(List has been updated to include last year’s winner)

Here is the continuation of my futile task of ranking all the Oscar winners. At some point in this list (somewhere in the mid-30s) the movies move from being decent to legitimately great and worthy winners of the prize. Even if they beat out another nominee that I thought was better, it makes them no less worthy to at least be in consideration of the best film of their particular year. With that, let’s get on with the list:

Part 1: #90-57

Part 2: #56-26

Part 3: #25-1

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56. A BEAUTIFUL MIND (2001) dir. Ron Howard
74th Academy Awards Best Picture Winner

The true-story (or as “true story” as a Hollywood movie can get) of the Nobel-prize winning mathematician John Nash who was also a schizophrenic is about as conventional a feel-good biopic as you could make. There isn’t anything wrong with that and Ron Howard checks all the necessary boxes to create a competent portrait of a complicated and influential man. But one can’t shake the feeling that in the hands of a more ambitious director this tale could’ve been something more than merely competent.

55. TITANIC (1997) dir. James Cameron
70th Academy Awards Best Picture Winner

James Cameron’s epic about the famous sinking ship is certainly a spectacular achievement from a technical standpoint but just like his other technical wonder Avatar is a movie that fails at more basic things like creating a compelling plot with believable (and not incredibly cheesy) dialogue. This lack of a strong core to the movie is at least made better by the iconic film power couple of Leonardo DiCaprio and Kate Winslet (which gives it a bigger edge over Avatar) but away from the insane hype that followed its blockbuster success it is hard not to overlook its many flaws.

54. GENTLEMAN’S AGREEMENT (1947) dir. Elia Kazan
20th Academy Awards Best Picture Winner

Gentleman’s Agreement is part of the great tradition of movies that are notable for being the first real stab at depicting a social issue that looks extremely dated today. In this case, Gregory Peck plays a reporter who goes undercover as a Jew to expose the rampant antisemitism present in New York city. It was obviously progressive enough for it to get on the radar of the House Un-American Activities Committee and land a couple of writers on the Hollywood Blacklist. Yet it is also shockingly timid by today’s standards especially because it fails to make any mention of the Holocaust and its impact on the Jewish community which robs the movie of a lot of its bite.

53. THE DEER HUNTER (1978) dir. Michael Cimino
51st Academy Awards Best Picture Winner

The central metaphor for this film, the Russian roulette scene, may not have actually occurred historically but it certainly helps drive home the pointlessness that was America’s incursion and unending war in Vietnam. And as far as the movie is a depiction on the trauma that wrought upon American soldiers, it is a very good movie. However it falls into the trap of American exceptionalism by depicting its American soldiers as merely flawed and in-over-their-heads while the Vietnamese are savage and sadistic, when history bears out that there were very few innocents in that war and that the trauma that war inflicted upon America pales in comparison to what it did to the people of Vietnam.

52. ANNIE HALL (1977) dir. Woody Allen
50th Academy Awards Best Picture Winner

Had I made this list a few years ago there is no doubt that the Woody Allen comedy would have ended up higher on the list especially as I would’ve counted myself as a fan of his work. But unfortunately, the old excuses just aren’t cutting it anymore. And while part of me wants to judge a movie strictly based on merit, the problem with Allen’s work is that he inserts so much of himself into it that it becomes hard to separate the work from the creator. In this case, Annie Hall is a movie about a neurotic man who finds himself attracted to the original manic pixie dream girl until she becomes less of a fantasy and more of a woman with agency is simply another newly revealing chapter that perhaps we shouldn’t be as enamoured of the man and his work as we once was. Of course dropping the movie from near the top of the rankings to the bottom also seems impulsively revisionistic. So this spot feels about right.

51. SLUMDOG MILLIONAIRE (2008) dir. Danny Boyle
81st Academy Awards Best Picture Winner

The central problem with Slumdog Millionaire for me is its believability. Not the tragic backstory of Jamal Malik mind you, but the fact that improbably the order of the questions he is asked in his Millionaire game somehow lines up perfectly to create a linear retelling of that tragic backstory. It is also frequently a movie that frequently descends into poverty porn and is yet another story of India told by a white man that reduces a diverse and immense society to its worst possible corners. However it is also pretty entertaining.

50. SHAKESPEARE IN LOVE (1998) dir. John Madden
71st Academy Awards Best Picture Winner

This movie owes its victory thanks to the nasty, brutish, and bullying Oscar campaign put out by Harvey Weinstein,  a man whose stock has deservedly plummeted recently. And it is unfortunate that this movie is mostly remembered as the movie that bullied its way to the Oscar at the expense of the superior Saving Private Ryan because taken on its own terms, the movie is a witty and frequently funny romantic comedy with two great leads that is ultimately satisfying in its own right. But it also didn’t deserve to win Best Picture.

49. A MAN FOR ALL SEASONS (1966) dir. Fred Zinnemann
39th Academy Awards Best Picture Winner

The movie, based on Robert Bolt’s play about Sir Thomas More’s refusal to acknowledge Henry VIII’s divorce and remarriage, suffers  from being a little bit too stagey as almost all the scenes are either filled to the brim with conversation (and obviously adapted from the play) or are quietly contemplative (obviously added from the play) with little in between. But with Paul Scofield anchoring the proceedings as Sir Thomas More and being surrounded by Robert Shaw and Orson Welles among others, the film never truly veers into dull territory and remains compelling throughout.

48. BEN-HUR (1959) dir. William Wyler
32nd Academy Awards Best Picture Winner

Admittedly the movie is a frequently entertaining movie with a vast and epic sweep but it is brought down by being just way too long of a movie and preachy to boot. Charlton Heston’s performance choices are also slightly odd to the point of distraction. But what everyone who has seen this movie remembers about it is the expansive and action-packed chariot race in the middle of the film that is every bit as iconic as advertised, accomplished using practical effects and still more exciting and thrilling than any CGI-fest today (including the ill-conceived remake that one should avoid at all costs).

47. GANDHI (1982) dir. Richard Attenborough
55th Academy Awards Best Picture Winner

Of the big sprawling epics of the 1980s that went on to win Best Picture, Gandhi is at least realistic in its expectations as the movie begins by telling us that “No man’s life can be encompassed in one telling.” In spite of that axiom, this is still an overly stuffed movie that covers a lot of terrain beginning with Gandhi’s activism in South Africa and his eventual work in liberating India from its colonial powers all the way to his death. With this much stuff packed in, the three-hour movie can do no more than cover the basics of the events and hope that Ben Kingsley can add something in between to give us a glimpse of Gandhi himself. Fortunately Kingsley is up to the task.

46. WINGS (1927) dir. William A. Wellman
1st Academy Awards Best Picture Winner

The inaugural winner of the Best Picture award is a great example of the kind of melodramatic storytelling emblematic of the silent era. Though it is two and a half hours long, the movie breezes by at a pace that belies many of the talkie winners on this list. However the most remarkable part of the movie is the aerial battle scenes that are still impressive by today’s standards, making it a minor miracle that it was filmed almost a century ago.

 

 45. MILLION DOLLAR BABY (2004) dir. Clint Eastwood
77th Academy Awards Best Picture Winner

The first two-thirds of this boxing movie is a great gender-reversal Rocky clone featuring a much more talented cast and better direction from Clint Eastwood. It is a solid underdog sports story that progresses along nicely providing all the thrills that you would expect in a boxing movie. Then comes the left-turn maudlin ending where the movie suddenly changes from sports drama into full-on weepie with all the emotional manipulation that comes with it.

44. BIRDMAN (2014) dir. Alejandro Gonzalez Inarritu
87th Academy Awards Best Picture Winner

So apparently this movie inspires very disparate emotions. There are those who consider this to be the absolute worst movie to ever win Best Picture (I will warrant that they have not in fact seen all of those winners yet) and then there are some (a much smaller number) who think that it’s a minor masterpiece. I am personally the seemingly rare person who just has little to no response to it at all. It’s an entertaining enough movie with an interesting central conceit of appearing to happen in one take (even if it’s not). It also gave us the reemergence of Michael Keaton which I’m grateful for, but apart from this there is absolutely nothing else noteworthy about the movie, good or ill. So right smack in the middle of this list feels about right.

43. MRS. MINIVER (1942) dir. William Wyler
15th Academy Awards Best Picture Winner

The movie is an unabashed piece of propaganda that was instrumental in buoying the British during World War II as well as making America a little bit more amenable to jumping into the fray. But it is also a well-acted drama anchored by Greer Garson as a British homemaker who finds herself and her village thrust into the heart of war. It is not subtle in the least, but it is also expertly crafted from beginning to end.

 

42. THE LAST EMPEROR (1987) dir. Bernardo Bertolucci
60th Academy Awards Best Picture Winner

It is an extremely long and drawn out movie about, as the title might suggest, the life of the last emperor of China. The use of English instead of making everyone speak Mandarin and force us to read subtitles is an endless distraction. And yet Bernardo Bertolucci’s film is nothing short of a spectacle that overcomes most of its flaws. The scenes set in the Forbidden City are breathtaking and its travails during a tumultuous century in the centuries old Chinese empire are epic in its sweep. Unfortunately the most dull part of the entire movie is the life of the last emperor himself.

41. RAIN MAN (1988) dir. Barry Levinson
61st Academy Awards Best Picture Winner

What everyone remembers about this movie is the tic-filled performance of Dustin Hoffman as an autistic savant which is where all the critical acclaim and awards went to (Hoffman won Best Actor for this role). What everyone should remember about this movie is the equally impressive and much subtler performance of Tom Cruise as his hustler brother. This performance proves that at his peak Cruise was untouchable as an artist, the rare actor with impeccably good looks but more impressive acting chops. And with every re-visit I make of his early roles, I can only hope that at some point he will take a break from his “Mission Impossibles” and whatever other franchise he’s trying to start and return to his dramatic roots.

40. TOM JONES (1963) dir. Tony Richardson
36th Academy Awards Best Picture Winner

It is a minor miracle that this farcical and light-hearted comedy, featuring what would be the 18th century version of juvenile humour was even nominated let alone took home the golden statue. It is rude, anachronistic, and blisteringly paced. In other words, the complete opposite of the kind of movie that should win the Oscar. And while it is also kind of vacuous, a little misantrophic, and extremely silly, it is also a irreverent and audacious addition to the stodgy Academy’s ranks. Among the presence of the rest of these prestigious movies, it sticks out like that nephew who decides to wear a tuxedo t-shirt to a wedding. And at some level, that’s just a little bit awesome.

39. ARGO (2012) dir. Ben Affleck
85th Academy Awards Best Picture Winner

The biggest mistake director Ben Affleck made in Argo is placing actor Ben Affleck in the leading role of this movie as the CIA agent tasked with sneaking six American embassy workers out of Iran. Fortunately director Ben Affleck also surrounded the rest of the movie with a cavalcade of great actors and actresses who make this tense and thrilling drama a great spy procedural to rival the best of the genre. There is a little bit of Hollywood patting itself on the back with this movie (Hollywood producers can be American heroes too!) but we’ll allow it because this assured picture by director Ben Affleck who is quickly establishing himself as being much better than actor Ben Affleck.

38. THE LOST WEEKEND (1945) dir. Billy Wilder
18th Academy Awards Best Picture Winner

As the first film to tackle head-on the issue of alcoholism, it has been easily dismissed in recent years as an after-school special on the subject. However to do so would be to ignore two things: First, the magnetic performance of Ray Milland is a captivating and frightening portrait of a man consumed by his addiction. While it is naive to assume that this is the experience of every addict, it is also undeniable that at a basic level Milland manages to externalize the inner workings of some addicts. But more importantly this movie succeeds because of Billy Wilder who brings his cynical worldview – usually in the backdrop of his movies – to the forefront with great effect as he creates a psychological film noir that is compellingly tragic.

37. FROM HERE TO ETERNITY (1953) dir. Fred Zinnemann
26th Academy Awards Best Picture Winner

This movie is everything Michael Bay wished Pearl Harbor was going to be and failed miserably trying to achieve that (sure, on the surface that seemed like an unnecessary dig at Michael Bay but can you really make an unnecessary dig at Michael Bay?). The film is best known for its famous beach romance scene, but it is also so much more than that as it follows the lives of three soldiers in the months leading up to Pearl Harbor. And when those three soldiers are played by Burt Lancaster, Montgomery Clift, and Frank Sinatra you know the end results are going to at the very least be entertaining.

36. THE SOUND OF MUSIC (1965) dir. Robert Wise
38th Academy Awards Best Picture Winner

The first half of the movie is a flighty and breezy romp through the German countryside filled with catchy songs and scenes that have been burned into my memory. Julie Andrews and Christopher Plummer are iconic as the governess Maria and the Captain Von Trapp. Up until the intermission it is a perfect little piece of entertainment. But then in the second-half we get the most unexpected emergence of Nazis in the movies that undoubtedly helped push the movie to Best Picture by making it seem more “important” but is also much weaker in comparison to the near-perfection that it the opening half of the movie.

35. ROCKY (1976) dir. John G. Avildsen
49th Academy Awards Best Picture Winner

Although the sequels of ever decreasing quality might suggest otherwise (sans Creed!), the fact is that Rocky is not only a good movie, but a great sports movie. There is something so classically pleasing about the story about the working class southpaw with little-to-no chance at the title going up against the great Apollo Creed for his shot at greatness. But what makes this movie great is that it plays this story straight without any descent into camp. There is no “Eye of the Tiger”, no Mr. T, no Ivan Drago. Instead there is just the purity of an underdog tale told extremely well that finds meaning beyond the narrow terms of victory on the mat.

34. THE HURT LOCKER (2008) dir. Kathryn Bigelow
82nd Academy Awards Best Picture Winner

It is still the best movie made about the currently ongoing Iraq War, and this is probably because the movie refuses to either preach to the choir nor hurls daggers at the conflict either. This is not to say the movie has nothing to say about the war and the people who fight it, but rather that the issue is immensely complicated. Focusing on Jeremy Renner’s reckless and extremely proficient bomb-defusion specialist, it is frequently thrilling in a matter-of-fact way showing the risks that come part in parcel with the profession. But it is in the quiet moments where Renner’s character has no overriding drive and as a result, no overriding purpose that the movie elevates itself from being a mere war movie.

33. THE SHAPE OF WATER (2018) dir. Guillermo Del Toro
90th Academy Awards Best Picture Winner

This romantic horror fantasy about a fish-man falling in love with a woman is easily the weirdest movie to ever win the Best Picture Oscar, and there is something wonderful about knowing that a movie with a vision this eccentric is “Oscar-worthy”. But beneath its veneer is in fact a very traditional movie made explicitly by Del Toro in order to evoke classic Hollywood with such love and dedication to craft that it almost makes you forget the movie’s specific and unique oddness.

32. AN AMERICAN IN PARIS (1951) dir. Vincente Minneli
24th Academy Awards Best Picture Winner

Like most musicals of this era the major setpiece of this movie which in this case is the fifteen minutes or so unbroken sequence of dance set to Gershwin’s “An American in Paris” is spectacular. It is a masterpiece of choreography and design and is all framed by the inimitable Gene Kelly who remains the most charismatically magnetic dancer to grace the big screen. The movie stumbles however when it has to actually try to do anything remotely close to telling a story, but it is the musical numbers that are the calling card of this movie and they are each in their own way iconic all the way up to its euphoric concluding piece.

31. AMADEUS (1984) dir. Milos Forman
57th Academy Awards Best Picture Winner

Unlike most of the overwrought and overproduced prestige epics that the Academy fell head-over-heels over in the 80s, Amadeus succeeds by being suitably eccentric, much like the movie’s namesake. Tom Hulce as the manchild Mozart is entertaining from beginning to end but it is his rivalry with the much more serious Salieri (F. Murray Abraham) that ups the drama to a different level. It is also a refreshing take on a story about creativity, brazenly arguing that sometimes it doesn’t matter how hard you work because you’re just going to beaten by someone who can create better works than you without even trying. Sometimes life truly isn’t fair.

30. WEST SIDE STORY (1961) dir. Robert Wise
34th Academy Awards Best Picture Winner

While this is not the best musical of all time (it needs to get in line behind Singin’ in the Rain, Cabaret, All That Jazz, The Wizard of Oz, The Umbrellas of Cherbourg, and A Hard Day’s Life at the very least) it is in fact very, very good. The music boasts the legendary power-duo of Leonard Bernstein and Stephen Sondheim, the choreography is some of the best ever committed to celluloid, and the production manages to turn the Upper West Side into a fantastical enchanted place splashed with spectacular technicolor. So who cares if the movie is almost note-for-note “Romeo and Juliet” but set in modern day New York – the cliche move of every high school drama group?

29. THE BRIDGE ON THE RIVER KWAI (1957) dir. David Lean
30th Academy Awards Best Picture Winner

As one might have surmised by now, there are a LOT of war movies that ended up as Best Picture winners. What sets The Bridge on the River Kwai apart from most of those movies however is that it is less a movie about the heroism of war as it is about the complete loss of perspective as both captors and captives of a Japanese POW perversely are joined together by the task of building a bridge. Away from the combat fields where those heroes of war are made the crew settle into a pattern of normalcy by clinging to a military discipline and their singular obsession with the task at hand naturally will face a breaking point, all of which makes it an intense exploration of duty in the face of impending madness.

28. IT HAPPENED ONE NIGHT (1934) dir. Frank Capra
7th Academy Awards Best Picture Winner

The set-up is as screwball as they come: an heiress runs away from her family and bumps into an out-of-work newspaper man as she tries to unite with her fiancee to elope, and the newspaper man agrees to help the fish-out-of-water in exchange for an exclusive. Of course as with all screwball comedies, that is merely just the set-up for hijinks, witty repartee, and a great romantic movie. It is also the first  movie (of three) to win the “Big Five” (Picture, Director, Actor, Actress, Screenplay) and deservedly so.

 

27. PLATOON (1986) dir. Oliver Stone
59th Academy Awards Best Picture Winner

Unlike The Deer Hunter with its decidedly one-sided depiction of the Vietnam War, Platoon succeeds by taking a much more amoral approach. It probably helped that the movie was directed by Oliver Stone, an actual combatant during Vietnam, as the chaos and brutality of the combat feels shockingly visceral and coming from the experiences of someone who had a ground-level view of the experience. And more tellingly, the movie advances the (correct) idea that the colour of one’s uniform does not make you immune from the immorality of war.

26. HAMLET (1948) dir. Laurence Olivier
21st Academy Awards Best Picture Winner

Laurence Olivier’s Hamlet is undeniably not as great as it could have been. It is the rare Oscar winner that I wish was longer but this is the case because Olivier got rid of almost all of the political elements in Shakespeare’s play in order to keep it under three hours. But what remains is still essentially Shakespeare, which instantly makes it one of the best screenplay. And the success of this movie is proof positive that Shakespeare, though best on stage, is perfectly acceptable on screen as well. Of course, The Red Shoes should have obviously won.

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Part 1: 90-57

Part 3: 25-1

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