In conjunction with the upcoming Academy Awards this weekend, I engaged in the daunting task of catching up with every Best Picture winner ever. While there were moments when this task turned out to be a slog (especially at the end, when my excuses for avoiding certain movies started running perilously thin), it was interesting to go through the many different eras of the Academy where I got to see just how the definition of a “prestige picture” has changed and evolved over the ninety years that the Awards have been given out.
And now in a task fraught with futility and bound to stir up disagreements (and calls of the inanity of the author) I will attempt to rank all the winners from the truly atrocious to the movies that actually deserve to be winners of the Oscar. Before we jump right in, let me just state upfront that these rankings are my opinion and mine alone. Take of them what you will. Now on with the futile task:
Part 1: #89-56
89. CIMARRON (1931) dir. Wesley Ruggles
4th Academy Awards Best Picture Winner
The picture-perfect definition of a movie that has not aged well. It is a movie that tries to mythologize the virtues of Western expansion by telling a noble love story. The problem is that Western expansion is not a period that has fared well in recent assessments of history. In addition the movie is littered with a plethora of stereotypical depictions of African Americans, Native Americans, and Jews that are at best problematic and at worst downright offensive.
88. AROUND THE WORLD IN 80 DAYS (1956) dir. Michael Anderson
29th Academy Awards Best Picture Winner
This is a mess of a movie that begs you to be impressed by its outlandish smokes and mirrors so that you might hopefully overlook just how shallow it is. As a comedy it infrequently produces laughs and as a sprawling drama it is never serious enough to be compelling. As this is a story of two annoying white people who go around the world featuring a plethora of other white actors, rest assured that there’s plenty of brownface to shock your modern sensibilities. But worst of all, the movie is boring which is an unforgivable offence for a nearly three-hour movie.
87. GIGI (1958) dir. VincenteMinnelli
31st Academy Awards Best Picture Winner
An inferior rehash of the Broadway musical My Fair Lady (more on that later), the movie is a flighty musical in which our chief protagonist must be groomed in order to be a “proper” woman and one of the requirements of a “proper” woman must be that she falls in love with a man, even if that man is a serial womanizer and much, much older than one should be typically comfortable with. In other words, this has not aged well.
86. THE BROADWAY MELODY (1929) dir. HarryBeaumont
2nd Academy Awards Best Picture Winner
The early Academy Awards were an exercise in the organization trying to get a grip into what the awards were. As such, most of the early winners are forgettable misses. The Broadway Melody is notable for being the first major musical of the sound era but really that is about it as the film is absolutely ponderous by modern standards.
85. CRASH (2005) dir. PaulHaggis
78th Academy Awards Best Picture Winner
Crash is best described a much less elegant Love Actually. Here we get a story about race in America told with all the complexity of some white guy who just took an Intro to American Social Studies class in their freshman semester and is now righteously confident that they know everything about race in America and how to solve it (The Solution: Can’t We All Just Get Along? #alllivesmatter).
84. OUT OF AFRICA (1985) dir. Sydney Pollack
58th Academy Awards Best Picture Winner
This movie reads like a how-to manual for getting an Oscar. Step 1: Hire “serious” actors that the Academy knows and loves. Step 2: Set it in the past and in an exotic locale so that you get the production values of a “serious” movie. Step 3: Strip out any element of humour or action from the script in favour of meaningful glances and glacial pacing. Step 4: Set it during a momentous time in history so that by simple proximity to important historical events it can be deemed an “important” movie by default. Step 5: Collect your Oscar. Out of Africa successfully checks all these boxes. Unfortunately it doesn’t do one bit more.
83. CAVALCADE (1933) dir. Frank Lloyd
6th Academy Awards Best Picture Winner
Like Forrest Gump would do many years later, Cavalcade follows one family that is improbably present at most of the major events of the early 20th century from the Boer war to the death of Queen Victoria, from the sinking of the Titanic all the way past World War I into the then present of 1933. Unfortunately unlike Forrest Gump the movie doesn’t have an ounce of populist humour or a charming lead to make the trip entertaining.
82. DRIVING MISS DAISY (1989) dir. Bruce Beresford
62nd Academy Awards Best Picture Winner
On the one hand Driving Miss Daisy is a pleasant enough movie about the eventual friendship between a rich white woman and her black driver set during the middle of the 20th century. But on the other hand, it is a movie that is so blatantly unconcerned with making any statement of race and the power dynamics between the two during a time period when that was at the forefront of most of mid-century America that the movie just ends up being kind of offensive by default (especially in light of Spike Lee’s Do The Right Thing being completely shut out of the awards that year).
81. CHARIOTS OF FIRE (1981) dir. HughHudson
54th Academy Awards Best Picture Winner
This movie kicked off an era in the Academy Awards in which the Best Picture award was given to self-important middlebrow epics to the detriment of any movie that was remotely fun, creative, and original. When the most exciting and propulsive part of this movie about two sprinters is the slow-motion opening set to Vangelis’ iconic score, you know the movie is in trouble.
80. GOING MY WAY (1944) dir. Leo McCarey
17th Academy Awards Best Picture Winner
There is nothing necessarily bad about this musical about a priest from St. Louis arriving in New York and through song and dance charms his way into an initially reticent parish and ends up saving the parish as well. There is also nothing remarkable about it either with forgettable songs and a basic plot structure that has been imitated and bettered by other movies (See: “Sister Act 2: Back in the Habit”).
79. THE ENGLISH PATIENT (1996) dir. Anthony Minghella
69th Academy Awards Best Picture Winner
See “Out of Africa”. The only thing keeping this above that aforementioned movie is that at least the central romance between Ralph Fiennes and Kristin Scott Thomas is intriguing and exciting in a Casablanca-lite way. Unfortunately the rest of the movie is as eye-bleedingly boring as you’ve been led to believe.
78. THE GREAT ZIEGFELD (1936) dir. Ronald Z. Leonard
9th Academy Awards Best Picture Winner
If we could cut out all the actual talking and story in this movie and instead keep the spectacularly-staged and extravagant “Ziegfield Follies” song and dance routines that occupies most of the middle half of the movie (sans one unfortunate blackface minstrel routine) then this movie would rank much, much higher on the list. The fact that it sits this low tells you just how dull the rest of this nearly three hour movie is.
77. ALL THE KING’S MEN (1949) dir. Robert Rossen
22nd Academy Awards Best Picture Winner
While the movie is remarkable for being the first real movie to tackle the inherent danger of corruption that comes with being a politician, it also suffers because many other movies have come along since then to tackle that same material in much better ways starting with Eila Kazan’s A Face in the Crowd that came out less than a decade later.
76. GRAND HOTEL (1932) dir. Edmund Goulding
5th Academy Awards Best Picture Winner
The problem with Grand Hotel has little to do with the the quality of the stars involved or the source material and everything to do with the limitations of the early sound era. The staging of this film is extremely stilted due to how hard it was to capture dialogue cleanly and unfortunately can’t quite support the weight of the story. Still it is useful for trivia night as it is the only Best Picture winner not to receive any other Oscar nominations.
75. MY FAIR LADY (1964) dir. George Cukor
37th Academy Award Best Picture Winner
A movie (based on a play) whose base assumption is that a woman of lower class is not worth considering as a person unless that woman changes everything about who she was before in order to fit into bourgeoisie society. Despite Audrey Hepburn’s best efforts and a truly phenomenal soundtrack, the movie just cannot overcome the inherent nastiness and misogyny of its premise.
74. THE GREATEST SHOW ON EARTH (1952) dir. Cecil B. DeMille
25th Academy Awards Best Picture Winner
Often called the worst film to ever win best picture, this movie of life in the big-top circus is mostly just a bunch of soapy and breezy plot threads framed by long-sequences of circus antics. It is not wholly undeserving of its “worst film” tag because it is at least entertaining in the moment. But ultimately it is also entirely disposable.
73. AMERICAN BEAUTY (1999) dir. Sam Mendes
72nd Academy Awards Best Picture Winner
Given recent events regarding sexual misconduct in the entertainment industry, you can understand why a movie about a middle-aged suburban husband falling for and leerily pursuing a high-school student starring Kevin Spacey in the lead role is not a movie that has aged gracefully. But even besides that point, it is unclear exactly why we all fell in love with this movie in the first place.
72. YOU CAN’T TAKE IT WITH YOU (1938) dir. Frank Capra
11th Academy Awards Best Picture Winner
Usually I would be rejoicing the fact that a screwball comedy, a “low-genre” in the eyes of the Academy, would pick up the Best Picture Award. However the movie is (a) too long to be sustainably funny and (b) is a minor entry in a genre filled to the brim with all-time great movies. It can’t even make a claim as one of Frank Capra’s best movies (of which there are many candidates).
71. CHICAGO (2002) dir. Rob Marshall
75th Academy Awards Best Picture Winner
I will always be convinced that the only reason this decent-but-not-spectacular musical won best picture was to compensate for the fact that the Academy snubbed a truly groundbreaking and modern musical the year before in Moulin Rouge. True, there are some great numbers in this movie but it is surrounded by a story that is ultimately hollow, especially when compared to the minor musical masterpiece that was nominated the year before.
70. THE LIFE OF EMILE ZOLA (1937) dir. William Dieterle
10th Academy Awards Best Picture Winner
On the one hand, this movie manages to avoid one of the cardinal sins of a biopic by choosing not to make a sweeping tale about the entirety of the author’s life, instead focusing on a fascinating period in his life when he comes to the defence of Alfred Dreyfus, a Jewish captain in the French army who is wrongly accused of treason and espionage. On the other hand, this movie timidly shies away from any talk of anti-Semitism and even declines to actually call Dreyfus a Jew. And in does this in the context of an ascendent Nazi party in Germany on the eve of war, so ultimately this movie serves as a tragic reminder of how easily the rest of the world turned a blind eye to Nazism’s rise. Also it gets detracted points because at no point in this movie does Paul Muni look remotely close to the poster shown above.
69. GONE WITH THE WIND (1939) dir. Victor Fleming
12th Academy Awards Best Picture Winner
The only time I’ve watched the movie is before I ever moved to the United States and was thus completely unaware of the more intimate details of American racial dynamics. Even without that context, the movie just seemed like an overly long slog that was only famous by reputation. Of course now having lived in North America for more than a decade and seen all the developments that led to Charlottesville among others, the movie seems much more insidiously problematic with its portrayal of the glorious South. I do wonder if in twenty years we will talk about this movie the same way we talk about The Birth of a Nation, two iconic movies that represent important milestones in film but are too problematic to be admired.
68. DANCES WITH WOLVES (1990) dir. Kevin Costner
63rd Academy Awards Best Picture Winner
Speaking of ret-conning problematic periods of American history, here we have a white director deciding to tell a story about the Lakota Indians and their plight against the expansion of the United States and he has the gall to insert himself into that story of oppression by making him the hero who decides to side with the Indians instead of just trying to tell a story of Lakota Indian history from their own perspective. So yeah, it doesn’t look that great anymore.
67. OLIVER! (1968) dir. Carol Reed
41st Academy Awards Best Picture Winner
The problem with Oliver! is that it is at its heart a story about an orphan boy who lives during the middle of the industrial revolution and whose journey takes him past the less savoury and oppressed parts of this new society. In other words, it is a subject matter that should be much more tragic. But the movie is also a musical with peppy and uplifting numbers sprinkled throughout. While movies like West Side Story, All That Jazz, and Moulin Rouge prove that one can create musical that is steeped in tragedy, it is clear that Oliver! does not come anywhere close to finding that happy marriage to those two often disparate themes.
66. THE KING’S SPEECH (2010) dir. Tom Hooper
83rd Academy Awards Best Picture Winner
The King’s Speech is a clear example of the old guard of the Academy pushing for something traditional, safe, and middlebrow instead of remotely trying to reflect contemporary storytelling and trends. Had The Social Network – the movie that it beat out – won, it would have easily been a contender in the upper half of this list. But instead we are left with a stodgy if solidly acted costume drama about a king with a speech impediment (so as to let another actor claim the acting award for playing a disability) that has left absolutely no cultural impact on the world of film since it won.
65. MARTY (1955) dir. Delbert Mann
28th Academy Awards Best Picture Winner
Marty is not terribly ambitious filmmaking. This is not meant to be a knock against the film as it is a great little film about a butcher and happy bachelor (Ernest Borgnine) who keeps getting pressured by his family to meet some girl to fall in love with. And without planning it, that is exactly what he does in what has to be the first indie romantic comedy ever made. Unfortunately it is still too slight to rank too highly on this list.
64. THE BEST YEARS OF OUR LIVES (1946) dir. William Wyler
19th Academy Awards Best Picture Winner
It is remarkable that this movie, made in the rah-rah years of American exceptionalism following their victory in World War II, would be so honest about the less glamorous and hard side of the lives of veterans coming home from the war. Unfortunately a restrictive Hollywood-code and the cultural dangers of seeming un-patriotic (on the eve of McCarthyism) keep the movie from being a truly genuine portrait of the cost of war for veterans returning from war despite its best efforts.
63. BRAVEHEART (1995) dir. Mel Gibson
68th Academy Awards Best Picture Winner
One look at the poster to the left lets you know that any adherence to historical accuracy is going to be shunted for pure Hollywood bombast. The movie does have some spectacular battle scenes and its famous battle-cry speech is iconic for a reason but the movie reeks of self-importance and aggrandizing posturing while being completely unsubtle in its storytelling. It also continues a trend of Hollywood loving to reward their male actors who decide to go behind the camera, although in the case of Mr. Gibson that is a decision that has not aged well.
62. THE ARTIST (2011) dir. Michel Hazanavicius
84th Academy Awards Best Picture Winner
This small and charming film ran an Oscar campaign on the backs of Hollywood nostalgia and the novelty of possibly being the first silent film to win an Oscar since the original winner Wings. It is a pretty good throwback to an earlier era that borrows and calls back to every trope of silent movies, but in a paint-by-numbers way.
61. FORREST GUMP (1994) dir. Robert Zemeckis
67th Academy Awards Best Picture Winner
Take one white man with an unmentioned mental disability from which most of the movie’s humour is derived (to be played by a non-disabled person for a Best Actor Oscar) and throw him into most of the major activist events of the tumultuous sixties and seventies to the point that he inadvertently takes credit away from minority figures who were instrumental in those periods, and you see why this movie might land at around this spot on the list. Fortunately Mr. Hanks helps to make the journey tolerable.
60. MIDNIGHT COWBOY (1969) dir. John Schlesinger
42nd Academy Awards Best Picture Winner
The only X-Rated movie to win Best Picture (in an age when X-rated didn’t mean salacious soft porn) is a well acted and harrowing drama starring Dustin Hoffman and Jon Voight as two vagrants on the outskirts of New York in the 60’s falls into a category of movies that I wish I loved more, but ultimately is a movie I appreciate for what it represents rather than love for what it actually is onscreen.
59. HOW GREEN WAS MY VALLEY (1941) dir. John Ford
14th Academy Awards Best Picture Winner
Showcasing the Hollywoodification of Wales over and against any attempt at realism, this overly sentimental and overly serious movie spares very little humour as it chronicles the life of a Welsh mining family. Taken on its own terms, it is not a bad movie at all and in any other year would’ve won Best Picture and been forgotten. But this is the movie that beat out Citizen Kane for Best Picture, and unfortunately its reputation as an undeserving winner has dogged it ever since, as evidenced by my own inability to compare and contrast the two movies to find it wanting.
58. MUTINY ON THE BOUNTY (1935) dir. Frank Lloyd
8th Academy Awards Best Picture Winner
The movie is easily the best depiction of the famous mutiny and much of that is down to the fantastic performances of Charles Laughton as the tyrannical Captain Bligh and Clark Gable as the eventually mutinous Fletcher Christian. In between their central clash, we are treated to a swashbuckling adventure on the high seas that manages to skirt that line between being respectful to the source material and also being highly entertaining in its typically Golden-age-of-Hollywood lavish way.
57. KRAMER VS. KRAMER (1979) dir. Robert Benton
52nd Academy Awards Best Picture Winner
Kramer vs. Kramer is well-acted all round. It is sometimes painfully honest in its portrayal of a disintegrating family. However like many movies in this list, the intervening years between its exultant victory and now have revealed it to be slightly dated and quite frankly a little bit “men’s-rights” in the way in makes a villain (if at least a complex one) out of Meryl Streep’s character while laying very little blame at the feet of Dustin Hoffman.
56. GLADIATOR (2000) dir. Ridley Scott
73rd Academy Awards Best Picture Winner
There will always be a part of me that thinks this movie is a fist-pumpingly awesome movie about a superhero origin story disguised as a swords-and-sandals tale. Unfortunately that is all the tale of Marcus Aurelius (Russell Crowe) is, in which one-note gladiators battle one another and then join together to overthrow the supervillain Emperor (Joaquin Phoenix). It is a pure spectacle and arguably the biggest piece of pure action entertainment on this list but not the greatest movie to win Best Picture by a long-shot. Still, at least it tops this “Best of the Worst and Not-So-Great” Academy Award winners.