Every year on or around March 12th, acolytes of the Beat writer Jack Kerouac cluster at the Flamingo Sports Bar in St. Petersburg, Florida, to celebrate his birthday. Kerouac would have turned ninety-six this week had he not died just three blocks south, at St. Anthony’s Hospital, on October 21, 1969. The official cause was an abdominal hemorrhage, made fatal by several decades of ferocious drinking. He was forty-seven.

Two local acolytes, Pat Barmore and Pete Gallagher, have been organizing Jack Kerouac Night at the Flamingo for five years. Folk and jazz musicians play short sets, while poets read from battered notebooks. (Sometimes, in true Beat style, both things happen at once.) Patrons are encouraged to toss back “a shot and a wash,” Kerouac’s preferred tipple. (When I texted a friend in New York a picture of a menu board displaying the price of the Kerouac Special—two dollars and fifty cents for a whiskey and a plastic cup of beer—he texted back, “That should be illegal!”) The Flamingo, which opened in 1924, is more of a pool hall than a literary salon. A sign warns against gambling, profanity, lifting tables, throwing pool balls, and snapping sticks. Regulars, who tend to be over forty, gather at the bar to light each other’s cigarettes and discuss the weather. Kerouac’s novels are displayed on a rail in a side room. A mural, of him wearing a red plaid shirt and poking a cue ball, has been painted on the south side of the building. I liked the place immediately.

“The ghost of Jack Kerouac is definitely here,” Barmore announced at the start of the evening. The previous Sunday, he added, all of Kerouac’s novels “leapt off the shelf and fell on the ground,” apropos of no apparent stimuli. A similar event had recently occurred at Haslam’s Bookstore, a few miles away on Central Avenue. Per local lore, Kerouac used to wander into Haslam’s and rearrange his own books, jockeying for better and more prominent shelf placement; supposedly, this still goes on. A couple dozen people crowded the room. The guitarist Big Jim Mason opened the show with a handful of original folk songs. He was wearing a black T-shirt that promised, “It’s not a wrong note, it’s jazz.”

At a certain point in a person’s life, liking Kerouac—and liking “On the Road,” especially—becomes embarrassing. It’s not a particularly enlightened book. While there are a handful of female characters in it, these women are largely unrecognizable as human, and to say that Kerouac was inelegant about matters of race is generous. The plot isn’t particularly riveting. A disenchanted and heartbroken dude named Sal Paradise meets Dean Moriarty, a charismatic raconteur (he was inspired by Kerouac’s real-life friend, the poet-madman Neal Cassady) who strives for absolute liberation, no matter the emotional cost. Paradise buys it: “Somewhere along the line I knew there would be girls, visions, everything; somewhere along the line the pearl would be handed to me.” Together they crisscross North America, hot for adventures.

I love “On the Road,” despite knowing very well that it’s a fantastical and likely toxic account, blind to both engines of privilege and the sacrifices inherent to endless meandering. Any ongoing affinity for the book is a way of signalling to the world that you are still enthralled by juvenile and illusory notions of freedom. Yet I’m nonetheless cowed by the rhythm and the elegance of Kerouac’s prose, how he taps into the wild energy of adolescent wanting. I was a brooding and sullen high-school freshman when I first read “On the Road,” still doing the hard and complicated work of figuring out how I fit into the world. It seems apt that the most quoted line from “On the Road” suggests we simply give in to our longings. To do otherwise is cowardly (or, worse, boring): “ . . . the only people for me are the mad ones, the ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones who never yawn or say a commonplace thing, but burn, burn, burn like fabulous yellow roman candles exploding like spiders across the stars and in the middle you see the blue centerlight pop and everybody goes ‘Awww!’ ”

The book was (supposedly) written on one continuous, hundred-and-twenty-foot scroll of typing paper—a savage and unmediated burst. In 1959, Kerouac told the talk-show host Steve Allen that it took him three weeks, although this, too, was later revealed to be an ingenious bit of self-mythologizing. (It turns out nothing shatters the glamour of genius more quickly than admitting that you spend hours every day moving commas around, or swapping out adverbs for different adverbs.)

“Kerouac cultivated this myth that he was this spontaneous prose man, and that everything that he ever put down was never changed, and that’s not true,” the Kerouac scholar Paul Marion told NPR, in 2007. “He was really a supreme craftsman, and devoted to writing and the writing process.” The book went through several drafts between 1951 and 1957, when Viking Press finally published it.

Kerouac was considered childish even in his lifetime. His obituary in the Times—it was written by Joseph Lelyveld, who decades later became the executive editor of the paper —throbs with a vague disdain. Lelyveld refers to the Beat Generation as “a bizarre bohemian phenomenon confined to small coteries in San Francisco and New York” and points out that critics of Kerouac’s work “found something ludicrous in his search for sensation and instant salvation on the byways of America.” He even refers readers to “On the Sidewalk,” a satire by John Updike that ran in this magazine, in 1959. (The punch line is, “But what do they mean grown up? I’m thirty-nine now?”)

Yet the way that novel is so enduring—so impervious to shifting cultural winds—seems to indicate something about how successfully it articulates a very American rootlessness. I don’t mean our seemingly inborn (and now faded) frontier instincts—a hunger to keep charging at the horizon, scouting greener pastures—but, rather, some implacable desire to be of nowhere, and indebted to nothing. “It is the fundamental contradictoriness of the United States of America—the illogical but optimistic notion that you can create a union of individuals in which every man is king,” Susan Orlean writes, in “The Orchid Thief.” Americans tend to be obsessed with freedom and self-determination. Notions that would seem selfish and unsatisfying to other cultures are treasured here. Concede nothing and be beholden to no one: “Do You.”

It wasn’t until much later in my life that I recognized Kerouac’s thrashing as gendered: the book is a hysterical elegy for threatened male freedom, and a siege against feminized domestic routines. Staying in one place—giving your life over to a single person or landscape—is akin, he suggests, to spiritual death. Instead, men ditch clingy women for the company of other men, and the freedom they allow each other. “On the Road” might be the last great American novel about masculine seduction.

Kerouac had just turned twenty-nine when he started writing the book in earnest. Most covers of “On the Road” feature a grainy, black-and-white photograph of a young Kerouac looking rakish and cavalier. Sometimes, like on the Penguin edition, from 1994—my first copy—he’s leaning against a brick wall and smoking.

By the time Kerouac moved to St. Petersburg, in 1966, he was a different kind of man: chubby and discontent, living with his mother and his third wife in an unremarkable one-story home with a screen door and an overgrown concrete walkway. It had been his mother’s idea to move to Florida. She thought the mild weather might be good for her health. (Kerouac was born and raised in Lowell, Massachusetts.) Kerouac occasionally dragged a cot into the back yard and slept there. I imagine it felt good, lying shirtless in that thick, humid air. Florida has long been a beacon for oddball scoundrels seeking refuge of one sort or another. The atmosphere can return a person to some wet and primal place.