A few years ago, I set out to watch every Best Picture winner dating back to The Godfather (1972). For some odd reason, after completing that monumental and occasionally boring task, I felt the need to become a true Oscar historian and watch them all. Forty-four movies later, I can say that I have. Essentially, I watched The Greatest Show on Earth so you wouldn’t have to. Without further ado:
95. Cimarron (1931)
Cimarron was the first Western to win Best Picture, and one of only four Westerns to ever win the award (the others being Dances With Wolves, Unforgiven, and No Country For Old Men). Cimarron may also be the only Best Picture winner without a single redeeming quality. Decades later, the movie is close to unwatchable, chock full of glaringly racist stereotypes.
What should’ve won: M
94. Driving Miss Daisy (1989)
Driving Miss Daisy isn’t bad—okay, it’s bad.
What should’ve won: Do the Right Thing
93. Crash (2005)
I took the easy way out when discussing the racial politics behind Driving Miss Daisy. There simply isn’t much for me to say that hasn’t already been said more eloquently. Crash is the clumsiest handling of race relations imaginable. It’s closer to parody than reality.
Crash was doubly insulting because its win represents one of the three worst Oscar snubs of all time. Brokeback Mountain is one of the best films of the century.
What should’ve won: Brokeback Mountain
92. The Greatest Show on Earth (1952)
Cecil B. DeMille’s showy circus drama is often regarded as one of the worst Best Picture winners ever, so its place here should come as no surprise. The Greatest Show on Earth may have been selected to reward DeMille for his illustrious career, because it was the safest choice during the Red Scare, or simply because the Academy sometimes selects terrible winners.
What should’ve won: Singin’ in the Rain
91. You Can’t Take It with You (1938)
Unsurprisingly, Frank Capra’s 1938 comedy didn’t lack charm, but instances of repulsive racial stereotypes make it borderline unwatchable. Fortunately for Capra, two of his other films, It Happened One Night and Mr. Smith Goes to Washington, are easier to stomach and more beloved.
What should’ve won: Bringing Up Baby
90. The Great Ziegfeld (1936)
MGM used The Great Ziegfeld as a Trojan horse for spectacle. The Academy has a mixed track record when it comes to rewarding style over substance (The Greatest Show on Earth, yes, Avatar, mercifully, no). The Great Ziegfeld probably could’ve been an interesting biopic about a Broadway producer, but it turned into an extravagant three-hour musical. Did I mention that it also has blackface?
What should’ve won: Modern Times
89. Gigi (1958)
The movies on this list are being evaluated as films first and foremost, but it’s hard to ignore crass or offensive content. Gigi isn’t the worst musical to ever win Best Picture, but it is the most problematic. One tune called “Thank Heaven for Little Girls” hasn’t aged well.
What should’ve won: Vertigo
88. Out of Africa (1985)
The movie features Meryl Streep, Robert Redford, and some nearly pornographic shots of Nairobi, but Sydney Pollack’s two hour and 40-minute slog stands as not only one of the worst Best Picture winners to date, but also one of the worst films I’ve ever seen. A romance starring Streep and Redford seems like an easy sell until you learn Redford’s character is a big-game hunter, a profession that Out of Africa is quick to glorify. From a modern perspective, big game hunting has never been less sexy.
What should’ve won: Ran
87. Going My Way (1944)
Should you separate the art from the artist? The ongoing debate intensified in the era of Louis C.K. and Woody Allen, and we’re no closer to a definitive answer. Going My Way’s lessons are harder to swallow now, as this otherwise cheery movie now comes off as preachy and hypocritical with Bing Crosby as its face. Even if you’re able to see Going My Way for what it was intended to be, the film won Oscars thanks to Crosby’s star power.
What should’ve won: Double Indemnity
86. Green Book (2018)
Winners like 12 Years a Slave and Moonlight pointed to change amongst Academy members, but Green Book‘s victory is a reminder that progress isn’t always a straight line. Similar thinking led to the selection of the naive Driving Miss Daisy over Spike Lee’s smoldering Do the Right Thing. After being relentlessly mocked for 30 years for that decision, the Academy should’ve known better.
What should’ve won: Minding the Gap
85. Cavalcade (1933)
Cavalcade is the original Forrest Gump: its characters pinball through life, careening from one historic event to the next. The characters don’t instigate the Watergate investigation, but they do experience the Second Boer War, Queen Victoria’s funeral procession, the sinking of the Titanic, and World War I. There’s little plot to connect the events, making Cavalcade forgettable at best.
What should’ve won: 42nd Street
84. The Broadway Melody (1929)
The first musical and the first talkie to win Best Picture, The Broadway Melody must’ve been quite a spectacle for audiences and the Academy alike. My choice for Best Picture, Alibi, was released as a silent film and sound film simultaneously. 1929 was a transition year for the industry, but that doesn’t excuse The Broadway Melody, which looks pedestrian compared to its contemporaries.
What should’ve won: Alibi
83. The Life of Emile Zola (1937)
The Life of Emile Zola is stronger in concept than execution. For those rusty on late 19th century French history, the script follows Emile Zola, a prominent Jewish figure who testified in court to exonerate Alfred Dreyfus, a wrongfully convicted Jewish man. Though its runtime is under two hours, the movie feels a full three. In recent years, the film has sparked some controversy about whether or not Warner Bros. demanded that all mentions of the word Jew were to be removed from the script.
What should’ve won: Make Way for Tomorrow
82. Around the World in 80 Days (1956)
Around the World in 80 Days is an all-time Academy headscratcher. Long before the first travel television show, I reason that Around the World won on the back of stunning vistas and remarkable places that people weren’t as inundated with as we are today. The Jules Verne novel its based on is just over 150 pages long. Despite that, the movie tops out at nearly three hours. The script desperately needed an editor.
What should’ve won: The Searchers
81. The Artist (2011)
2011 was a relatively weak movie year, and yet it’s unfathomable that The Artist won Best Picture. Hugo, which celebrates the same aspects of classic Hollywood cinema as The Artist, is a better crafted and more enjoyable movie. The cynic in me always viewed The Artist as a movie made to win awards, and with Harvey Weinstein there to push it across the finish line, it was successful in its pursuit.
What should’ve won: Melancholia
80. Chariots of Fire (1981)
I have a dirty little secret to admit: I’m a sports fan who hates sports movies. The best sports movies, like biopics, are character studies hidden behind the veil of a momentous story. Although Chariots of Fire accomplished that, it shouldn’t have been enough to stave off Raiders of the Lost Ark.
What should’ve won: Blow Out
79. Gone with the Wind (1939)
Gone with the Wind is ranked this highly in recognition of its technical mastery. With a runtime nearing four hours, Gone with the Wind’s scale is truly staggering. Outside of those accomplishments, the movie is troubling. Its story is deeply sympathetic to the Confederate South, and worse yet, it glorifies marital rape and slavery. When people name it as their favorite movie, I can’t help but shoot them a sidewards glance.
What should’ve won: The Wizard of Oz
78. Oliver! (1968)
Regardless of whether you think 2001: A Space Odyssey is a sci-fi masterstroke for the ages or a pretentious, convoluted pile of garbage, we can all agree that it had a greater impact than Oliver! over the last half-century. Astoundingly, 1968 also featured Night of the Living Dead, the original Planet of the Apes, Once Upon a Time in the West, Bullitt, and Rosemary’s Baby. When ranking the best films of 1968, Oliver! probably doesn’t crack the top 10.
What should’ve won: 2001: A Space Odyssey
77. The King’s Speech (2010)
Occasionally, Academy voters are given the ability to vote for a movie that defines an era. Nothing could’ve done that better than The Social Network, a film about the nature of startups, social media, and internet culture. Instead, the Academy opted for a British period piece.
What should’ve won: The Social Network
76. Gentleman’s Agreement (1947)
Just years after the Holocaust, Gentleman’s Agreement attempted to shed light on everyday anti-semitism. It did, in its own awkward way.
Miracle on 34th Street, a better film, was also nominated for Best Picture in 1947. It wasn’t the only Christmas movie to be nominated, either. The Bishop’s Wife also received the nod.
What should’ve won: Miracle on 34th Street
75. Tom Jones (1963)
Tom Jones is a wonky, forgettable winner. If you like breaking the fourth wall as often as possible, then Tom Jones checks that box. It also features a scene where the titular Tom Jones and a woman who is likely his mother shall we say, uh, provocatively share a meal. So that’s something.
What should’ve won: 8½
74. Grand Hotel (1932)
Grand Hotel is the only Best Picture winner that did not receive a nomination in any other category. It may not work as a movie, but it serves as an interesting who’s who of the era, featuring Greta Garbo, John Barrymore, and Joan Crawford.
What should’ve won: Shanghai Express
73. Gandhi (1982)
Tootsie, E.T. the Extra-Terrestrial, The Thing, and Blade Runner were all better movies with more cultural significance than Richard Attenborough’s endless Gandhi biopic. 1982 is one of the best examples of the disconnect between the audience and Academy voters.
What should’ve won: Blade Runner
72. Mutiny on the Bounty (1935)
Based on a historical event and a novel, Mutiny on the Bounty has been adapted to film four times. Part romance, part courtroom drama, Mutiny is adequate but undeserving of its cult status.
What should’ve won: Mutiny on the Bounty
71. CODA (2021)
CODA is yet another example of the Academy placing sentiment and good feelings ahead of depth and innovation.
What should’ve won: Drive My Car or The Power of the Dog
70. Dances With Wolves (1990)
Some of the best movies of the 20th century were Westerns. You wouldn’t know it based on the Academy’s choices.
What should’ve won: Goodfellas
69. Hamlet (1948)
Laurence Olivier cut Shakespeare’s (best) play in the interest of saving time. His film suffers for it.
What should’ve won: The Treasure of the Sierra Madre
68. A Beautiful Mind (2001)
A Beautiful Mind was both historically and medically incorrect, which, even for a movie, is an impressive feat. Hayao Miyazaki’s Spirited Away was the best movie of the year, but an animated foreign film will never win Best Picture. That leaves The Lord of the Rings: The Fellowship of the Ring, Donnie Darko, Mulholland Drive, Memento, Training Day, Ocean’s Eleven, and Gosford Park. Knowing that LOTR will sweep in two years, I’ll take Mulholland Drive.
What should’ve won: Mulholland Drive
67. Slumdog Millionaire (2008)
Slumdog Millionaire is a good movie that had no place in the Oscar conversation. The film’s tone is perplexing considering the life-threatening reality of poverty.
What should’ve won: Milk
66. Argo (2012)
Argo‘s win over Steven Spielberg’s Lincoln is puzzling. Biopics are right up the Academy’s alley and Lincoln may also be the best performance of Daniel Day-Lewis’s career. Bizarre.
What should’ve won: Lincoln
65. Shakespeare in Love (1998)
Saving Private Ryan, The Big Lebowski, and American History X all should’ve won Best Picture before Shakespeare in Love was considered, but the movie is better than its reputation. Detractors are bound to pan your film when it participates in one of the worst Oscar upsets in history.
What should’ve won: Saving Private Ryan
64. West Side Story (1961)
West Side Story is a Shakespearean melodrama propelled forward by an endless list of showstoppers. While it may be a classic, it isn’t a good movie.
The Academy rarely awards foreign films the honor of Best Picture nominations, but my choice would’ve been Akira Kurosawa’s Yojimbo. It may not be as grandiose as Kurosawa’s Seven Samurai, or as revelatory as his Rashomon, but Yojimbo would’ve had a better argument for Best Picture against West Side Story than his other masterpieces would’ve against On the Waterfront or All About Eve, respectively. Besides, directors rarely win for their best films. Ask Martin Scorsese.
What should’ve won: Yojimbo
63. Ben-Hur (1959)
Unfortunately, the spat between star Charlton Heston and co-writer Gore Vidal over Ben-Hur’s subtextual homoeroticism is more entertaining than Ben-Hur itself. Besides, Gladiator‘s chariot races were better.
What should’ve won: Some Like It Hot
62. Mrs. Miniver (1942)
Mrs. Miniver is about the impacts of World War II, set, filmed, and released in the heat of the war. Sadly, it was a lackluster winner in a lackluster year in film. Sometimes the field is stacked to the point that deserving winners aren’t nominated, and other times the field is so weak that the best choice is still a bad one. This was the latter.
What should’ve won: Yankee Doodle Dandy
61. How Green Was My Valley (1941)
Citizen Kane remains one of the most influential movies ever made. Decades later, Citizen Kane can be appreciated as a technological marvel. Meanwhile, Jeopardy! fans will recognize How Green Was My Valley as Alex Trebek’s favorite movie.
What should’ve won: Citizen Kane
60. Wings (1928)
The only fully silent movie to ever win Best Picture, Wings is notably better than you’d expect. Wings features the melodramatic acting and extreme sentimentality that plagued films of the era, but its combat scenes and camera work were well ahead of its time. Film students are more likely to study Fritz Lang’s revolutionary Metropolis, but the first Best Picture winner was a deserving one.
What should’ve won: Metropolis
59. All the King’s Men (1949)
All the King’s Men hadn’t aged well until a certain Willie Stark-like character won a national election. As time went by, it seemed less and less likely that we could elect a demagogue in the information age, when more people than ever are educated. Of course, like all great cautionary tales, we completely ignored All the King’s Men.
What should’ve won: All the King’s Men
58. Annie Hall (1977)
There’s no bigger debate about separating the art from the artist than with Woody Allen. Annie Hall is a hallmark comedy, but it’s not my bag. In fact, even doing my best to separate Allen’s life from his work, I’ve always found him generally unfunny. Annie Hall‘s immense following is responsible for its place on the list.
My choice is another prestige blockbuster. No science fiction movie has ever won Best Picture. Between Blade Runner, 2001: A Space Odyssey, and Close Encounters of the Third Kind, that’s a travesty.
What should’ve won: Close Encounters of the Third Kind
57. The Last Emperor (1987)
Picturesque cinematography makes The Last Emperor worth watching. The slow two hour and 43-minute runtime makes it worth skipping.
What should’ve won: Broadcast News
56. Rain Man (1988)
Autism is a delicate subject to cover, and while Rain Man deserves blame for its inaccuracies, it also deserves praise for raising awareness about the condition. Believe it or not, Rain Man was the highest-grossing movie of 1988.
What should’ve won: Cinema Paradiso
55. Terms of Endearment (1983)
The ‘80s were a relatively poor decade for prestige pictures. Terms of Endearment, though clever and moving, is evidence of that. Big performances from the likes of Jeff Daniels, Shirley MacLaine, and Jack Nicholson provide the film with endearing qualities, but it’s fair to describe the movie as “emotionally manipulative.”
What should’ve won: Terms of Endearment
54. Forrest Gump (1994)
Pulp Fiction and The Shawshank Redemption are two of my five favorite movies, so I’ll try not to make this personal. Forrest Gump is a movie that I like less every year. For one, we’ve all seen it two million times (admittedly not its fault). Worse though, it feels more like a fairy tale than the cultural examination it strives to be. Forrest Gump skirts around subjects like AIDS without ever veering close enough to say something interesting.
What should’ve won: Pulp Fiction
53. My Fair Lady (1964)
The musical adaptation of George Bernard Shaw’s Pygmalion is a delight. Audrey Hepburn was tremendous as Eliza Doolittle, but that shouldn’t have been enough to take the top prize away from Dr. Strangelove, a movie as funny and damning today as the day it was released. Best Picture wasn’t the only award My Fair Lady stole from Dr. Strangelove; egregiously, the Academy also awarded Rex Harrison Best Actor over Peter Sellers.
What should’ve won: Dr. Strangelove
52. American Beauty (1999)
Does anyone have strong feelings about this suburban satire? Years after seeing American Beauty, I still couldn’t tell you what it was trying to say.
What should’ve won: The Matrix or Eyes Wide Shut
51. A Man for All Seasons (1966)
Seven of the 10 Best Picture winners from the ’60s were period pieces. A Man for All Seasons is one. Following the trend, it’s good, if not a little boring.
What should’ve won: Who’s Afraid of Virginia Woolf?
50. Marty (1955)
Ernest Borgnine’s exceptional performance as a lovable loser stabilizes Marty’s weakest aspect: its dialogue.
What should’ve won: The Night of the Hunter
49. The Hurt Locker (2009)
Kathryn Bigelow’s Iraq War thriller is a tense work of art. As good as The Hurt Locker is, though, it makes you wonder if Quentin Tarantino will ever secure a Best Picture win. If Tarantino couldn’t win for Reservoir Dogs, Pulp Fiction, or Inglourious Basterds, it’s hard to imagine him winning at all. The opening scene of Inglourious Basterds is one of the most suspenseful scenes on film.
What should’ve won: Inglourious Basterds
48. Nomadland (2020)
Chloé Zhao’s meditation on work, loss, and the American West doesn’t have the depth of The Rider, her previous feature. What’s there is beautiful, but it will leave you wanting.
What should’ve won: The Father
47. Everything Everywhere All at Once (2022)
When you make it past the hotdog fingers, dildo fights, and existential rocks, EEAAO is relatively conventional Oscar fare; it’s a family drama with a saccharine ending. Everything Everywhere separates itself by leaning into genre filmmaking, generational trauma, and the immigrant experience.
What should’ve won: Tár
46. Chicago (2002)
Chicago shouldn’t have won Best Picture, but it sure is spectacular.
What should’ve won: City of God
45. The English Patient (1996)
Fargo may be the proper winner, but The English Patient is an ageless love story. Ralph Fiennes and Kristin Scott Thomas both put on splendid performances, and the shockingly somber ending helps to separate it from other romance films. It doesn’t hurt that Ralph Fiennes is unbelievably handsome.
What should’ve won: Fargo
44. Braveheart (1995)
Would you believe me if I told you a Mel Gibson movie was bloated, self-important, and preachy? Braveheart is epic, but it’s not without its problems. Seven, Heat, and Apollo 13 were all better films. Only Apollo 13 was nominated.
What should’ve won: Seven
43. From Here to Eternity (1953)
Featuring a few career-best performances, From Here to Eternity was a smash success at the box office. A few subplots, though, including one about a boxing tournament, don’t land all of their punches.
What should’ve won: Tokyo Story
42. The Shape of Water (2017)
If a Guillermo del Toro movie was going to win Best Picture, most would agree that the director’s dark fairytale, Pan’s Labyrinth, should’ve been the choice. Although The Shape of Water isn’t del Toro’s best work, its unique production design, practically-realized fish-monster costume, and weird plot serve as a breath of fresh air (or a spritz of Amazonian water) among the Academy’s usual fare.
What should’ve won: Get Out
41. Midnight Cowboy (1969)
Midnight Cowboy has some interesting things to say about New York City and sex, but it’s bleak to the point of deep cynicism.
What should’ve won: Midnight Cowboy
40. Rocky (1976)
An early scene between Rocky and Adrian ends in what can only be described as date rape. Rocky would find itself much higher on the list if not for that mishap.
What should’ve won: Network
39. Million Dollar Baby (2004)
Ranking Million Dollar Baby above Rocky feels blasphemous, but don’t blame me, Raging Bull didn’t even win Best Picture.
What should’ve won: Eternal Sunshine of the Spotless Mind
38. The Best Years of Our Lives (1946)
William Wyler’s classic about soldiers returning home from war stands the test of time. The film came at an important time, too, released one year after the end of World War II.
What should’ve won: The Best Years of Our Lives
37. The Lost Weekend (1945)
Depending on who you talk to, The Lost Weekend either qualifies as an oversimplification of addiction or a movie ahead of its time. You can guess which camp I fall in.
What should’ve won: Brief Encounter
36. Titanic (1997)
Titanic is an entire generation’s favorite movie. That has to count for something.
What should’ve won: Titanic
35. An American in Paris (1951)
Gene Kelly’s introduction to Leslie Caron absolutely does not pass for anything but creepy today, but I can’t help ranking this one a little too high. It oozes Golden Age Hollywood charm, and, in my opinion, is better than Singin’ in the Rain.
What should’ve won: A Streetcar Named Desire
34. Birdman or (The Unexpected Virtue of Ignorance) (2014)
Birdman has become a divisive Best Picture winner in short order. Alejandro Iñárritu’s film catalog is a source of frustration for many, and ambiguous endings like Birdman’s only help to fuel that rage. Initially, I was pleased by the Academy’s selection of Birdman, but upon further reflection, I wish Whiplash had won. Damien Chazelle’s directorial debut is flawless.
What should’ve won: Whiplash
33. The Sound of Music (1965)
The best of four musicals to win Best Picture in the ’60s (My Fair Lady, Oliver!, and West Side Story), The Sound of Music holds up. Dr. Zhivago has received greater appreciation from the film community in the intervening 50 years, but I’m not sure it tops the von Trapp family adventures.
What should’ve won: The Sound of Music
32. Patton (1970)
Patton is a war movie and a biopic, but more than that, it’s a philosophical musing about the life of a romantic poet and military historian. The movie was co-written by Francis Ford Coppola in his prime, and it shows.
What should’ve won: Patton
31. Kramer vs. Kramer (1979)
As a child of divorced parents, I’m legally obligated to rank this one higher than it should be. Kramer vs. Kramer is a decent film, but fairly or not, its legacy will always be denying the best Vietnam war movie (and perhaps the best war movie, period) a golden statue.
What should’ve won: Apocalypse Now
30. The Deer Hunter (1978)
This will be a head scratcher for some. After years of hype, perhaps I went into The Deer Hunter with my expectations set too high. The Deer Hunter is a disjointed film that hones in on the devastation of war. It fully realizes its vision of the devastation of war, but so do about 20 other movies on this list. Still, it was an important movie about Vietnam released only three years after the war’s conclusion.
What should’ve won: The Deer Hunter
29. The Departed (2006)
Preposterously, Scorsese’s first win to came from The Departed, a messy, boisterous gangster thriller. The Academy only has itself to blame for waiting so long to award one of the best filmmakers Hollywood has ever seen.
What should’ve won: Children of Men
28. Platoon (1986)
Apocalypse Now is the best Vietnam movie, but Platoon is a close second.
What should’ve won: Platoon
27. The French Connection (1971)
I realize that this may seem low to some, but the absurdly-named Popeye Doyle never should’ve taken the hardware away from Alex and his more-appropriately-absurdly-named droogs.
What should’ve won: A Clockwork Orange
26. The Sting (1973)
The Sting is the Best Picture winner that had the unfortunate honor of being sandwiched between The Godfather and The Godfather Part II. The Sting is a suave ode to old times, but it wasn’t the best film of the year. If the Academy didn’t have such an aversion to horror films, The Exorcist would be a good candidate here. Otherwise, Martin Scorsese’s Mean Streets is the ideal choice.
What should’ve won: Mean Streets
25. Spotlight (2015)
Spotlight was a safe choice. The best film of 2015, Ex Machina, didn’t receive a Best Picture nomination.
What should’ve won: Ex Machina or The Big Short
24. All Quiet on the Western Front (1930)
The third Best Picture winner is a classic. One of the best anti-war films ever made, All Quiet on the Western Front is impressive nearly 100 years later.
What should’ve won: All Quiet on the Western Front
23. Gladiator (2000)
Gladiator may be the purest action movie to ever win Best Picture. The lines between good and evil are a little too easily defined in Ridley Scott’s Roman drama, but epics regularly commit that sin. The best movie of the year was Hong Kong film In the Mood for Love, but a case could be made for Snatch or Traffic. Gladiator isn’t as insulting as it seems, and the movie serves as a career award for Scott.
What should’ve won: In the Mood for Love
22. Amadeus (1984)
Amadeus is such a timeless story about the rivalry between a generational talent and a transcendent talent that you can almost ignore the massive historical inaccuracies.
What should’ve won: Amadeus
21. On the Waterfront (1954)
Marlon Brando carries a movie that, oddly enough, was written in defense of Red Scare snitching.
What should’ve won: Rear Window
20. Ordinary People (1980)
I unabashedly love Ordinary People. I love it so much that I’m not even mad that it beat Raging Bull, the best sports movie ever. I understand that could be viewed as a hypocritical take, especially after denouncing Terms of Endearment for being emotionally manipulative, but I’ll do my best to make the case: Ordinary People was a movie about mental health 19 years before The Sopranos tried to destigmatize therapy. It’s a compelling story that rides superb performances from Donald Sutherland, Timothy Hutton, and Mary Tyler Moore. Trust me, it’s not as bad as advertised.
What should’ve won: Raging Bull
19. It Happened One Night (1934)
The seventh-ever Best Picture winner has no business being this high on the list, but Frank Capra’s screwball comedy is the quintessential rom-com.
What should’ve won: It Happened One Night
18. Rebecca (1940)
Alfred Hitchcock’s only winner, Rebecca, is everything you’d expect from the master of suspense. The worst thing about Rebecca is that it serves as a reminder that Hitchcock was a working director while many of the weakest movies were awarded Best Picture. It’s impossible to comprehend how directors like Hitchcock and Kubrick, decades ahead of their peers, were awarded a combined one Best Picture winner.
What should’ve won: Rebecca
17. 12 Years a Slave (2013)
Three phenomenal films were released in 2013. The Wolf of Wall Street and Inside Llewyn Davis also would’ve cracked this list’s top 20.
What should’ve won: The Wolf of Wall Street
16. In the Heat of the Night (1967)
Up against The Graduate, Doctor Dolittle, Guess Who’s Coming to Dinner, and Bonnie and Clyde, 1967 was a stacked year. While In The Heat of the Night is criticized as cathartic and on the nose, as someone from the South, I think it’s more accurate than most would like to admit. Better yet, Sidney Poitier’s performance as Virgil Tibbs has aged like fine wine.
What should’ve won: In the Heat of the Night
15. The Bridge on the River Kwai (1957)
The Bridge on the River Kwai is more character study than war film, and it’s better for it. I haven’t been able to get its unpredictable 45-minute third act out of my head since I saw it for the first time.
What should’ve won: The Bridge on the River Kwai
14. Casablanca (1943)
As quotable a movie as you’ll find, Casablanca is every bit as good as the hype suggests.
What should’ve won: Casablanca
13. One Flew over the Cuckoo’s Nest (1975)
There would’ve been no shame in picking Jaws, the movie that launched the blockbuster, but I think the Academy got this one right.
What should’ve won: One Flew over the Cuckoo’s Nest
12. Schindler’s List (1993)
Spielberg didn’t win the top prize until 1993, but it was well worth the wait.
What should’ve won: Schindler’s List
11. Unforgiven (1992)
A Few Good Men, Glengarry Glen Ross, and Reservoir Dogs are all extraordinary movies, but the Academy needed to get the stink of its previous Western winners (Cimarron and Dances With Wolves) off of it. For that reason alone, Unforgiven deserved this one.
What should’ve won: Unforgiven
10. The Lord of the Rings: The Return of the King (2003)
Mystic River is really good, but this award couldn’t have gone to any other movie. Peter Jackson and his crew deserved this for adapting the unadaptable, even if the year-long retreat to New Zealand was reward enough.
What should’ve won: The Lord of the Rings: The Return of the King
9. Lawrence of Arabia (1962)
Earlier I mentioned how the best biopics are character studies hidden behind historical events. That’s Lawrence of Arabia to a tee. Freddie Young’s groundbreaking cinematography makes the movie that much more rewatchable.
What should’ve won: Lawrence of Arabia
8. The Apartment (1960)
Billy Wilder, Shirley MacLaine, and Jack Lemmon all had incredible careers. The Apartment may have been the tops for all three of them.
What should’ve won: The Apartment
7. Moonlight (2016)
Moonlight will likely be remembered as the movie that forced the cast and crew of La La Land off the stage after it was incorrectly announced as the winner at the 89th Academy Awards. That’s a damn shame because Barry Jenkins’s second film is one of the best movies of the 21st century.
What should’ve won: Moonlight
6. The Godfather Part II (1974)
In the hottest of all hot takes, I almost picked Chinatown here, but couldn’t. Fun fact: The Godfather Part II was the first American sequel to use numbers in its title. Another fun fact: The Godfather Part II is definitely not as good as The Godfather.
What should’ve won: The Godfather Part II
5. All About Eve (1950)
Sorry, Sunset Boulevard fans, All About Eve was the proper winner. Its commentary about Hollywood and ageism is sadly relevant today.
What should’ve won: All About Eve
4. The Silence of the Lambs (1991)
The Silence of the Lambs is the only horror movie to ever win Best Picture, and I wouldn’t even describe it as a horror movie. Sean Connery was director Jonathan Demme’s first choice as Hannibal Lecter. Can you imagine? Anthony Hopkins was as iconic in the role as an actor can be, and he did it with only 16 minutes of screen time.
What should’ve won: The Silence of the Lambs
3. Parasite (2019)
It took the Academy 92 years to award a foreign-language film Best Picture. Genre chameleon and audience-accessible genius Bong Joon-ho co-wrote (with Han Jin-won) and directed the historic South Korean thriller. The darkly comedic class-war battle is set in Seoul, but there’s a frightening universality to income inequality.
What should’ve won: Parasite
2. The Godfather (1972)
No two ways about it: The Godfather changed cinema forever.
What should’ve won: The Godfather
1. No Country for Old Men (2007)
There are those who say There Will Be Blood should’ve won Best Picture, and even as someone who ranked No Country for Old Men as the best Best Picture winner ever, I won’t argue. Coincidentally, There Will Be Blood would’ve held the same spot on this list. 2007 was one hell of a year.
Michael Clayton, another nominee, was no slouch, either. Zodiac, The Assassination of Jesse James by the Coward Robert Ford, and 3:10 to Yuma weren’t even nominated. In any other year…
No Country, though, is a masterpiece. Joel and Ethan Coen made the best movie adaptation ever, and for my money, a perfect film.
What should’ve won: No Country for Old Men or There Will Be Blood
A Mixed Review 
