Ryan Night’s Top 100 Movies: 50-41

Continuing right along with the top 100 movies of all time, here is 50-41.

For 100-91, click here.
For 90-81, click here.
For 80-71, click here.
For 70-61, click here.
For 60-51, click here.
For 40-31, click here.
For 30-21, click here.
For 20-11, click here.
For 10-1, click here.

50. A Clockwork Orange
A dark, dark, disturbing movie about a twisted society and the twisted people who succeed in it. The plot follows around a gang of hooligans led by a young sociopath named Alex, who terrorize their neighborhood and commit brutal crimes. Alex, an incarnation of evil, gets wrapped up in the political machinations of the upper class, whose own sociopathy and evil is revealed.

49. Into the Wild
A sensitive young man has a good look at what society has to offer and rejects it wholesale, preferring to go live alone in the wild. Unfortunately for him, the old adage that lone wolves don’t survive the winter turns out to be true. However, the movie breathes life into his bohemian dream and you can feel the purity of his yearning for freedom and a less offputting society.

48. Dogma
Ben Affleck and Matt Damon play exiled angels who are forced to live in the mortal world and interact with humans as punishment for transgressions against God until they come across a loophole that will let them return to heaven. This is a very interesting, funny and original movie, and I found Matt Damon and Ben Affleck to be compelling in their roles. The casual theology in the movie is also highly engaging.

47. Gangs of New York
Of all the Martin Scorsese movies (and I’ve seen a ton of them: Goodfellas, The Departed, Taxi Driver, etc, etc.), this is the one I want to put on my top 100 movies of all time list, even though it almost certainly isn’t objectively the ‘best’ one. Leonardo DiCaprio is an Irish immigrant to turn of the century, Tammany Hall era New York, where tensions between the nativists and the immigrants are boiling. What’s really profound about this movie is the relationship between DiCaprio and his nemesis, the Butcher, who killed his father years earlier. DiCaprio ends up joining the Butcher’s gang to get close to him and rises through the ranks to become his lieutenant. The cocktail of emotions these two opposing forces have for one another makes for a powerful and complex screen relationship: respect, hatred, love, rage. In a way, it’s a movie about perfectly suited rivals for two people predisposed to elevate their rival to the highest point of focus and affection. Very interesting movie. Great set pieces. Cameron Diaz is terrible in the movie.

46. Se7en
Another movie that most assuredly belongs on my top 100 movies of all time, and probably anybody’s, this thriller starring Brad Pitt and Morgan Freeman has two cops chasing around a serial killer who is modeling his murders after the Christian seven deadly sins, as a critique of society. The killer, John Doe (played by Kevin Spacey), is off the charts creepy and evil to the point I think in the world of the film people may have believed if he said he was an actual demon. It’s a hard movie to look away from, because it masterfully utilizes suspense and mystery, and as grotesque and horrific as the crimes are, they’re bizarrely creative, which sort of forces you to confront them. It has, perhaps, one of the most iconic film endings of all time. Twisted movie.

45. The Big Lebowski
You may realize by now there are several Coen Brothers movies on this top 100 movies of all time list. In fact, in this section alone, there are two (that brings us up to, I think, 4 total by this point). I’m a big Coen Brothers movie. I’ve watched every single one, including their student film Blood Simple. Which was not that good but, better, I’m sure, than I would have done with a student film. What to even say about this movie? It’s iconic. Jeff Bridges plays ‘The Dude’, it spawned a number of interesting film essays about the generational interplay between the core group of 3 ( Jeff Bridges, John Goodman & Steve Buscemi), it’s full of memorable quotes and scenes. This movie is a heavyweight.

44. Forgetting Sarah Marshall
A hilarious movie and a fantastic breakup movie for men. Often, if you’re a guy, the film trilogy you get prescribed after a breakup is Forgetting Sarah Marshall, High Fidelity and Swingers. The plot goes that Kristen Bell dumps Marshall from How I Met Your Mother because she’s been cheating on him with Russell Brand, but surprise surprise, they all end up in Hawaii together. Marshall gets over Kristen Bell, eventually hooking up with Mila Kunis and he fulfills his dream of staging a musical love story about Dracula. Hilarious movie from beginning to end.

43. O Brother Where Art Thou
Another Coen Brothers movie, this time is a movie starring George Clooney, which is interestingly loosely based on Homer’s The Odyssey reimagined as a Mark Twain-era American folk tale. George Clooney and his little group escape from prison and begin making their way across the country to stop George’s wife from marrying another man. On the way they meet several obstacles including sirens, a Cycloptic John Goodman, etc. Man of Constant Sorrow is probably my favorite film soundtrack standout song of all time.

42. 1984
I didn’t think much of this movie or the book it was based on when I was first exposed to them in my teens, but it’s unexpectedly become the most important piece of cinematic and literary canon to me that I can think of. This story was prescient. Everything this story predicted is shockingly relevant to modernity. Oligarchical Collectivism, an uninformed, easily manipulated population capable of switching animosity from one geopolitical foe to another at a moment’s notice even if the rationale is totally illogical, stark social class hierarchies, in-home 24/7 surveillance by the upper classes on the lower classes, severe social rules enforced by ostracisation and loss of social status, the list goes on and on. Watch this movie if you want to scare yourself with how 1984 was released almost 80 years ago, perfectly accurately predicted 2019, and did so predicting it starkly as a terrifying dystopian hellscape. This movie should be higher on this list, but I hesitated to put the movie version of a book on the list at all, so its impressive feat is being on two lists.

41. Donnie Darko
In high school this was, hands down, my favorite movie. I’m not 100% sure I’d want to watch it now, I think I’ve absorbed what I could absorb from this movie and related to it at exactly the right time period, but nevertheless it’s a great movie about alienation, isolation, mental health, time travel, the grotesqueness and arbitrary nature of normalcy and it’s just plain a weird, cool movie. It was a big influence on me.

That does it for 50-41 of the top 100 movies of all time list.

For 100-91, click here.
For 90-81, click here.
For 80-71, click here.
For 70-61, click here.
For 60-51, click here.
For 40-31, click here.
For 30-21, click here.
For 20-11, click here.
For 10-1, click here.