What’s the greatest movie to win a Best Picture Oscar from the last 50 years? That’s the question we’re here to answer today. We’re going to take the last 50 Oscar winners and rank them, and during this journey, you might be surprised to find that some of these movies aren’t nearly as good as you might expect while others simply aren’t very good at all. Time has not been kind in a few cases. But it’s okay, we’ll get through this together, and when we’re done, we’ll crown the best Oscar winning movie of the last half century. Let’s just get to it.
50. Out of Africa – 1985
It’s long, slow, boring and completely full of itself. Basically, this is the sort of movie that everyone makes fun of when they talk about clichéd Oscar borefests. It pretty much won because it was supposed to win, largely because everyone just assumed it would be good thanks to leads Meryl Streep and Robert Redford. Call me crazy, but an Oscar winner should probably win for a better reason than “Hey, those guys are in it.”
49. Crash – 2005
Hollywood takes on race relations, and naturally, it does so in the most obvious, hammy way possible. To hell with the Oscars, this movie should have won a Razzie.
48. Oliver! – 1968
It has an exclamation point, so it must be good! Not so fast, my friend. The biggest problem is that it’s just hopelessly outdated. A Charles Dickens inspired musical might have worked in 1968, but those were strange and terrible times in our nation’s history, and we just don’t have the drugs to get through shit like this anymore.
47. Chicago – 2002
It’s a musical! Starring Richard Gere! Next.
46. Driving Miss Daisy – 1989
It’s really more of a punchline than a beloved movie, isn’t it? Look, I love Morgan Freeman too, and he’s great in this, but Morgan Freeman would be awesome reading the phone book for two hours. That doesn’t mean it should win an Oscar.
45. The English Patient – 1996
When your movie’s biggest claim to pop culture fame is as a Seinfeld joke, things have taken a bad turn somewhere. And when that joke is that your movie is so goddamn long that no one can make it all the way through without falling asleep, it might be time to discuss some things with your editor.
44. Titanic – 1997
Look, you know it, I know it… this is probably the most overrated movie of all time. It became a sensation pretty much because every teenage girl saw it in the theaters 11,000 times which basically makes it the Justin Bieber of movies. Okay, that’s too mean, but you can’t deny that this is yet another movie that pretty much has become the butt of pop-culture jokes. Leo is probably embarrassed of this shit now. You know it’s true.
43. Terms of Endearment – 1983
The cast and crew make this much better than it should be, but let’s face it, it’s pretty much a juiced up Lifetime movie. Okay, that’s not fair. It’s definitely richer and more poignant than that, and anytime Jack Nicholson is involved you’re doing okay, but any movie that’s described as “the ultimate tearjerker” is treading on dangerous ground, and I can’t in good conscience go any higher for a movie that inspired the Nicholas Sparks’ of the world.
42. Forrest Gump – 1994
This is a weird one because if you adjust your expectations, it’s entertaining enough. But if you judge it by Oscar standards, than it falls apart. It’s ridiculous, corny and goddammit, there is no way you can tell me this deserved the Oscar in 1994. Pulp Fiction and The Shawshank Redemption were both right there! Come on.
41. Dances with Wolves – 1990
This has suffered a bit with time. First of all, Kevin Costner: creative visionary is evidence that we had lost our way as a people in 1990. Second, the “sensitive” plot is actually kind of offensive – it reinforces the “noble savage” trope while a white dude comes along and saves the day. Third, no one on Earth actually believes this should have won the Oscar over Goodfellas. At least no one I want to know.