The greatest films to win Best Picture at the Oscars, from Gone With The Wind to Parasite

Hollywood just wouldn’t be Hollywood without the Oscars — and just in the nick of time, this year's ceremony proved why.

The win for Parasite is the Academy's answer to a public tired of predictable wins and a lack of diversity. The 2020 nominations were most notable for who was left out: only one person of colour picked up a nomination in the acting categories, while no female directors got the nod.

Clearly then, they might not always get it right — but since 1929, the Academy Awards have been committed to celebrating the greatest films ever made.

And while the Best Picture choices can be divisive — you won’t find 1999’s Shakespeare In Love, 2006’s Crash or controversial 2019 winner Green Book anywhere near this list — it's still by far the most significant award in film, and arguably even popular culture as a whole.

From legendary movies of the 40s and 50s, right up to contemporary classics, these are the greatest Oscar winners of all time.

Gone With The Wind set the blueprint for the countless dramas of Hollywood’s Golden Age that followed: a couple embark on a passionate but turbulent relationship, with things ending in tumultuous circumstances. It might be a familiar formula, but Gone With The Wind has never been matched for emotional poignancy. Vivien Leigh and Clark Gable are peerless in the 1939 classic, whichs plays out against the backdrop of the American Civil War.

Although the Oscars began more than a decade previously, Gone With the Wind is one of the the first winners still widely celebrated by mainstream audiences today, though the film’s attitudes to race are undoubtedly deeply problematic — New York Post critic Lou Lumenick is just one to criticise the film for romanticising slavery, called for it to be banned in 2015.

In 1939 though, the thoughts of the Academy were well aligned with popular opinion. As well as being lauded by critics, it was the biggest commercial success of its time, with its box office takings coming in at around $393m — £3.4 billion when adjusted for inflation. One of the biggest success stories at the Awards at the time, it took the prize for Outstanding Production, Best Director for Victor Fleming, Best Supporting Actress for Hattie McDaniel and Best Adapted Screenplay.

Even seven decades on from its release, the chemistry of Humphrey Bogart and Ingrid Bergman in Casablanca has yet to be matched in Hollywood. The pair’s aching, on-off romance is as turbulent as the film’s war-torn backdrop, and beautifully realised by two actors at the absolute peak of their powers. From the first moment they're seen together on screen, the viewer buys into the couple’s past, present and future — whatever that may be.

Casablanca manages to be sweeping and grandiose in its outlook, while also capturing a searing romantic intimacy. It is rightly regarded as of the defining movies of Hollywood’s golden age and one of the most enduring love stories in film. Fans have also got the incredible screenplay to thank for some of the most quotable moments in film history — “Of all the gin joints in all the towns…”, “Here’s looking at you, kid” and “Louis, I think this is the beginning of a beautiful friendship” to name but a few.

The decision to eschew a cliched happy ending have helped the film’s legacy live on too. The heartbreaking final scenes gave the movie whole new layer of pathos, ensuring it could never be pigeonholed as just another doe-eyed romance from the war.

All About Eve marked a breakthrough for the Academy in 1950, becoming the first movie with a predominantly female cast to win Best Picture.

The film, which follows the insidious relationship between a fading Broadway star and a younger fan, features a career-best performance from Bette Davis. She’s fabulous as leading lady Margo Channing, who begins to fear the threat of Anne Baxter’s superfan Eve Harrington after allowing her into her inner circle.

The movie also features one of the earliest performances from Marilyn Monroe — an unknown at the time, who would go on to breakthrough with Gentlemen Prefer Blondes a few years later.

After making his name with films like The Lost Weekend in 1945 and Sunset Boulevard in 1950, Billy Wilder turned in two of the greatest romantic comedies ever made in the space of a year; Some Like It Hot and The Apartment.

In many ways, the Best Picture-winning latter is the perfect movie: there are tears and laughter in equal measure, with a tenderness that never tips over into sentimentality. Jack Lemmon is brilliant as extorted businessman CC "Bud" Baxter, who falls for Shirley MacLaine’s Fran Kubelik in unfortunate circumstances. The actor was integral to the success of both Some Like It Hot and the Apartment, expertly treading the line between comedy and tragedy and developing a wonderful chemistry with the excellent MacLaine. It’s an ineffably beautiful film, which just proves that comedies don’t always get overlooked at the Oscars.

Some of the most stunning choreography ever put to screen can be found in Lawrence of Arabia, an epic historical drama from director David Lean. Peter O’Toole delivered a star-making performance as the titular TE Lawrence, the British Lieutenant who played a key role during the British army’s Sinai and Palestine campaigns of WWI. Omar Sharif is also fabulous as Hashemite Arab leader Sherif Ali, who developed great on-screen chemistry with O'Toole.

It’s breathtaking in its scale, mixing technical achievement, grandiose staging and choreography with intimate character studies. The film is a towering achievement of cinema, with O’Toole — possessor of the most striking blue eyes in cinema — right at the heart of its success.

The Godfather is so synonymous with greatness, it’s sometimes taken for granted just how close to cinematic perfection the film gets.

The incredible cinematography and atmosphere of the piece is testament Francis Ford Coppola's position as one of the leading filmmakers in Hollywood history — something he’d go on to prove with Apocalypse Now four years later.

Coppola’s masterpiece features a host of powerhouse performances from the likes of Robert Duvall, James Caan, and not least Marlon Brando — who Coppola had to fight hard to cast in the film at the time, following a string of disappointing roles and a controversial performance in Last Tango in Paris. Talia Shire, Diane Keaton and John Cazale are also superb, while the movie marked Al Pacino as one of the finest actors of his generation.

The movie picked up Best Picture, as well as Best Adapted Screenplay and Best Actor for Brando. The Godfather II followed, famously becoming the only sequel to ever win the Best Picture Oscar.

Jack Nicholson was on the most charismatic form of his career in this adaptation of Ken Kesey’s novel One Flew Over the Cuckoo’s Nest. The film takes a nuanced look at mental illness, exploring power dynamics in an Oregon psychiatric hospital and the draconian conditions inmates are kept in.

Nicholson plays repeat offender Randle McMurphy, who is moved to the institution from prison and encounters the tyrannical Nurse Ratched — one of the most subtly unnerving movie villains ever, played to perfection by Louise Fletcher.

The movie was as hilarious at it was harrowing, and despite strong competition from Dog Day Afternoon and Jaws, its brilliance was recognised with Oscars for Best Picture, Lead Actor, Lead Actress, Best Director and Best Adapted Screenplay.

Jonathan Demme’s unforgettable Silence of the Lambs became only the third film ever to win the big five Oscars at the 1992 ceremony: Best Picture, Lead Actor, Lead Actress, Best Director and Best Adapted Screenplay. It Happened One Night and One Flew Over The Cuckoo’s Nest were the only films to have managed it before.

Jodie Foster brought a fascinating mix of strength, intelligence and vulnerability to the role of prodigious FBI trainee Clarice Starling, forming one of cinema’s finest odd couple relationships with Anthony Hopkins’s Hannibal Lecter. Hopkins, at the peak of his powers, brought just enough pantomime camp and grandeur, as well as fantastic physicality to the role.

It’s also one of the most quotable movies ever made, which holds up spectacularly well nearly 30 years on. It’s also easy to forget how much the film defied Oscars convention at the time. The Academy has long been reluctant to recognise horror in the Best Picture category – movies as visceral and as violent as The Silence of the Lambs often fail to win recognition at the Awards, which makes its success all the more remarkable.

Steve McQueen received the Oscars recognition he deserved in 2013, following his powerful films Hunger and Shame a few years earlier. 12 Years A Slave rightly won Best Picture at the Academy Awards in 2014, which marked one of the strongest years for the category in recent times — Dallas Buyers Club, American Hustle, Nebraska, Captain Phillips, Gravity, Her, Philomena and The Wolf of Wall Street were also nominated.

The film tells the story of Solomon Northup, a free man subject to unimaginable horrors after being separated from his family and sold into slavery. The movie is staggering in scale and ambition, and features one of the most impressive ensemble casts of the decade so far. There are fantastic performances from the likes of Lupita Nyong’o, Paul Dano, Paul Giamatti, Benedict Cumberbatch, Sarah Paulson and Brad Pitt, as well as the beautiful, stoic performance from Chiwetel Ejiofor in the lead role. The Academy also recognised the tyrannical performance from McQueen’s long-term collaborator Michael Fassbender as slave owner Edwin Epps with a Best Supporting Actor nomination.

Barry Jenkins announced himself as a leading filmmaker of his generation with Moonlight — the stunning, semi-autobiographical tale of a young black man growing up on the poverty-stricken streets of Miami, discovering his identity and sexuality in the most testing of circumstances. The beautiful coming-of-age tale is told in three distinct time periods, starring three different actors in the main protagonist role. The effect is astonishing — few films have ever tackled the subjects of masculinity and sexuality so eloquently.

The film will, inevitably, be associated with the infamous La La Land/Oscars envelope debacle at the 2017 ceremony, but this timeless piece of filmmaking should be remembered as one of the most awe inspiring movies of the 21st century.

The win of Moonlight looked, for a moment, to be a double-edged sword: on the one hand, it proved the Oscars could be progressive and inclusive. On the other, the win offered the Academy an easy rebuttal to criticisms over a lack of representation. Parasite's win feels weightier. It stands as the first-ever foreign language film to win Best Film — though it picked up International Feature film too, grasping the double win that eluded Roma in 2019 — and it's an utterly deserved win: this is the Academy doing more than trying to swat away the critics.

South Korean master Bong Joon-ho, known for his work on Okja and Snowpiercer, has created one of the most remarkable pieces of filmmaking of recent times, which has transcended genre and language to win rave reviews everywhere. Set in Seoul, it follows two opposing families, one rich and one poor; to watch their relationship unravels is a remarkable thing. A visceral powerhouse, the way the narrative is constructed is uniquely insidious, gripping and moving, while performances across the board are flawless, making this surely one of the best ensemble pieces of recent times. It is a bold and thrilling watch and, as the Standard's David Sexton wrote in his five-star review: "it freely overrides any genre categorisation, now seeming social realism, now almost Brian Rix-style farce, then thriller, then horror or fantasy, without ever being confined by any of them."

“Once you overcome the one-inch-tall barrier of subtitles, you will be introduced to so many more amazing films,” Bong had said, ahead of the Oscars. This incredible piece of filmmaking is testament to that – the director may have just single handedly opened up film fans to incredible experiences from all over the world. That, alone, is worth celebrating.