Frank Sinatra famously declared that he felt sorry for people who don’t drink, ’cause when they wake up in the morning, that’s the best they’re going to feel all day. I’d bet most writers — whether novelists, journalists, poets or Book Riot contributors — would agree. Indeed, the annals of literary history are as booze soaked as a frat house basement floor. So, since the Johnny Depp movie-ization of The Rum Diary — famous boozer Hunter S. Thompson’s novel about “violent alcoholic lust” — came out last week, let’s take a short, rather incomplete look at the good and bad, the ups and downs (that’s how it always is with drinking, right?) of the often funny, sometimes violent, but always entertaining relationship between booze and books.

GOOD: Let’s start with an easy one. Ernest Hemingway is, of course, the poster child of the drunken writer. You already know Papa’s story, but let’s let Modern Drunkard magazine explain in more detail.

BAD: Booze was probably the main reason the back of Hemingway’s skull made more than a passing acquaintance with a shotgun bullet.

GOOD: Charles Bukowski, most notably his novels Ham on Rye and Factotum. These are two of my favorite booze-(un)centered books of all time. Really, they’re thinly veiled memoirs in which the main character, Henry Chinaski (Bukowski’s alter ego), navigates his way through life in a near-constant drunken stupor. They’re great! Also, Factotum was adapted into a delightful little film starring Matt Dillon and Lili Taylor.

BAD: Truman Capote’s drunk voice (well, his sober voice, too, if Philip Seymour Hoffman’s portrayal is accurate), and this quote: “I drink, because that’s the only way I can stand it.” Pull it together, man!

GOOD: Kerouac, Burroughs, Ginsberg. Admittedly, these fellas were abusing more than just booze, and while they did produce some wonderful literature, they also are responsible for some terrible facial hair trends. (Thus their failure to make our list of Awesome Literary ‘Staches.)

BAD: F. Scott Fitzgerald died at age 44 after a life of alcoholism. “First you take a drink, then the drink takes a drink, then the drink takes you,” he said. Indeed.

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GOOD: This quote by famously drunk Raymond Chandler: “Alcohol is like love. The first kiss is magic, the second is intimate, the third is routine. After that you take the girl’s clothes off.”

BAD: After several drinks, I once tried to pick up a girl in a bar by telling her she looked like Zadie Smith. Not only did she have no idea who Zadie Smith is, she thought I was insulting her. Swing and a miss!

GOOD: There is a definite dearth of alcoholic women writers. Dorothy Parker is one. I can’t think of (read as: find via Google) another. Can you?

BAD: There is a definite dearth of alcoholic women writers.

Finally, if you’re interested in a fairly reasonable explanation for why so many writers are alcoholics, this is from the book Alcohol and the Writer, by Donald Goodwin, who is head of the Kansas State University Psychiatry department:

Writing involves fantasy; alcohol promotes fantasy. Writing requires self-confidence; alcohol bolsters confidence. Writing is lonely work; alcohol assuages loneliness. Writing demands intense concentration; alcohol relaxes.

What has slipped my memory here? What are your favorite booze/book moments? Please comment!

And, now, it’s time for a drink. In the immortal words of Homer Simpson: “To alcohol! The cause of, and solution to, all of life’s problems.”