95 Years of Oscars: Ranking the Best Picture Winners Part Three – #50-26

Welcome to Part Three of our four-part series on “95 Years of Oscars: Ranking the Best Picture Winners!” In this installment, we dive into a collection of films that have been recognized as the best of the best, occupying positions 50 to 26. From renowned classics to contemporary masterpieces, join us on a journey through Academy history as we explore the cinematic achievements that have left a lasting impact on the industry. With a focus on exceptional storytelling, outstanding performances, and exquisite craftsmanship, these Best Picture winners have solidified their place in the chronicles of film history.

This segment of the list contains a collection of films that might be viewed as controversial. While acknowledging the controversies surrounding some of the filmmakers and actors involved, I still find it easy to appreciate the artistic achievements and storytelling prowess of these Best Picture winners. I hope that you respect that I can, just as I respect if you cannot. I assure you, our personal opinions can coexist. With that said, I hope you enjoy this curated selection of films that have shaped the landscape of cinema, continue to reverberate with audiences worldwide, and celebrate the power of movies – all while acknowledging the complexities of navigating the relationship between art and artist.

You can find Part One (95-76) here and Part Two (75-51) here.

50. Birdman or (The Unexpected Virtue of Ignorance) (2014)
Summary: Alejandro Gonzalez Iñárritu made one of the most deranged and ambitious films to ever win Best Picture. Detractors might argue it is a tad pretentious, but haters be damned. Michael Keaton is incredible as the washed-up, disillusioned actor hoping a Broadway play will revive his career. The black comedy plays on an irreverent version of Keaton’s own career while being a wholly original satire on Hollywood, celebrity, and movie superheroes.
What it beat: American Sniper, Boyhood, The Grand Budapest Hotel, The Imitation Game, Selma, The Theory of Everything, Whiplash
Hindsight’s a bitch: The Academy got this right. Wes Anderson’s Budapest Hotel and Damien Chazelle’s Whiplash would have been equally deserving winners.

49. Marty (1955)
Summary: Ernest Borgnine delivers a masterful portrayal off a lonely and self-doubting bachelor, whose quest for happiness becomes an endearing exploration. Marty, written by the great Paddy Chayefsky, not only earned Borgnine an Oscar but also holds the distinction of being the first film to win both the Cannes Palme d’Or and the Academy Award, a feat only paralleled by Parasite in 2019. Clocking in at a concise 94-minutes, it remains the shortest duration ever for a Best Picture winner.
What it beat: Love Is a Many-Splendored Thing, Mister Roberts, Picnic, The Rose Tattoo
Hindsight’s a bitch: Hard to argue against such a profound character study of the everyday man. As much as I love Marty, James Dean gave us two films in 1955 that could be used to argue against it winning. Rebel Without a Cause is the one I would give the prize to, with East of Eden being another strong film for the short-lived icon. Alfred Hitchcock’s To Catch a Thief and Charles Laughton’s The Night of the Hunter are two thrillers from 1955 that have left quite a legacy. Some good choices, and Marty isn’t a bad one.

48. Slumdog Millionaire (2008)
Summary: Danny Boyle’s enchanting Slumdog Millionaire stands as one of the most remarkable success stories in the history of the Academy Awards. This little gem was destined for obscurity (it almost went straight to video) before it burst onto the scene, captivating audiences and leaving an indelible mark on the awards circuit. With a heartwarming love story at the center, the film follows the extraordinary path of a poor Indian boy who transcends the slums and finds himself on the Indian iteration of Who Wants to Be a Millionaire. Each question becomes a poignant link to his quest for reunion with his childhood sweetheart. Admittedly, the narrative can be unapologetically sentimental, but Boyle and his team execute it with such finesse that it becomes impossible not to embrace this tender film.
What it beat: The Curious Case of Benjamin Button, Frost/Nixon, Milk, The Reader
Hindsight’s a bitch: This was the last time we had the simple, pedigreed five nominees for Best Picture. The notable absence of Christopher Nolan’s The Dark Knight, the second installment in his Batman trilogy, played a significant role in pressuring the Academy to broaden the nomination field. This expansion aimed to provide a fairer opportunity for high-profile, blockbuster films to compete for Oscar recognition. I am in total alignment with Slumdog’s victory, and am against the era of expansion.

47. The English Patient (1996)
Summary: Speaking of amazing love stories… from sweeping vistas, incredible performances, and one incredible score, Anthony Minghella’s The English Patient is one of the most beautiful films to ever win the Best Picture Oscar. Spanning many years and several countries (behold the allure of the African desert sands), the love affair of two star-crossed lovers is told through flashbacks as a mysterious burnt man lies dying in an old Italian monastery. He recounts his woeful tale to his young, wide-eyed nurse. The incredible cast includes Ralph Fiennes, Juliette Binoche, Willem Dafoe, Naveen Andrews, and Colin Firth.
What it beat: Fargo, Jerry Maguire, Secrets & Lies, Shine
Hindsight’s a bitch: The English Patient has been unceremoniously pushed aside since winning nine Academy Awards. The film suffers from beating another movie that most individuals prefer over the Academy’s choice – The Coen Brothers’ Fargo. Fargo remains a terrific film that has stood the test of time admirably. While I can appreciate those who champion its idiosyncratic and brilliantly unconventional narrative set in the north, I personally align wholeheartedly with the Oscars’ choice to honor Minghella’s evocative and emotionally charged tale.

46. The Last Emperor (1987)
Summary: Bernardo Bertolucci’s film is groundbreaking from at least one standpoint: it was the first movie ever allowed to be shot in Beijing’s Forbidden City. The Last Emperor is an awe-inspiring telling of Puyi’s life – from governing a nation as a child to his imprisonment as a man. The Last Emperor is a gorgeously shot, decade-spanning biopic with an international cast and an incredible propensity to recreate the Qing Dynasty China era. It’s one of those films I admire more each time I view it.
What it beat: Broadcast News, Fatal Attraction, Hope and Glory, Moonstruck
Hindsight’s a bitch: While there are a few movies I would rank ahead of Bertolucci’s lush and grand film, I in no way fault the Academy for this selection. In fact, I think it was a very brave and commendable selection. My pick for the best film of 1987 would go to Stanley Kubrick’s Vietnam drama, Full Metal Jacket. Having gone with Platoon – Oliver Stone’s take on the Vietnam War – the prior year, it is no surprise that the Academy turned away from a similar theme just one year later. It’s a shame they couldn’t find room for it as a nominee, though.

45. American Beauty (1999)
Summary: American Beauty stands as an undeniably divisive and polarizing film that delves into the complexities of a dysfunctional suburban family. While it enjoyed immense popularity in 1999, subsequent analysis has scrutinized its controversial themes and the actions of its lead actor. Acknowledging the challenging nature of watching it today, given the allegations against Kevin Spacey, some viewers still manage to appreciate the film’s inherent beauty and separate it from the artist. With its clever and thought-provoking exploration of middle-class life, American Beauty continues to ignite conversations and debates, setting it apart from many other films further down the list.
What it beat: The Cider House Rules, The Green Mile, The Insider, The Sixth Sense
Hindsight’s a bitch: Among cinephiles, if you were to inquire about the greatest year in film, 1999 would undoubtedly rank high on many lists. The other nominees alone serve as compelling evidence. While my personal preference of the five nominees lies with The Matrix, Stanley Kubrick once again demonstrates his mastery of film, directing the film that I believe deserved the accolade: the haunting and provocative erotic thriller, Eyes Wide Shut.

44. 12 Years a Slave (2013)
Summary: Steve McQueen’s adaptation of Solomon Northup’s memoir is a searing and thought-provoking portrait of pre-Civil War American slavery. Solomon is played with aching realism by Chiwetel Ejiofor, and he is surrounded by an incredible cast that delivers exceptional performances. From Michael Fassbender’s steely and menacing turn as the slave owner, to Lupita Nyong’o’s heart-wrenching breakthrough performance as one of the slaves, 12 Years a Slave is an absorbing and divinely crafted film, even if it is a brutal watch.
What it beat: American Hustle, Captain Phillips, Dallas Buyers Club, Gravity, Her, Nebraska, Philomena, The Wolf of Wall Street
Hindsight’s a bitch: Like many films at this point on the list, I make no qualms about 12 Years a Slave’s victory. It was an important, powerful, and tremendous movie. My pick would have been for Alfonso Cuarón’s Gravity, which is one of the most immersive and nerve-racking films I have ever sat through. Not since the storming of Omaha Beach in Saving Private Ryan have I been that stuck to the edge of my seat. Captivating visuals, substantial themes, and cutting-edge technologically made Gravity one of the five best films of the decade.

43. Patton (1970)
Summary: There are few single images from film that are more iconic than the one pictured above. George C. Scott delivers an unparalleled performance, embodying “Old Blood and Guts” himself, General George S. Patton. Capturing the immense fury and audacious hubris of the titular role, Scott – the fantastic bastard that he was – famously refused the Oscar for Best Actor. Directed by Franklin J. Schaffner and co-written by Francis Ford Coppola, Patton remains one of the great war films for the fact that it can be conceived and both patriotic and anti-war in its delivery.
What it beat: Airport, Five Easy Pieces, Love Story, M*A*S*H
Hindsight’s a bitch: The Academy got this right.

42. Forrest Gump (1994)
Summary: Speaking of iconic performances, Tom Hanks as Forrest Gump is one for the ages. Robert Zemeckis’ film is an enchanting and nostalgic view of one man’s inconceivable journey through life. Gump is an endearing and enduring character, even if the extraordinary path is too far-fetched for the cynical mind. Sit back and try not to overthink this fanciful tale and you might just get soaked up in its wistful charm.
What it beat: Four Weddings and a Funeral, Pulp Fiction, Quiz Show, The Shawshank Redemption
Hindsight’s a bitch: It’s a pretty incredible year when you have at least three films that would make for an outstanding Best Picture winner! Do I agree with Forrest Gump winning? I have no problem with it. My vote would enthusiastically go to Pulp Fiction (or even The Shawshank Redemption, perhaps), but I won’t deny that at the time I was rooting for Gump to win the prize.

41. The Sting (1973)
Summary: George Roy Hill’s The Sting is one of the all-time great crowd-pleasers to ever win Best Picture. Robert Redford, Paul Newman, Robert Shaw, Charles Durning, and Eileen Brenan make for a hell of a playful cast. The film is full of elaborate double-crossings, delightful shenanigans, and nostalgic ragtime-era costumes and music. The Sting epitomized the perfect blend of amiability and accessibility, making it a prime example of what it used to take to craft an Oscar-winning film.
What it beat: American Graffiti, Cries and Whispers, The Exorcist, A Touch of Class
Hindsight’s a bitch: If it is in the 70s, then you know it was an incredible year. Along with The Sting, 1973 gave us George Lucas’ American Graffiti, Franklin J. Schaffner’s Papillon, Sidney Lumet’s Serpico, Martin Scorsese’s Mean Streets, Terrence Malick’s Badlands, Sydney Pollack’s The Way We Were, and Robert Clouse’s Kung-Fu classic, Enter the Dragon. But it is William Friedkin’s The Exorcist that would have been my choice. The scariest movie of all-time is also an incredibly well acted film, and one that still haunts me with each viewing.

40. In the Heat of the Night (1967)
Summary: Norman Jewison’s crime thriller, In the Heat of the Night, stars Sidney Poitier as Virgil Tibbs, a Philadelphia detective who travels south and ends up helping solve a murder. As usual, Poitier lights up the screen with dignity and grace as he works through racial bigotry. The small town of Sparta, Mississippi features a police department led by Chief Gillespie (Rod Steiger), a man slow to adapt to the changing times who is clearly outmatched by Tibbs. The pair act out an odd couple partnership as they work to solve the crime, and in the process, they learn to form a mutual respect for each other.
What it beat: Bonnie and Clyde, Doctor Doolittle, The Graduate, Guess Who’s Coming to Dinner
Hindsight’s a bitch: In the Heat of the Night is a terrific time capsule of a film, coming out amidst the Civil Rights movement of the 1960s. While a fine choice, The Graduate would have been an even better winner. Great year for film, once again.

39. Gladiator (2000)
Summary: Ridley Scott might not have won the Oscar for Best Director, but his Ancient Roman swords-and-sandals epic took home five Oscars, including Best Picture of 2000. Russell Crowe won the Oscar for playing Maximus, a Roman General turned imprisoned gladiator when he is betrayed by the King’s son, Commodus (played with ingratiating contempt by Joaquin Phoenix). This is one of the last big-budget, grandiose Hollywood blockbusters to win Best Picture, as most of the next two decades would be flooded with arthouse cinema champions.
What it beat: Chocolat, Crouching Tiger, Hidden Dragon, Erin Brokovich, Traffic
Hindsight’s a bitch: Gladiator would have been my second choice and is an amazing winner either way. But Ang Lee’s Crouching Tiger, Hidden Dragon is among my favorite movies ever made. With breathtaking martial arts battles, majestic backdrops, and extraordinary storytelling, Crouching Tiger is a monumental film and a marvel for the eyes.

38. Spotlight (2015)
Summary: Tom McCarthy’s Spotlight details the Boston Globe’s Pulitzer Prize-winning attempt to uncover an appalling, decades-long child-abuse scandal within the Catholic Church. The big movie to play at my first Telluride Film Festival, I will never forget the power the film possessed on our audience. As the credits rolled, grown men around me began openly weeping. It’s not just that it is a profound story, but one that is executed to perfection that draws out such emotion.
What it beat: The Big Short, Bridge of Spies, Brooklyn, Mad Max: Fury Road, The Martian, The Revenant, Room
Hindsight’s a bitch: Hard to beat a news journalism story this thorough, far-reaching, and well executed (perhaps only All the President’s Men did it better). The Academy got this one correct.

37. Parasite (2019)
Summary: Parasite’s win was a landmark moment for the Academy: it was the first non-English language film to win Best Picture. Bong Joon Ho’s many-sided, dark social satire is a cunning and resourceful commentary on South Korea’s economic inequality. Why it works is the relevance of that system across societies of every nation, and that, to paraphrase Casablanca, makes Parasite a citizen of the world.
What it beat: Ford v Ferrari, The Irishman, Jojo Rabbit, Joker, Little Women, Marriage Story, 1917, Once Upon a Time… in Hollywood
Hindsight’s a bitch: While Parasite is more than deserving of the Best Picture title, I would have preferred to see Sam Mendes’ World War I masterpiece 1917 win out on the night.

36. Rebecca (1940)
Summary: Adapted from Daphne du Maurier’s dark and thrilling novel, Rebecca is Alfred Hitchcock’s only Best Picture winner. As the new, second wife of aristocrat Maxim De Winter (Laurence Olivier), Joan Fontaine can’t escape the lingering specter of his dead wife, kept alive by the unhinged and domineering housekeeper, Mrs. Danvers (Judith Anderson). Mysterious and suspenseful, Rebecca is a mentally and psychologically stimulating experience.
What it beat: All This, and Heaven Too, Foreign Correspondent, The Grapes of Wrath, The Great Dictator, Kitty Foyle, The Letter, The Long Voyage Home, Our Town, The Philadelphia Story
Hindsight’s a bitch: Who would take the Oscar away from the only Hitchcock winner? Not me, though John Ford’s The Grapes of Wrath is the real MVP of 1940.

35. It Happened One Night (1934)
Summary: Few comedies have won Best Picture, and even fewer are more deserving than Frank Capra’s cultured and risqué (at the time) movie, It Happened One Night. In what is essentially a quaint and hysterical road movie, Peter Warne (Clark Gable) is an unemployed journalist who finds the next big story covering Ellie (Claudette Colbert), a spoiled heiress who is running from the man she left her marriage for only to try to return to the man she was originally married to, and somehow along the way ends up falling for the disgruntled reporter as they travel across the country. Get all that? Satisfying and romantic, the chemistry between Gable and Colbert is unmatched.
What it beat: The Barretts of Wimpole Street, Cleopatra, Flirtation Walk, The Gay Divorcee, Here Comes the Navy, The House of Rothschild, Imitation of Life, One Night of Love, The Thin Man, Viva Villa!, The White Parade
Hindsight’s a bitch: The Academy undoubtedly got this one right.

34. Moonlight (2016)
Summary: There are very few coming-of-age films that are more delicate, intimate, and utterly bewitching than Barry Jenkins’ Moonlight. And just as memorable as the heart-wrenching story is, the night it won is even more memorable. A blunderous misreading of the incorrect envelope for Best Picture allowed for the wrong movie to be called out. This left the La La Land producers to figure out the error and announce the real winner on stage to a dumbfounded and awestruck audience.
What it beat: Arrival, Fences, Hacksaw Ridge, Hell or High Water, Hidden Figures, La La Land, Lion, Manchester by the Sea
Hindsight’s a bitch: 2016 remains one of my favorite film years thanks in part to the magnificent quartet we had at Telluride. Along with Moonlight, other films that played to rapturous applause included La La Land, Arrival, and Manchester by the Sea. As profoundly moving and beautifully told as Moonlight is, I couldn’t help but fall for Damien Chazelle’s masterwork, La La Land. The bittersweet and enchanting film is nostalgic of a world that seems to have vanished. Full of dazzling song-and-dance numbers, vivid and vibrant color palettes, and one of the most heartbreaking and genuinely accomplished climaxes in the history of cinema, La La Land was my favorite movie of the decade.

33. The Hurt Locker (2009)
Summary: Kathryn Bigelow became the first female to win Best Director as her Iraq War film, The Hurt Locker, won Best Picture. Intense as it was timely, Bigelow’s film follows a bomb-disposal unit that is in constant danger, an adrenalin rush that Staff Sergeant William James (Jeremy Renner) has become viciously addicted to. Evocative and unsettling, The Hurt Locker remains an outstanding and cautionary war drama.
What it beat: Avatar, The Blind Side, District 9, An Education, Inglourious Basterds, Precious, A Serious Man, Up, Up in the Air
Hindsight’s a bitch: As much as I love The Hurt Locker, my vote would have gone to Quentin Tarantino’s Inglourious Basterds, which might be the director’s most audacious and violent film to date. Beyond the savage brutality is a highly entertaining tale of retribution featuring one of the most dastardly villains audiences have ever endured, Nazi Gestapo Col. Hans Landa (Christoph Waltz).

32. Dances with Wolves (1990)
Summary: As a Civil War veteran, John Dunbar (Kevin Costner) wants to see the American frontier before it disappears. Along the way, he unexpectedly befriends a Lakota Sioux tribe and takes on the dilemma the Native Americans were facing as the country expanded west. Costner produced, directed, and starred in Dances with Wolves, an exquisitely shot Western epic with majestic landscapes detailing the crimes against indigenous people and the final years of the American West.
What it beat: Awakenings, Ghost, The Godfather Part III, Goodfellas
Hindsight’s a bitch: Unfairly remembered more for what it beat than how gorgeous a film it is, Dances with Wolves is a film I will die on this hill for. I believe it holds up among the best movies ever made, even if Martin Scorsese’s Goodfellas is the superior of the two. Sure, Marty deserved this win, but don’t let that take away from the fact that Dances with Wolves is a truly magnificent film.

31. An American in Paris (1951)
Summary: Vincente Minnelli’s dreamlike musical, An American in Paris, paired the catchy tunes of George and Ira Gershwin with the electric charisma of Gene Kelly. The result is a mesmerizing and romantic anecdote that climaxes with a dazzling and exuberant 17-minute ballet sequence featuring Kelly and Leslie Caron that was radical at the time and iconic to this day.
What it beat: Decision Before Dawn, A Place in the Sun, Quo Vadis, A Streetcar Named Desire
Hindsight’s a bitch: While one of my favorite winners, An American in Paris is overshadowed by another nominee that year, Elia Kazan’s explosive adaptation of Tennessee Williams’ A Streetcar Named Desire. Featuring the greatest acting quartet in film history, Streetcar is an actor’s smorgasbord, feasted upon with searing delight by Marlon Brando, Vivien Leigh, Karl Malden, and Kim Hunter.

30. From Here to Eternity (1953)
Summary: Frank Sinatra, Montgomery Clift, Deborah Kerr, Burt Lancaster, Ernest Borgnine, and Donna Reed lead an all-star cast in Fred Zinnemann’s From Here to Eternity. The 1953 Best Picture-winner depicts the lives of the soldiers stationed in Hawaii in the weeks before the Japanese attack on Pearl Harbor. The hopes and dreams of romance are overshadowed by the inevitable attack that only the audience knows is coming. Remembered best for its dreamy and iconic beach scene, From Here to Eternity was ahead of its time in the way it tackled topics of sex and infidelity.
What it beat: Julius Caesar, The Robe, Roman Holiday, Shane
Hindsight’s a bitch: I love Shane, but the Academy got it right with From Here to Eternity.

29. The Departed (2006)
Summary: Finally, Martin Scorsese wins! One of the best crime dramas ever made, The Departed is a riveting film capable of being watched repeatedly. The pacing, acting, and writing are all superb, but what did you expect from a Scorsese picture? Full of violence, corruption, and duplicity, The Departed stars Jack Nicholson as a mob boss, Leonardo DiCaprio as an undercover cop, and Matt Damon as the mob’s mole.
What it beat: Babel, Letters From Iwo Jima, Little Miss Sunshine, The Queen
Hindsight’s a bitch: Some might argue that Scorsese finally won for The Departed to right the wrongs of his past losses. While this isn’t one of his four or five best films, that notion is utter nonsense. Few have a resumé anywhere near Scorsese’s. The Departed was not only the best film of 2006, but it also stands as one of the best movies to ever win Best Picture.

28. Unforgiven (1992)
Summary: There are few actors more iconic for a genre than Clint Eastwood is for the Western. Unforgiven is his best film – both as an actor and director – and chronicles the American West like few films had done before. Haunted by his violent past, Eastwood’s anti-hero – the notorious William Munny – saddles up for one last ride in this Best Picture-winning tale of vengeance and retribution. The way Munny and his old friend, Ned Logan (Morgan Freeman), talk about their past is haunting and unusual for a genre that has typically glorified violence. David Webb Peoples’ screenplay skillfully balances the seasoned perspective on the ramifications of violence with the compelling journey of a young gunslinger determined to make a name for himself. The result is a truly thought-provoking experience.
What it beat: The Crying Game, A Few Good Men, Howards End, Scent of a Woman
Hindsight’s a bitch: The Academy got this correct.

27. Titanic (1997)
Summary: One of three films to tie for the record of winning 11 Oscars, James Cameron’s account of the Titanic is as colossal as the ship itself. The first half of the film invests you in the characters aboard the unsinkable ship, notably a budding and unlikely romance between Jack (Leonardo DiCaprio), a poor artist in steerage, and Rose (Kate Winslet), a rich debutante born into first class. The way Cameron gets us to care about their relationship – some cheesy lines aside – despite the predetermined knowledge of the doomed, historic disaster is what makes the second half of the film that much more nail-bitingly delicious. Whether or not Jack could have fit on the door with Rose is beside the point. The fact that we still watch the film 26 years later hoping she will make room for him – that is the stuff of magic.
What it beat: As Good as It Gets, The Full Monty, Good Will Hunting, L.A. Confidential
Hindsight’s a bitch: Cheesy lines and lack of a Screenplay nomination aside, the Academy got this correct.

26. Platoon (1986)
Summary: Drawing on his own sorrowful experiences in the Vietnam War, Oliver Stone’s Platoon is heralded as one of the most visceral and authentic war films ever made. Platoon stands as a resolute examination of the atrocities of war, serving as a poignant portrayal of the demise of American idealism and the tragic consequences of deploying young men and women into combat. Its enduring relevance remains striking, reminding us of the timeless horrors associated with the armed conflict.
What it beat: Children of a Lesser God, Hannah and Her Sisters, The Mission, A Room with a View
Hindsight’s a bitch: The Academy got this correct.

As we conclude Part Three of our four-part series on “95 Years of Oscars: Ranking the Best Picture Winners,” we have examined a rich assortment of films that have etched their names in Oscar history. While some of these films have been embroiled in controversy or faced criticism for triumphing over others, it is important to recognize their artistic achievements and their ability to captivate audiences, which led to their recognition by the Academy.

Looking ahead to Part Four, I am eager to dive into the top 25 Best Picture winners, an exclusive collection of films that remain timeless classics. Join us next week for the final installment of our series, when we will continue our journey through the Oscar-winning films and unveil the crème de la crème of Best Picture winners.