(List has been updated to include last year’s winner)
And we have finally arrived at the Top 25 Oscar winners and suffice to say, these are all just great films with very little separating them. To be honest I could move any of these movies up and down a couple of slots and not have to work too hard to convince myself that that’s their correct spot. But after spending so much of my time bitching and moaning about how the Oscars get it wrong, here is the indisputable evidence that sometimes they get it right:
Part 3: #25-1
25. THE STING (1973) dir. George Roy Hill
46th Academy Awards Best Picture Winner
There is a strong argument to be made that this movie amounts to nothing more that Paul Newman and Robert Redford shooting the breeze for two hours and they wouldn’t necessarily be wrong about that. Every time I’ve watched this movie I’ve struggled to explain its labyrinthine plot let alone how the central con of this movie plays out. But the movie is such a slick and effortless piece of fun that I don’t even notice. There is something infectiously joyous in seeing Redford and Newman smirk and wink their way into conning their victim out of a huge chunk of change and if it doesn’t accomplish more that it hardly ever matters.
24. TERMS OF ENDEARMENT (1983) dir. James L. Brooks
56th Academy Awards Best Picture Winner
If you haven’t noticed by now, the Best Picture winners are inordinately dominated by male-skewing stories with nary a fully formed female character in sight. This is part of what makes Terms of Endearment so special as it is a “woman’s picture” with two fully formed and complicated female characters played magnificently by Debra Winger and Shirley MacLaine. Buoyed by a magnificent script by James L. Brooks, who deftly switches between comedy and drama, it is a fitting showcase not just of the two actresses (and Jack Nicholson) but a wonderful portrait of the complicated relationship that forms between a mother and her daughter. And it earns every tear it wrings out of you.
23. THE FRENCH CONNECTION (1971) dir. William Friedkin
44th Academy Awards Best Picture Winner
The French Connection is quite simply a well-acted and well-directed cop thriller. It is exactly the kind of movie that usually gets completely ignored by the Academy and yet miraculously the movie won. Most of this has to do with the grit and determination that Gene Hackman plays cop Popeye Doyle and William Friedkin’s direction who basically provided the template here for cop thrillers for decades to come. It also features one of the best car chases of all time. Everything about this movie simply punctuates that this is not your typical Oscar winner, but thank goodness it is.
22. IN THE HEAT OF THE NIGHT (1967) dir. Norman Jewison
40th Academy Awards Best Picture Winner
In the Heat of the Night was one among a slew of game-changing nominees that ultimately and fundamentally changed how Hollywood operated by ushering out the studio system and bringing in the American New Wave. And while the Academy’s choice might seem a little safe compared to its fellow nominees The Graduate and Bonnie and Clyde, this does not diminish the movie’s own greatness. It stars Sidney Poitier as a decorated black detective who is initially arrested as a suspect for a murder in the recently desegregated Mississippi and eventually leads the investigation in spite of the deep prejudices of its residents. Poitier kicks ass, which is exactly as empowering as that sounds.
21. PATTON (1970) dir. Franklin J. Schaffner
43rd Academy Awards Best Picture Winner
In the history of Hollywood making biopics of luminary historical figures there has never been, and probably will never be, a more perfect pairing than George C. Scott playing General Patton. Scott is Patton. The movie, written in part by Francis Ford Coppola (more on him later) plays out like a Shakespearean epic as it paints a compellingly complicated portrait of a man who seemed to have been transplanted out of the middle ages who finds himself at home in war and displaced in times of peace. While one could read the film as simply a pro-war film made during the height of the Vietnam War, that denies the ambiguous and complicated picture that Franklin J. Schaffner paints of America’s would-be warrior-king.
20. THE SILENCE OF THE LAMBS (1991) dir. Jonathan Demme
64th Academy Awards Best Picture Winner
Horror is a genre that is frequently looked down upon by the stodgy Academy so it is a testament to how good The Silence of the Lambs is that it managed not only to win Best Picture but all the “Big Five” awards (Picture, Director, Actor, Actress, Screenplay), being the last movie to do so. Anchored by two powerhouse performances in Jodie Foster as FBI agent Clarice Sterling and Anthony Hopkins as the terrifyingly alluring Hannibal Lecter, it is a movie that doesn’t so much try to scare you (although it does do that) but instead unsettlingly burrows under your skin. It is not the most challenging film on this list, but it is evidence of how to do a mainstream thriller right.
19. THE DEPARTED (2006) dir. Martin Scorsese
79th Academy Awards Best Picture Winner
On the one hand it is quite obvious that The Departed won not solely on the backs of its own merit but as a severe course correction for all the many ways the Academy had snubbed Martin Scorsese and his work (with Taxi Driver, Raging Bull, and Goodfellas not winning being the greatest of those snubs). But to simply attribute this win to being a de-facto lifetime achievement award is to forget that The Departed is a frequently engrossing and well-acted gangster thriller in its own right. While it is also notably Jack Nicholson’s last film role before he retired to his Laker’s courtside seat, the movie is a much greater showcase of the “kids” in this movie with Leonardo DiCaprio pulling in a typically workmanlike performance, Mark Wahlberg emerging as a serious actor, and Matt Damon as arguably the best of the three as a double agent cop.
18. ON THE WATERFRONT (1954) dir. Elia Kazan
27th Academy Awards Best Picture Winner
This is the definitive performance of Marlon Brando’s early career as he plays a dockworker who singlehandedly tries to rally his fellow dockworkers against a corrupt and murderous union boss. Unlike most films of the era, On the Waterfront was shot on location in Hoboken, New Jersey, giving the movie a feel of docu-drama immersive realism that only heightens the drama and makes the allegorical religious imagery seem not so blatantly obvious. It has all the rage and sadness of its contemporary Rebel Without a Cause, but in the hands of Brando and crew becomes a compelling portrait of a man trying to do the right thing in spite of his disenfranchised frustration.
17. REBECCA (1940) dir. Alfred Hitchcock
13th Academy Awards Best Picture Winner
While Rebecca is no doubt a worthy winner of the Best Picture award, it is a blight on the Academy that this is the only movie they found room to honour in Alfred Hitchcock’s illustrious filmography. Laurence Olivier and Joan Fontaine are fantastic in this twisty gothic-noir of a tale in which the spectre of Olivier’s first wife haunts his current relationship to his new wife (Fontaine) as it is framed by the magnificently ornate Manderley. Unfortunately the Production Code managed to get its grubby hands all over the movie, blunting the ending somewhat. But that doesn’t diminish the fact that it is one of Hitchcock’s best, and a wonderful placeholder in the Academy of the power of his work.
16. SPOTLIGHT (2015) dir. Tom McCarthy
88th Academy Awards Best Picture Winner
There is something so effortless about this newspaper procedural about the Boston Globe’s investigation into child sexual abuse in the Catholic Church that it can fool you into thinking there is very little craft involved. But that would be a mistake. This is an understated and extremely precise movie that somehow managed to take a complex case and a complex investigation and distill it into a clear and presentable form that is extremely easy to follow. It manages to walk the fine line between shining a light on the horrific systemic way that the church hid and protected alleged sexual abusers without being exploitative towards the victims. And its standout cast is perfectly up to the task of delivering the gravity that this story demands without ever veering into the melodramatic. It is a movie that compelling lays out its case to you while respecting your intelligence. And by doing so, it becomes the best journalistic movie since All the President’s Men which puts it in very haughty company.
15. ORDINARY PEOPLE (1980) dir. Robert Redford
53rd Academy Awards Best Picture Winner
Suicide, grief, and depression is often something that is handled poorly in movies, easily veering into the emotional manipulative territory. This is gladly not the case with Ordinary People as it provides a stark glimpse into a family falling apart after the death of the eldest son. It treats depression in a matter-of-fact way and treats the hurt parties of this tragedy with equal empathy. By refusing to embellish the tragedy with melodramatic flourishes, Robert Redford forces us to confront grief, trauma, and depression in a way most of society wishes we would ignore and is all the more powerful for that.
14. ALL QUIET ON THE WESTERN FRONT (1930) dir. Lewis Milestone
3rd Academy Awards Best Picture Winner
Most war movies, despite their underlying message, end up in some way glorifying the conflict. The grand exception to this is Lewis Milestone’s spectacular and brutal adaptation of Erich Maria Remarque’s novel which immerses you in the muck and grime of the trenches of World War I, depicting as close a picture of hell as has ever been put to celluloid. Featuring a harrowing soundscape that belies its reputation as an early talkie, it banishes any romanticizing of the war and instead reveals it for the brutish and pointless affair that it was as one-by-one school boys get mowed down and with them the hopes of the future they could’ve built.
13. THE LORD OF THE RINGS: RETURN OF THE KING (2003) dir. Peter Jackson
76th Academy Awards Best Picture Winner
There is no doubt that when this movie went on to sweep every award in the categories that it was nominated that the Academy was rewarding the trilogy as a whole and not just this final instalment. And while personally I believe that Fellowship of the Ring is the better movie in this trilogy, there is no doubt that as a capper to the phenomenal trilogy Return of the King is a remarkable achievement in its own right as it juggles the seemingly endless plot points and through lines established by the previous two movies to reach a ending that is narratively satisfying in a way few other trilogies have managed to garner (granted, it did this by having about seven endings to the movie, but we’ll forgive it that).
12. LAWRENCE OF ARABIA (1962) dir. David Lean
35th Academy Awards Best Picture Winner
No film probably takes greater advantage of the medium on this list better than Lawrence of Arabia. From beginning to end the movie is a spectacle, filling every inch of the screen with such great detail that small televisions will miss a plethora of detail. It is a gargantuan epic at close to four hours long and yet it is also an intimate portrait of a complicated man who rallied together disparate tribes to do battle against the Turks. But what lingers in this movie has nothing to do with the plot, but rather it is the desert vistas, the haunting look of Peter O’Toole, and the feeling of grandness that David Lean imparts upon the viewer.
11. SCHINDLER’S LIST (1993) dir. Steven Spielberg
66th Academy Awards Best Picture Winner
Much like his friend Scorsese, Steven Spielberg is another director whose best work (Jaws, Close Encounters of the Third Kind, Raiders of the Lost Ark, E.T.) was dismissed by the Academy by being juvenile and not being prestigious enough. One might be tempted to see Schindler’s List then as Spielberg’s ploy to release a prestige picture to finally nab him that statuette. But to assume that would be to deny the film’s greatness on its own right. Schindler’s List is easily the best movie ever to be made about the Holocaust, a somehow hopeful film in the midst of unthinkable cruelty that not only forces us to stare at the depths of depravity in Ralph Fiennes and the death camp he runs but also to see that even in the midst of seeming total evil bravery and decency still can be present in Liam Neeson’s Schindler. And more than just a cynical play for an award, Schindler’s List is oozing with Spielberg’s undeniable sincere passion to portray this human tragedy correctly and that passion is infectious.
10. 12 YEARS A SLAVE (2013) dir. Steve McQueen
86th Academy Awards Best Picture Winner
People avoid this movie because they assume it delves into some sort of grief porn. That would be a terrible mistake to make because the power of Steve McQueen’s portrait of slavery is that it presents this admittedly harrowing material in a matter-of-fact way, refusing to make it exploitative or to temper it down for a middle-brown audience. The most shocking thing about this movie is that it shines a light on just how ordinary evil is. None of the slave-owners are such over-the-top villains as to allow us to disassociate from them. Instead McQueen shows slavery for what it was: Not as an institution created by inhuman monsters, but as an evil perpetuated by ordinary people and rooted in everyday life. And that is frankly much more terrifying than grief porn.
9. MOONLIGHT (2016) dir. Barry Jenkins
89th Academy Awards Best Picture Winner
Lost amidst the chaos of how it was announced as the winner, is the pure shock of just how right the Academy got it when they went with this quiet and meditative art film over the Hollywood love letter in La La Land. This movie is so lyrically beautiful, focusing on the life on Chiron, a poor, gay, and black person in Miami as he navigates the perilous task of growing up. The power of the movie lies in its insistence not to turn it into a message film about what it means to be poor, gay, and black in America. Instead Barry Jenkins paints a stunning hyper-personal portrait of Chiron, done with warmth, grace, authenticity, and such specificity that it conversely becomes a transcendent tale of the universality of human experience.
8. UNFORGIVEN (1992) dir. Clint Eastwood
65th Academy Awards Best Picture Winner
In the very definition of biting the hand that feeds him, Clint Eastwood deconstructs the Western myth so thoroughly that every Western after has had to contend with its ramifications. Eastwood plays the Schoefield Kid, a retired gunslinger who is called back into action when a corrupt sheriff starts terrorizing the citizens of his town. But unlike in Western’s past, including one’s starring Eastwood, this time around he sees himself as no hero and takes no pleasure as he descends upon the town like an angel of death meting out vengeance but finding very little justice in a film in which the cost of violence is given its terrifying and debilitating weight.
7. ONE FLEW OVER THE CUCKOO’S NEST (1975) dir. Milos Forman
48th Academy Awards Best Picture Winner
In many ways Jack Nicholson’s career is synonymous with the Academy as the most nominated male actor and one of its biggest winner. He was never better than in this movie made during his peak in the 70s about a normal man who finds himself in a mental institution in order to escape hard time. It quickly evolves into a riotous raging against the machine as through his charisma and charm builds a makeshift family from the inmates and raises hell against its tyrannical warden. Its ending remains one of the biggest gut punches in film history, punctuated by the sheer joy on display before that point.
6. CASABLANCA (1942) dir. Michael Curtiz
16th Academy Awards Best Picture Winner
The movie is eminently quotable, the cast of characters and the actors who play them are legendary from Humphrey Bogart to Ingrid Bergman to Claude Rains and Peter Lorre, and the setting is one so lush as to be befitting of classic Hollywood. The fact that it was made during the height of the studio system in Hollywood and was meant to be released quickly and forgotten just as easily speaks to the lighting-in-a-bottle magic that this film is. Part adventure film, part romance, part thriller, frequently funny, sometimes heartbreaking, and exciting from beginning to end, the film is just about perfect.
5. THE GODFATHER: PART II (1974) dir. Francis Ford Coppola
47th Academy Awards Best Picture Winner
The world is basically divided into two kinds of people: Those who think the original Godfather is the better film and those who think Part II is superior (those who think Part III deserves to be included in this conversation are not worth knowing and will be politely ushered out the door). Clearly, I fall in the former camp but it is truly splitting hairs for me. This sequel/prequel to the original deepens the mythology of the Corleone clan by focusing on Vito’s backstory but it also runs over the same ground with Michael’s arc as the journey from Don to very evil Don is not nearly as dramatic as the arc he undergoes in the original movie. Still don’t let that fool you into thinking that this movie is an inferior movie, because it is still very, very good. Also it is the second Robert De Niro movie to ever win Best Picture which is absolutely INSANE (See: Martin Scorsese’s repeated snubs by the Academy).
4. NO COUNTRY FOR OLD MEN (2007) dir. Joel and Ethan Coen
80th Academy Awards Best Picture Winner
Where the Godfather movies are an inversion of the American dream, No Country for Old Men is a completely nihilistic dismantling of it altogether. The best adaptation of a Cormac McCarthy novel owes much of its success to the Coen brothers whose lean and mean script lays bare the realities of one generation’s values and goals giving way to the next and the callous disregard this new world has for the old ways. The three leads put in career-best performances with Javier Bardem’s serial killer rightfully getting most of the attention. While There Will Be Blood arguably should have won this year, there is no shame in losing out to this masterpiece in its own right and a cornerstone to the argument that 2007 was one of the best years ever in film.
3. THE APARTMENT (1960) dir. Billy Wilder
33rd Academy Awards Best Picture Winner
Billy Wilder has always had a little bit of a cynical edge to him even in his most comedic moments but what sets The Apartment apart from the rest of his work is that he seems to have struck the perfect balance of embodying his generally cynical worldview while still leaving room for a little bit of hope. And he couldn’t have picked two better people to embody that mix than in everyman Jack Lemmon who perfectly portrays the optimistic company man who slowly but surely has his cheeriness worn down and Shirley MacLaine as the outwardly happy elevator operator who is shielding her broken heart. It is this mix of farcical and witty comedy with an undertow of heartbreak and sadness that makes this movie great. Also “Shut up and deal” is perhaps the best last line of a movie ever.
2. ALL ABOUT EVE (1950) dir. Joseph L. Mankiewicz
23rd Academy Awards Best Picture Winner
All About Eve is a deliciously catty backstage story of Margo Channing (Bette Davis) stage veteran and the ingenue Eve Harrington (Anne Baxter) who becomes enamoured with her and eventually tries to usurp her. But there is so much more going on than just backstage politics as the film is an incisive commentary on the double standard of the superficialities women have to endure in their quest to success. That the movie also inadvertently has Marilyn Monroe show up in a cameo and threaten to steal all the main cast’s thunder is just another sign of the pleasures available in this behind-the-scenes drama. Also this movie has George Sanders and everything is better with George Sanders.
1. THE GODFATHER (1972) dir. Francis Ford Coppola
45th Academy Awards Best Picture Winner
I realize this is not an entirely inspired or original choice for the top, but that’s because sometimes the obvious choice is obvious for a reason. The Godfather, so frequently parodied and referenced, is surprisingly a movie that maintains its power every time I watch it. Unlike Part II which wonderfully fills the backstory of the Corleone clan, the original is singularly focused in the rise of Michael Corleone (Al Pacino) from reluctant son who wants nothing to do with the family business to becoming the Don Corleone and is all the better for it. It is the quintessential inversion of the American dream, and the rare movie where the insane hype and praise that has been heaped upon it all these years (and repeated Thanksgiving showings on AMC) has done little to dull its power.
(Correction: In an earlier post I said The Godfather Part II was the only Robert De Niro film to win a Best Picture Oscar. I obviously forgot Michael Cimino’s The Deer Hunter where De Niro is on the freaking poster, so that is obviously an egregious mistake on my part. It has been corrected and now I will retreat in my shame.)