Ranking The Past 50 Best Picture Oscar Winners, From Magnificent To ‘What The Hell Were They Thinking?’

20. The Departed – 2006

Even though this was the movie that finally got Scorsese his Oscar, it’s not his best – it might not even be one of his five best – but it’s hard to deny this movie. Nicholson, DiCaprio, Damon, Marky Mark actually playing to his strengths for a change… I could go on and on. It might be slightly overrated – the rat on the windowsill? Come on. – but it’s still a really, really good movie and is, if nothing else, one of the best crime movies ever made.

19. In the Heat of the Night – 1967

I’m almost shocked that this was even made in 1967. And again, it’s hard to truly appreciate the movie disentangled of racial politics, but you’re not really supposed to. That’s sort of the point, and if a movie about a black cop asked to investigate a murder in a racist Southern town doesn’t seem relevant to you today, well… you and I are living in different worlds. Plus, are you really going to deny Sidney Poitier?

18. Ordinary People – 1980

A perfect family painfully falls apart, and whether intentionally or not, Robert Redford ended making a movie that helped define the almost tragic ennui that enveloped an entire nation in the waning days of the Carter years. This was the American Beauty of its time, and one of those most poignant depictions of the quiet horrors that so often lay underneath the comfortable, placid surface of suburbia.

17. Midnight Cowboy – 1969

You can make the argument that modern cinema began here. That is a wild overstatement, but this is the first movie to win an Oscar that really tapped into that auteur aesthetic that eventually dominated and transformed the landscape. It’s complex, morally ambiguous and doesn’t treat its audience like children. You could say that The Graduate really ignited this revolution two years earlier, and you’d be right, but Midnight Cowboy winning an Oscar might be what really opened the floodgates. You can thank a legendary performance by Dustin Hoffman, and it’s still the best thing that Jon Voigt has ever done aside from donating the sperm that eventually became Angelina Jolie. But that’s another story.

16. Patton – 1970

This is a polarizing movie, but that’s exactly what it needed to be because that’s who the man was. Patton, both the man and the movie, is a cultural flashpoint. He’s a dude who gloried in war and the movie doesn’t judge him for that. At least not overtly. There is something savagely American about the whole deal, and I’m not just talking about the whole Patton badass thing. It’s also tragic in a way, and Patton manages to explore all of it without being heavy-handed about it. That’s a hell of a trick to pull off.

15. Amadeus – 1984

This might be the most underrated movie on this list. I mean, who even talks about Amadeus anymore? But it’s a great movie, taking what could be a slow, boring story and giving it life by portraying Mozart as almost a young rock god. But rather than just another bio, it’s really a story about greatness and about how not quite being able to touch the magic can make a dude completely lose his shit. I feel you, Salieri. I feel you.

14. The Sting – 1973

It’s Paul Newman and Robert Redford running wild. What’s not to love? The scary thing is that this might not even be their best movie together, but it’s still awesome. Paul Newman was just the goddamn best.

13. Platoon – 1986

The ultimate “yo, war is fucking hell” movie, and the ultimate Oliver Stone movie. That is a hell of a combo. It’s not as crazy as Apocalypse Now, but that movie was almost too surreal to really cut to the core, you know? Platoon, on the other hand, tore open the Vietnam experience and forced people to stare at its guts. The result is one of the best war movies ever.

12. The French Connection – 1971

They should have just stopped trying to make cop dramas after this came out. That’s because they’ll never do it better. This is the OG, and it still kills today. It just has a gritty energy to it that pumps through the whole movie like a heartbeat. It never lets up, and nowhere is that more apparent than in Gene Hackman’s performance as Popeye Doyle. Oh, and it has one of the best chase scenes of all time. That always helps.

11. No Country for Old Men – 2007

A lot of people don’t like this movie, especially the ending, but the whole messy, unresolved nature of it all was sort of the point. Life – and especially crime – is dark, messy and often never really gets resolved in the way Hollywood lies to you about. There is a strong nihilistic streak running through this movie, personified perfectly by one of the great movie bad guys of all time, Javier Bardem’s Anton Chigurh. It’s ugly, it’s unsettling, and in the end, very, very powerful.