The 5 Books On My Prison Reading List

The addictive new program Orange is the New Black, based on the 2011 memoir by Piper Kerman, humanizes the setting of a women’s correctional facility. It’s easy to binge watch this “guilty fish-out-of-water” series and wonder, How would I react to a  prison stint? Now, clearly, prison is a dehumanizing and horrendous experience that, in real life, none of us would ever want to experience. But from a strictly dream world, glass-half-full, Ned Flanderian perspective, a minimum security correctional facility could be viewed as an opportunity to finally read all those books the unrelenting rigors of daily life have led you to ignore. Such as…

1. Ulysses, by James Joyce
I’ve never read Ulysses. A weathered copy mockingly resides on my bookshelf as a daily reminder of unfulfilled intentions. Perhaps I shouldn’t display the book so prominently, but I enjoy implying that I’ve read the classic novel/giant paperweight. “You’ve read Ulysses!” my house guest will say when s/he invariably notices the mammoth novel. “Well, has anybody truly read James Joyce?” I’ll vaguely retort with a hint of secret shame as I feebly attempt to change the subject to topics more in my wheelhouse, like Saved by the Bell trivia, third place spelling bee trophies from elementary school, or macaroni and cheese.

2. Atlas Shrugged, by Ayn Rand
Atlas Shrugged is widely recognized as one of the most influential (and controversial) books ever written, which makes it an ideal first selection for your prison book club. It’s the literary equivalent of challenging the most intimidating person in prison to a fight on your first day. When you whip out your copy of Atlas Shrugged, you’re saying “I’m willing and able to reference complex philosophical issues, correctly use the word ‘perspicacity,’ and perhaps even throw in a Socrates quote or two.” This novel will help you prove that knowledge is power. Also, power is power, so don’t forget your push-ups in between chapters.

3. War and Peace, by Leo Tolstoy
A perennial entry on scholarly top 10 lists, War and Peace is a daunting 1,200 page literary mountain, which roughly equates to about 10 Goosebumps books—and it’s difficult to ignore such provocative titles like Say Cheese and Die! or The Werewolf of Fever Swamp in favor of a challenging masterpiece. I would never have the temerity to read a Goosebumps novel in prison—they’re too scary and ripe for thievery. So if I ever find myself dancin’ to the jailhouse rock, I’m choosing the talented Mr. Tolstoy as my partner.

4. Walden, by Henry David Thoreau
What better way to hone your self-reliance than to read Thoreau’s renowned account of simple 19th century living near Walden Pond? Thoreau took a respite from the modern world to “live deliberately and front only the essential facts of life.” It’s quite the relateable impulse. Every day I daydream of taking an impromptu sojourn when my DVR forgets to record Conan or my YouTube video freezes. We’re both individualists—Thoreau with his critically acclaimed spiritual journey and me with my rarely updated blog that delves into the arcanum of 80s television theme songs. Two sides, one coin.

5. Zen and the Art of Motorcycle Maintenance, by Robert M. Pirsig
I attempted to read Zen and the Art of Motorcycle Maintenance in college, but instead chose to reread a book titled Poor Life Decisions a couple of dozen times. Looking back on my old copy of Zen, I found that I had underlined a specific passage:

“There is no perfectly shaped part of the motorcycle and never will be, but when you come as close as these instruments take you, remarkable things happen, and you go flying across the countryside under a power that would be called magic if it were not so completely rational in every way.”
This is why I’ve always been a proponent of underlining insightful passages in your books. It’s a way for your past self to communicate with your future self. Plus, if you loan a book to a friend, it’s a fun way to subtly publicize the fact that the guy who drinks chocolate milk through a fun, twisty straw may possess a hidden, pensive side to his personality.

Which books would you like to read in the unfortunate event of your incarceration?