Just today I was talking with two Mormon missionaires and one of them asked me about my hat: What does “The Color Purple” mean?
I was totally dumbfounded! They had never heard of the book, movie, or musical!
Books (and movies and plays) you should be familiar with in order to converse well in modern society
I don;t think that was original with the film.
Got it. OK, there are some good recommendations above, but you’re going to need a few more (I’m restricting myself to literature here, and assuming the conversations will be in English). Off the top of my head, here are a few.
The Bible and Shakespeare have been mentioned.
You’re going to want at least a passing familiarity with Homer’s *Iliad *and Odyssey (I’ll bet you’ve heard “beware of Greeks bearing gifts,” or of Scylla and Charybdis and the Trojan horse, at least once, or heard something described as “Homeric”).
Some knowledge of Charles Dickens would be useful.
A working knowledge of Greek myths and legends (ever here something described as “Herculean”, or Sisyphean"?). Hesiod’s *Works and Days *and *Theogony * is a good source for a lot of stuff.
A basic knowledge of some Roman history. The histories of Tacitus or Suetonius will do nicely. Someone mentioned I, Claudius above – this is where Graves got his material.
Orwell (or at least one of his books) was mentioned in the OP. In addition to 1984, you should also read Animal Farm.
Dante is essential, especially the Inferno.
A collection of Arthurian legends would be a good read.
You don’t have to read the whole collected works of Aristotle and Plato, but their writings are pretty foundational documents for Western civilization, and you’ll come across references to them pretty regularly.
I’ll bet that I think of a dozen more in the next hour, but that’s what comes to mind immediately.
One time I was talking with my boss about a particularly horrid assignment that his boss had given me, where I had to build a team of folks to do … something … all while folks had their day jobs. As expected, unless I nagged everyone, all progress stopped.
I described this as a Sisyphean task, and he had no clue what I was talking about.
Oh yes… Another boss gave me a blank stare when I described a particular problem as a Prisoner’s Dilemma. I’m not sure how common that book is to read, but it is on my bookshelf.
Why this? I’m aware that it’s a great book, and I’ve been told that it’s very helpful in learning Roman history, but what parts of it do people famously reference? 
To be culturally literate WRT Faust you should know that there’s more than one “it” to read. The two best-known are Marlowe’s play and Goethe’s opera. The former is short and easy to read (if you have an annotated edition). The latter’s more of a challenge.
Some more answers to the OP:
The Graduate
Catch-22
Apocalypse Now
MASH
Rocky
Planet of The Apes
The Tipping Point
The Foutainhead
Atlas Shrugged
The Ten Commandments
The Manchurian Candidate
Marathon Man
The French Connection
Dirty Harry
The Good, The Bad, and The Ugly
Rainman
The Iliad and The Odyssey
A few books about the founding of the U.S.A.
Something on Einstein. And Newton.
The Birds
Psycho
Saving Private Ryan
Twelve Angry Men
Star Trek
Blazing Saddles
Minority Report
Silkwood
Roots
In the Heat of The Night
The Right Stuff
The Electric Koolaid Acid Test
Fear and Loathing in Las Vegas
Butch Cassidy & The Sundance Kid
Shane
Bonfire of The Vanities
The Great Escape
Bullit
Cool Hand Luke
Death Wish
Animal House
Silence of the Lambs
Goldfinger
The Shining
Obviously, the books where possible.
Why? Some of these are much better known as movies. A person who’s read Robert Bloch’s Psycho but is unfamiliar with Anthony Perkins’ portrayal of Norman Bates (and Bernard Herrmann’s score!) is arguably less culturally literate than vice versa.
Going by movies I hear quoted most often not only among my circle of friends but also generally among Americans under the age of 30, it would be difficult to follow a typical conversation without a working knowledge of the one-liners in Anchorman.
You’re right. I agree with that. I didn’t mean to insinuate such a hard line. But the book versions of Fear and Loathing, The Fountainhead, and Bonfire, for example, are unquestionably superior to their film versions. While Goldfinger, to your point, is much more a part of the culture through the film.
You make a point. But it does teach us quite a bit Roman history.
All of these,* esp Dante *can be read in a summary version, or even the wiki page. ;)Hell, even a good kids book might do for the myths.
Enniaunus: I have never known anyone to use any of the lines from Anchorman, unless it was in a line that existed prior.
Well, yes, but then you won’t really understand the references. You’ll know what people are referring to, but you won’t have the context. Besides, they’re all well worth reading. And Dante, in a good translation, is absolutely wonderful.