Start here with Adler's "Great Books."

https://thinkingasleverage.wordpress.com/book-lists/mortimer-adlers-reading-list/

What comes to my mind right away is that there is no neutral answer to this question. If I give you my favorite books, then I give you my own sense of the heroic and the profound.

That said, I personally would advise others to follow their own sincere response. It's pointless to read some famous book if it is not moving you and therefore changing you. If you find an author/book that moves you, it's a good bet that it is linked in an obvious way to other books/authors that will move you.

At the moment I'm thinking Groundless Grounds packs quite a punch. That kind of thinking helps keep the philosophically inclined from being seduced by artificial systems that would otherwise cut them off from a fuller vision of human reality.

Contemplate for a moment the difference between ignorance and stupidity. From ignorant to well read one passes by way of reading some good books; From stupid to sensible is a much harder road, and magic is required.

Pirsig is magic, and Lila is even better than Zen and the Art. Winnie the Pooh is magic; Pobby and Dingan, Spoonface Steinberg, The Little Prince, If This is a Man, Lao Tsu, Philip Dick, Ursula LeGuin, Faulkner - start with Light in August, Dostoevsky, start with The Brothers Karamazov, J. Krishnamurti, start with The Ending of Time, The Cloud of Unknowing, The Gospel of St John.

Generally, I would say that a good stock of magic is the best defence against the stupidities of philosophy, of which there are many, and philosophy is the best defence against the stupidities of religion and politics, of which there are also many.

there is no neutral answer — macrosoft

Who would want a neutral answer? Neutral is stupid! Powerful cannot be neutral, it acts.

Edit: Steinbeck, how could I forget? Cannery Row, and his unfinished masterpiece, The Acts of King Arthur, and The Grapes of Wrath, of course.

Have a look at The Western Canon.

Pick a book you wish to read and understand. Start reading that book, when you come across a reference to an unfamiliar work or concept, stop reading and go read the related work. Do this every time you run across something unfamiliar. While also making sure to study the culture and time period the work was written in.

Soooo many books, soooo little time. Be aware that you can read a lot and still be stupid, and read sparingly and be quite wise.

Start and stick with the classics. should you read Shakespeare? Don't know. There are other writers contemporary with Shakespeare who wrote some awfully good stuff. Like Love III by George Herbert b. 1593) Just three stanzas. Read often.

James Boswell b. 1740 (dictionary compiler Samuel Johnson's biographer) wrote great prose. In one case (from his Journals) he tried to save a fellow condemned to hanging for theft (this was the 18th century) by attempting to revive the unfortunate fellow after the hanging. Didn't work.

Don't miss Samuel Pepys' diary (b. 1633) for a candid report on the daily affairs of a man on the make.

Tolkien. LeGuin. Many works of science fiction. The short stories of Flannery O'Connor. Emily Dickinson. Henry James. Kurt Vonnegut.

Mary Anne Evans, aka George Eliot is one of the best Victorian novelists, imho. Dickens, of course.

Hawthorne, Poe, Steinbeck, Philip Roth, Thoreau, some of Walt Whitman (his long poems are a bit much today). Sample stuff from the beats: Some of Alan Ginsberg's poetry is magnificent.

I saw you, Walt Whitman, childless, lonely old grubber,
poking among the meats in the refrigerator and eyeing the grocery
boys.
I heard you asking questions of each: Who killed the
pork chops? What price bananas? Are you my Angel?
I wandered in and out of the brilliant stacks of cans
following you, and followed in my imagination by the store
detective.
We strode down the open corridors together in our
solitary fancy tasting artichokes, possessing every frozen
delicacy, and never passing the cashier.
... — Allen Ginsberg

Is Cormac McCarthy a great writer? Don't know, but his The Road was one of the most unforgettable apocalypse stories I have read.

How about On the Road by Jack Kerouac? Moderately interesting.

Margaret Atwood's Madd Addam trilogy; the Handmaid's Tale.

on and on.

How about On the Road by Jack Kerouac? — Bitter Crank

That was the book of which Truman Capote said 'that's not writing, that's typing'.

I'm inclined to agree.

Classic, that was my first.. changed my life, made me decide to study a degree in philosophy. I don't know why it is so appealing. Perhaps the way he applies the theory of philosophy to instances of life itself in the form of a narrative. Something which i think most common people suffer with when trying to assess the value and utility of philosophy (usually before being scared away by an apparent complexity of words and therefore leads to a subconscious decision to label it all as "useless obfuscating time-wasting nonsense" so that they remove the confusion they feel by allowing them self to feel justified in not having to see value in any of it)

That was the book of which Truman Capote said 'that's not writing, that's typing'. — Wayfarer

Truman Capote was a much better writer, certainly. I read Kerouac's book as part of a short course in beat literature I was offering myself. I found it interesting, useful for getting the feel of the beat period, and was glad to cross it off my list of books I should have read by now. It was OK. I've tried reading a number of Burroughs's books, with mixed results. The first one I read was The Ticket that Exploded, which was back in about 1967. I didn't get it in '67. Don't know that I got it in 2017, either.

I've come to like Allen Ginsberg's beat period better.

...who broke down crying in white gymnasiums naked
and trembling before the machinery of other
skeletons,
who bit detectives in the neck and shrieked with delight
in policecars for committing no crime but their
own wild cooking pederasty and intoxication,
who howled on their knees in the subway and were
dragged off the roof waving genitals and manu-
scripts,
who let themselves be fucked in the ass by saintly
motorcyclists, and screamed with joy,
who blew and were blown by those human seraphim,
the sailors, caresses of Atlantic and Caribbean
love... — Allen Ginsberg

and so on. Howl. Had I read this poem in 1964, when some sections of English lit 110 were focussing on the beats, I would have been shocked, appalled, and totally fascinated. Much better that I read it later when I could appreciate it, when I had had enough sex & life experiences to know what he was talking about, when I had finally aged past those sorts of joyful activities...

There is a lot to be said for NOT reading some books too soon.

"Going from stupid to well-read, what essential classics would get a person there fastest?"

Start by calling yourself ignorant instead of stupid. That always helps.

Isaac Asimov - The foundation Collection
Daniel C. Dennett - From Bacteria to Bach and Back
Daniel Klein - Every Time I Find the Meaning of Life
Lawrence Krauss - The Greatest Story Ever Told--So Far Why Are We Here

Hannah Arendt - The Human Condition [political philosophy]
Andre Leroi-Gourhan - Gesture and Speech [anthropology]
Alicia Juarrero - Dynamics In Action: Intentional Behavior as a Complex System [systems science]
Alva Noe - Action in Perception [philosophy of mind]
Eva Jablonka and Marion Lamb - Evolution in Four Dimensions [evolutionary biology]
Daniel Dor - The Instruction of Imagination [linguistics]
Raymond Geuss - Changing the Subject [philosophy]
Giovanni Arrighi - The Long Twentieth Century [political economy]
Leo Panitch and Sam Gindin - The Making Of Global Capitalism: The Political Economy Of American Empire [political economy]
Eric Hobsbawm - The Age of Revolution/Capital/Empire/Extremes (tetraology) [history]
Fernand Braudel - Civilization and Capitalism, 3 Vols. [history]

Missing some sociology, literature, and art, but not familiar with anything that's general enough.

There is a lot to be said for NOT reading some books too soon. — Bitter Crank

Hear hear...

You didn't mention the subject(s) you want to be "well-read" in. People who may be "well-read" in literature, may know nothing about mathematics, physics, chemistry, engineering, etc. If you want to learn a specific subject like mathematics or physics, then you'll need to read actual textbooks and go through the problem sets.
If you want to learn to reason well in general, then you should study math, including non-computational areas like mathematical logic, real analysis, etc. where you can engage in proofs, which are simply logical arguments.
If you want a great book on general philosophical issues that is off the beaten path a bit, but a real life changer for those who go through the book, and actually think about it, the best book I can recommend is "The Tao is Silent" by the late, great, Raymond Smullyan.

the late, great, Raymond Smullyan. — LD Saunders

Definitely. Logic and magic.

Unenlightened: You are the first person I've run across on line who knows who Raymond Smullyan was. It was a sad day when he passed away. I was hoping he'd live past a hundred.

Generally, I would say that a good stock of magic is the best defence against the stupidities of philosophy, of which there are many, and philosophy is the best defence against the stupidities of religion and politics, of which there are also many. — unenlightened

What is the best defence against the stupidities of science?

What is the best defence against the stupidities of science? — Evil

Alas, the stupidities of science are lethal, and I have no defence to offer.

Time for a new discipline