Lawrence of Arabia (1962)

There are few movies that define spectacle cinema like David Lean's sprawling Lawrence of Arabia, which went on to inspire a generation of filmmakers – notably both Spielberg and George Lucas hold the movie as one of their favourites.

Lawrence of Arabia's cinematography is gorgeous, and Peter O'Toole plays World War One officer T.E. Laurence perfectly, managing to balance both arrogance and heartfelt sympathy for the people the British are invading. More impressive than its thousands of extras is the movie's length; at 227 minutes, it remains the longest movie to ever take home the Best Picture trophy. A true epic. 

2. Casablanca (1943)

Casablanca's the great American movie. A brilliant blend of romance, thriller, and war-torn actioner that has two top-of-their-game actors in leading roles. Whatever you want to call it, you can't deny the watchability of Michael Curtiz's World War Two adventure, which sees Humphrey Bogart and Ingrid Bergman as two lovers who can't be together.

Chemistry like theirs is rarely seen onscreen nowadays, a result of their off-set friendship which also gave the film its most memorable one-liner. In between takes, Bogart would teach his co-star poker, often repeating the phrase, "Heres looking at you, kid" to Bergman out of genuine affection.

1. The Godfather: Part II (1974)

Themes of loyalty, family, and sacrifice drive home Francis Ford Coppola's second chapter in the Corleone clan's tale. One of the first sequels ever to outdo its predecessor, the movie surges with confidence. Coppola takes everything that made the first movie jolt moviegoers out of their seats, and ups the stakes.

Part II takes a look back through the early years of Vito Corleone in Sicily, charting his accomplishments before he became the New York City mafioso. Robert De Niro joins the cast as the young Don, alongside Al Pacino in the greatest gangster movie ever made.