New York City is arguably one of modern history’s greatest literary muses — Frank O’Hara extolled its dirty streets, Gay Talese marveled at the social order of its cats, and countless essayists channeled Central Park’s glory. Among Gotham’s many admirers was Jack Kerouac (March 12, 1922–October 21, 1969) — passionate teenage diarist, admonisher against popular opinion, sage of literature and life.

Somewhere between young Gay Talese’s New York: A Serendipiter’s Journey and E.B. White’s classic Here Is New York comes a chapter titled “New York Scenes” from Kerouac’s 1960 gem Lonesome Traveler (public library) — a kind of narrative emotional cartography of Manhattan, woven of fascinating sketches of Gotham’s vibrant life and cast of characters as recorded in Kerouac’s travel journals, written in his signature style of spontaneous prose, complete with his famous disdain for apostrophes.

He opens the chapter with a loving appreciation of his mother, a testament to parents’ power of cultivating genius and encouraging “horizontal identity”:

[M]y mother was living alone in a little apartment in Jamaica Long Island, working in the shoe factory, waiting for me to come home so I could keep her company and escort her to Radio City once a month. She had a tiny bedroom waiting for me, clean linen in the dresser, clean sheets in the bed. It was a relief after all the sleepingbags and bunks and railroad earth. It was another of the many opportunities she’d given me all her life to just stay home and write. I always give her all my leftover pay. I settled down to long sweet sleeps, day-long meditations in the house, writing, and long walks around beloved old Manhattan a half hour subway ride away. I roamed the streets, the bridges, Times Square, cafeterias, the waterfront, I looked up all my poet beatnik friends and roamed with them, I had love affairs with girls in the Village, I did everything with that great mad joy you get when you return to New York City.

Kerouac proceeds to invite us into the inner circle of the beatniks and their experience of the city:

My friends and I in New York city have our own special way of having fun without having to spend much money and most important of all without having to be importuned by formalistic bores, such as, say, a swell evening at the mayor’s ball. — We dont have to shake hands and we don’t have to make appointments and we feel all right. — we sorta wander around like children. — We walk into parties and tell everybody what we’ve been doing and people think we’re showing off. — They say: “Oh look at the beatniks!”

He then offers a guided tour of a beatnik’s New York, full of Kerouac-isms (“Men do love bars and good bars should be loved”) and irreverent romance (“…some romantic heroes just in from Oklahoma with ambitions to end up yearning in the arms of some unpredictable sexy young blonde in a penthouse on the Empire State Building.”) One by one he sketches out some of Manhattan’s most iconic places and faces, then takes us to the crown jewel of tourist attraction and ogles it with equal parts cynicism and awe:

What’s Times Square doing there anyway? Might as well enjoy it. — Greatest city the world has ever seen. — Have they got a Times Square on Mars? What would the Blob do on Times Square? Or St. Francis?

Next, he turns to the corner of 42nd Street and 8th Avenue, “near the great Whelan’s drug store,” to echo the eternal New Yorker’s lament over the city’s ever-changing landscape:

Across the street you can see the ruins of New York already started — the Globe Hotel being torn down there, an empty tooth hole right on 44th Street — and the green McGraw-Hill building gaping up in the sky, higher than you believe — lonely all by itself down towards the Hudson River where freighters wait in the rain for their Montevideo limestone. —

Gliding downtown for some night life, Kerouac takes us to the East Village to visit with some jazz legends and recounts a charming anecdote about his beatnik brother-in-arms, Allen Ginsberg, who once famously mistook Patti Smith for “a very pretty boy.”

The Five Spot on 5th Street and Bowery sometimes features Thelonious Monk on the piano and you go on there. If you know the proprietor you sit down at the table free with beer, but if you dont know him you can sneak in and stand by the ventilator and listen. Always crowded weekends. Monk cogitates with deadly abstraction, clonk, and makes a statement, huge foot beating delicately on the floor, head turned to one side, listening, entering the piano. Lester Young played there just before he died and used to sit in the back kitchen between sets. My buddy poet Allen Ginsberg went back and got on his knees and asked him what he would do if an atom bomb fell on New York. Lester said he would break the window in Tiffany’s and get some jewels anyway. He also said, “what you doin’ on your knees?” not realizing he is a great hero of the beat generation and now enshrined. The Five Spot is darkly lit, has weird waiters, good music always, sometimes John “Train” Coltrane showers his rough notes for his big tenor horn all over the place. On weekends parties of well-dressed uptowners jam-pack the place talking continuously — nobody minds.

He then turns to the party scene of the underground artists, socialites, and literary types. One of them, Leroi Jones, who self-published Yugen Magazine “on a little cranky machine and everybody’s poems are in it,” Kerouac describes as a “historic publisher, secret hipster of the trade” — an early use of “hipster” at the dawn of its popular coinage. But then, true to the rebellious beat spirit, he urges:

Let’s get out of here, it’s too literary. — Let’s go get drunk on the Bowery or eat those long noodles and tea in glasses at Hong Fat’s in Chinatown. — What are we always eating for? Let’s walk over the Brooklyn Bridge and build up another appetite. — How about some Okra on Sands Street? Shades of Hart Crane!

But the full vibrancy of Manhattan and its multitude of eccentric characters, the full range of the beatnik existence in the city that never sleeps, comes aglow under Kerouac’s gaze in the Village:

Ah, let’s go back to the Village and stand on the corner of Eighth Street and Sixth Avenue and watch the intellectuals go by. — AP reporters luring home to their basement apartments on Washington Square, lady editorialists with huge German police dogs breaking their chains, lonely dikes melting by, unknown experts on Sherlock Holmes with blue fingernails going up to their rooms to take scopolamine, a muscle-bound young man in a chap gray German suit explaining something weird to his fat girl friend, great editors leaning politely at the newsstand buying the early edition of the Times, great fat furniture movers out of 1910 Charlie Chaplin films coming home with great bags full of chop suey (feeding everybody), Picasso’s melancholy harlequin now owner of a print and frame shop musing on his wife and newborn child lifting up his finger for a taxi, rolypoly recording engineers rush in fur hats, girl artists down from Columbia with D.H. Lawrence problems picking up 50-year-old men, old men in the Kettle of Fish, and the melancholy spectre of New York Women’s prison that looms high and is folded in silence as the night itself — at sunset their windows look like oranges — poet e.e. cummings buying a package of cough drops in the shade of that monstrosity. — If it’s raining you can stand under the awning in front of Howard Johnson’s and watch the street from the other side. Beatnik Angel Peter Orlovsky in the supermarket five doors away buying Uneeda Biscuits (late Friday night), ice cream, caviar, bacon, pretzels, sodapop, TV Guide, Vaseline, three toothbrushes, chocolate milk (dreaming of roast suckling pig), buying whole Idaho potatoes, raisin bread, wormy cabbage by mistake, and fresh-felt tomatoes and collecting purple stamps. — Then he goes home broke and dumps it all on the table, takes out a big book of Mayakovsky poems, turns on the 1949 television set to the horror movie, and goes to sleep. And this is the beat night life of New York.

Lonesome Traveler, Kerouac’s first authentically autobiographical work, is an endless delight in its entirety. Complement it with Anaïs Nin on the poetic of New York and Sylvia Plath’s notorious New York summer.