Here are my personal top 5 favorite books in the order in which I discovered them.

1. Walden, Henry David Thoreau

I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived. I did not wish to live what was not life, living is so dear; nor did I wish to practise resignation, unless it was quite necessary. I wanted to live deep and suck out all the marrow of life, to live so sturdily and Spartan-like as to put to rout all that was not life, to cut a broad swath and shave close, to drive life into a corner, and reduce it to its lowest terms, and, if it proved to be mean, why then to get the whole and genuine meanness of it, and publish its meanness to the world; or if it were sublime, to know it by experience, and be able to give a true account of it in my next excursion.

I discovered him in high school along with Ralph Waldo Emerson (after whom I named one of my kids). Both of these guys blew my mind then and still do. Of everything Transcendental I’ve read, Walden is the most accessible and practical and appeals to both my intellectual and emotional side. Someday I will write an essay entitled “Why I Am Not a Transcendentalist,” but I still derive much meaning and pleasure from their writings and lives.

2. Lord of the Rings, J.R.R. Tolkien

All we have to decide is what to do with the time that is given us.

I also discovered Tolkien in high school through The Hobbit. If it wasn’t for Lord of the Rings, then that book would be at this spot. The scope of Rings is so grand that it is not only an immersive masterpiece of fiction, but offers insight into so many areas of life: political philosophy, ethics, linguistics, literary theory, etc.

3. Moby-Dick, Herman Melville

Know ye now, Bulkington? Glimpses do ye seem to see of that mortally intolerable truth; that all deep, earnest thinking is but the intrepid effort of the soul to keep the open independence of her sea; while the wildest winds of heaven and earth conspire to cast her on the treacherous, slavish shore?

But as in landlessness alone resides highest truth, shoreless, indefinite as God—so, better is it to perish in that howling infinite, than be ingloriously dashed upon the lee, even if that were safety!

Whenever I read that I want to stand up and shout “Yes! YES!” like Rodney Dangerfield in Back to School. I should be memorizing passages of this book like Bible verses. To put it anachronistically, this is the atheistic, seafaring American Lord of the Rings written 100 years earlier. Like Ishmael:

Whenever I find myself growing grim about the mouth; whenever it is a damp, drizzly November in my soul; whenever I find myself involuntarily pausing before coffin warehouses, and bringing up the rear of every funeral I meet; and especially whenever my hypos get such an upper hand of me, that it requires a strong moral principle to prevent me from deliberately stepping into the street, and methodically knocking people’s hats off—then, I account it high time to get to sea as soon as I can.

4. Leaves of Grass (1st Ed.), Walt Whitman

I depart as air, I shake my white locks at the runaway sun, I effuse my flesh in eddies, and drift it in lacy jags.

I bequeath myself to the dirt to grow from the grass I love, If you want me again look for me under your boot-soles.

You will hardly know who I am or what I mean, But I shall be good health to you nevertheless, And filter and fibre your blood.

Failing to fetch me at first keep encouraged, Missing me one place search another, I stop somewhere waiting for you.

I specify the 1st edition because it is a single, unified work dating from the outset of Whitman’s career. More common is the “Deathbed” edition from the end of his life which is quite different (ie. more discursive and diluted). It was inspired by an essay of Ralph Waldo Emerson‘s and Whitman sent him a copy when it was first published. I love Whitman’s celebration of personal experience and individualism.

5. Pride and Prejudice, Jane Austen

There are few people whom I really love, and still fewer of whom I think well. The more I see of the world, the more am I dissatisfied with it; and every day confirms my belief of the inconsistency of all human characters, and of the little dependence that can be placed on the appearance of merit or sense.

Elizabeth Bennet is the best character in all of English literature. You know that “what if” game where you imagine dinner with a favorite fictional character, historical figure, etc.? Mine would be having ice cream in the park with Lizzie and making fun of people who walk by. I love Lizzie Bennet. Don’t tell my wife.

This book is flawless. The characters are the realest real people ever to be not really real. The plot is more or less cliche (at least to moderns who have lived in this novel’s wake), but the characters are so fully formed and the writing is so good that you believe that these characters are making their own actual choices and are not mere puppets in the hands of the writer with an agenda. Instead, these are real people who just so happened to live this perfectly cliched life.