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Under the Influence of Kerouac: On the Road Retrospective

On the Road by Jack Kerouac was one of the breakout novels of its time. The book still sees robust annual sales of 120,000 – 130,000 paperbacks of various editions.[1] Widely considered the father of the Beat Generation (or at least miscredited as the coiner of the term), Kerouac populates his novel with untamed characters straight out of his bohemian reality. He provides them with the cover of new names – although everybody knew who they were at the time – and describes their lifestyle as one the world comes to know as Beat. “The word ‘beat’ itself was almost exclusively used after World War II by jazz musicians as a slang term meaning down and out, or poor and exhausted. The word first came to the attention of Kerouac via a speech given by Times Square hustler-poet Herbert Huncke, “Exhausted, at the bottom of the world, looking up or out, wide-eyed, perceptive, rejected by society, streetwise, on your own.”[2] Rapacious reader of all things Beat back in my high school and college years, I’m tempted to make an addition to the definition. However, Lucien Car’s two cents are worth decidedly more than mine, “It [Beat] was practically impossible to define. Maybe it was a term we just sold ourselves. It was trying to look at the world in a new light that gave it some meaning. Trying to find values…that were valid.”[3] It was this search that drove the Beats to experiment with drugs, sex, music, art, and writing that lead directly to Kerouac’s groundbreaking writing style and the voice waxing lyrical throughout his writing.


Disclosure: In the spirit of the Beats, I decided to write the rest of this article while listening to the jazz Kerouac enshrined from his travels in the pages of On the Road. Specifically, I entered the name of each musician mentioned in the book into my iTunes search and immersed myself in jazz while thumbing my way through the novel again. In the back of my mind, I think the Beats would approve – even dig it – since this is the very type of silly quasi-scientific experiment they’d go for…will the jazz music of the Beat Generation influence my writing as much as it propelled Kerouac and crew from city to city? Or should I play the odds and dig on the jazz while downing cheap whiskey, smoking cigarette after cigarette in a misguided attempt at “method reviewing?”

Obviously, yes.

Stan Goetz kicked off with The Girl from Ipanema as she went walking down the white sandy beach beside an ocean of ancient memories and coquettishly kept secrets. My heart sensed the sad, breezy wrongness of the song for the book: too mellow, too sexy for what I had in mind. I searched out Charlie Parker and found an album he created with Dizzie Gillespie. “Leap Frog Take 5” from Bird and Diz. Now, THIS is the jazz soundtrack of a generation keen on adventure and getting all the kicks life had to offer! Now it was my blaring soundtrack to Kerouac’s On the Road. Kerouac was a whiskey man, but since whiskey makes me mean, I mix an extra dry, slightly dirty vodka martini with feta olives and I picked up On the Road for the first time in over thirty years…


The first time I read On the Road, it was at the behest of my father. He was a high school English teacher who sometimes chose to communicate via the literary masters. I was restless from a very young age. In hindsight, I imagine he wanted to show me what Hilary Holladay of the University of Massachusetts Lowell noted about Jack Kerouac the man. “He was this deep, lonely, melancholy man. And if you read the book closely, you see that the sense of loss and sorrow swelling on every page.”[4], In other words, he wasn’t as happy-go-lucky as you think. Do not attempt to follow in his filthy hobo footsteps. I elected to take my father’s message more literally: move out.[5] Or, maybe the muse of the American road put it more succinctly (if less frenetically) when protagonist Neal Cassady says, “The road must eventually lead to the whole world.” And, man, did I want to see the world. Not just see it, but really follow my lust for life and freedom and sink my teeth into the experiences life’s rich pageant proffered. I wanted to wallow in prose I could admire and, humiliating truth be told, emulate in an unpublished novel or two. Like Kerouac, I was “crazed with my own independence”[6] and left home at seventeen to experience everything life had to offer before it was too late. Time couldn’t move fast enough for me.

Kerouac traversed America via thumb, Greyhound bus, and various models of now vintage American cars. In On the Road, he adventures around the country three times, pausing for various lengths of time in Denver, New York, San Francisco, Laredo, and Mexico City. In wide-eyed, enthusiastic search for wisdom, Kerouac makes it his mission to personally experience every individual, every town, and every oddity in between that caught his eye; he empathetically shared stories of the alienated and others invisible to the progress of so-called great society; he gives tenor to the Beat Generation’s version of the call of the wild.


Go out and drink up life every which way you can.

It’s that siren that kept me up nights as a kid, fed my insomnia through college, and drove me wild on the inside, searching for something intangible but still very real about myself. There was a far bigger world beyond the Detroit suburb where I lived; beyond what I had experienced, read, or witnessed on late-night Cinemax. This world wasn’t one that could be experienced vicariously. I was overwhelmed by the sheer vastness of the experiences still ahead of me in life and I was chomping at the bit to hit the highway. I’m sure Kerouac would have sympathized, “I was a young writer and I wanted to take off…. a writer needs new experiences…and my life hanging around campus had reached completion of its cycle and was stultified.”[7]

Meanwhile, the post-college generic white suburban middle-class life was staring me down. The more plans I made for life after graduation, the worse my wanderlust grew. Ahead of me were countless nights driving through dawn to exotic destinations like Atlanta, Denver, New Orleans, California, Alaska, and New York…experience awaited me. Cheers, I refill my martini glass.

How Kerouac Wrote On The Road Urban literary legend has Kerouac authoring On the Road on a Benderizine-fueled creative jag in three weeks on a single piece of typing paper that he taped together into one looong scroll. He would later use rolls of teletype paper, as he explained on The Steve Allen Show.[8] Truth be told: it took Kerouac an additional four years to work his novel into publishing shape for its 1957 release.[9] Upon learning this, I decided that my own writing process was much too slow. I had a laptop and access to coffee. This kid wouldn’t be banging out a manuscript scroll on an antique Underwood while mainlining amphetamines. Well, I would be pounding the espresso as a Benzedrine substitute.


Kerouac, Neal Cassidy, Allen Ginsberg

Also Under Kerouac’s Influence I was far from the first restless, creative soul to be influenced by Kerouac and On the Road. For starters, there were the other members of the (truly very small and exclusive) Beat Generation – many of whom are also featured in the novel under assorted nom de guerre. Famously mad protest poet Allen Ginsberg appears numerous times as Carlo Marx. Poet and playwright Alan Ansen roll with the handle, Rollo Greb. Notorious writer and prodigious heroin addict William S. Burrough appears as Old Bull Lee. The inspiration for the novel and so many other Beat artworks…the irrepressible force of nature – or human twitch, depending on your POV – was Neal Cassady as Dean Moriarty.

Artists, writers, musicians, and photographers of consequence later acknowledged the importance of Kerouac’s novel in a 2007 article in The Guardian.[10] ‘It changed my life like it changed everyone else’s,’ Bob Dylan would say many years later. Tom Waits, too, acknowledged its influence, going so far as referring to Kerouac and Cassady in a song and calling the Beats “father figures.” Two American photographers (that we know of) also fell under Kerouac’s spell: Robert Frank, who became his close friend—Kerouac wrote the introduction to Frank’s book, The Americans—and Stephen Shore, who set out on an American road trip in the 1970s using Kerouac’s book as a guide. The coming-of-age road trip novel debuted when On the Road was published, opening the playing field up for authors like Hunter S. Thompson to write books like Fear and Loathing in Las Vegas. Not to mention film classics like Fandango[11], Easy Rider, The Motorcycle Diaries, The Blues Brothers, Midnight Run, Thelma & Louise, and – if you think about it – even Dumb and Dumber!

Something changes within you after reading On the Road for the first time. Speaking for myself, between the novel and my friends at the time, I realized that I wasn’t bound to the grand scheme for “future Drew:” attend college (not a clown college, either), start a career (anything legal and realistic that isn’t artistic, fun or involving guns), marriage (no problem as gold diggers found me worthless and, therefore, distasteful as turned oysters), children (all of whom smell terrible), retirement (a writer never retires), then death (writers created the superpower of resurrection). With any luck, I’d be able to choose the date, time means of death, and has veto power over the funeral guest list. The formula for staying middle class seemed pretty simple and all I had to do was walk the line. But as I mention in the headline: I was under the influence of Kerouac (among other many, many other things). Therefore, my journey would be a labyrinthine hedgerow to map.

Story Note: Kerouac writes On the Road in the first-person voice as Sal Paradise. However, once you’ve read more than one book involving both Kerouac and Cassady, you realize they are inseparable from their characters. Moving forward, I’ll be simplifying things and refer to Paradise as Kerouac and Dean Moriarty as Neal Cassady. Don’t like it? Take it up with the Beats.




John Leland, author of Why Kerouac Matters: The Lessons of On the Road (They’re Not What You Think), provides a passable preamble, “We’re no longer shocked by the sex and drugs. The slang is passé and at times corny. Some of the racial sentimentality is appalling,” but adds “The tale of passionate friendship and the search for revelation are timeless. These are as elusive and precious in our time as in Sal’s [Kerouac’s] and will be when our grandchildren celebrate the book’s hundredth anniversary.”[12]

On the Road tells the story of Jack Kerouac, who is at once the narrator and the character upon whom Neal Cassady wields the most influence. Kerouac longs to be a writer of insight and consequence. He’s drawn to people passionate about anything and everything (but everything was best); enthralled by nearly every woman he passes on the street (or sits beside on a bus) but has only the briefest of moral qualms when it comes to making time with one of Neal’s many girls; and, ultimately, he knows just enough about life to understand that the dice are loaded, the system doesn’t tolerate outliers like blacks and intellectuals and America’s endless sadness is implicit. Kerouac meets his future muse and human analeptic Neal Cassady and is “Humbled by Cassady’s mad wit and frenzied lifestyle – he longs to be a novelist and settles in to listen to the artsy-types debate.”[13] Tribed up with fellow Beat travelers, Kerouac and Cassady get their kicks up and down Route 66 (and many of the other highways national and international too) as they crisscross the country in cars large enough to seat four adults up front.

Every stop is an adventure – even if it’s just for gas. Every mile a fresh glimpse of the great American continent. Every hitchhiker they pick up has a story to tell, just as when Kerouac hitches solo, he shares his own story. Within the pages of his novel, Kerouac encapsulates the collective experiences and wisdom of the drivers who pick him up and finds knowledge of the road behind every crooked eyebrow, twitching crow’s foot, and raised thumb.

Hitchhiking In the forties and fifties, hitchhiking was still considered a reasonably safe way to travel on the cheap. The gas, grass, or ass legislation was years from inception and stigma had yet to attach to the colloquial aimless drifter. From servicemen to salesmen to long-distance truckers and star-crossed lovers-on-a-cross-country mission, there was always someone with wheels looking for company and someone who burned to be taken away from here – anywhere else would do. Kerouac realized this convenient and temporary yin yang of the American road and reveled in its naked freedom every time he thumbed a ride. But as both actor and observer, he still has the sense to tell the hustlers from the murderers from the perennially-down-on-their-luck poets. This is not a sixth sense to be taken lightly. Neal Cassady does not possess this superpower and thinks the world is as honest as the day is long. Running on fumes and out of dough, Neal and company pick up a hitchhiker on their way to Denver who “promised them a dollar if they let him ride to Memphis. In Memphis he went into his house, puttered around looking for the dollar, got drunk and said he couldn’t find it.”[14] Later, despite the legend of having been literally born on the road and having an unaccountable hobo for a father, Cassady suggests that perhaps the best-case scenario for the two men [Kerouac and Cassady] would be to live out their days as hobos. “’ Why not, man? Of course, we will if we want to, and all that. There’s no harm ending that way. You spend a whole life with the non-interference of the life of others, including politicians and the rich, and nobody bothers with you and cut along and make it your own way.”[15] There were no limits to the possibility life had to offer within the cosmology of Cassady – except the tedious ones imposed upon him like time, money, work, marriage, kids and the rest of eternity decomposing six feet under. Kerouac rebelled against those constraints himself and loved Cassady for his innocent outlook and yearning to squeeze the world for all its marrow, for blazing a different trail through the glittering and vast American wilderness.

Anchorage, Alaska By the close of the twentieth century, which was when I hit the road and did a bit of hitchhiking myself, the activity was verboten in all forty-eight of the contiguous United States. In Alaska, however, the spirit of the frontier (and sympathy for people traveling by thumb) remained alive and well. The risk of picking up a backpacking stranger was considerably less than being attacked by bears, wolves, moose, or wild dogs on your morning constitutional. (I would experience each of the aforementioned majestic animals on separate occasions, only one of which was an attack, and – admittedly – it was totally my fault for leaving the food out that attracted the family of bears.) My virgin hitchhiking launch point was just beyond the Anchorage airport on the AK-1 heading south. Even all those years ago, May was unseasonably warm. Climate change reared its Kraken-sized head in the far north way earlier than the rest of the planet. Nevertheless, as a guy who prefers – and expected colder temperatures – the heat was as unwelcome as the squad of giant mosquitoes patrolling the local air space. After waiting for several hours on the side of the highway, alternating my hitching arms as each grew tired, my clothes clung to my body, tacky with sweat. It didn’t take long for despair to overcome me. No one in their right mind would pick me up. My luggage was an Army Surplus duffel that weighed nearly as much as I did. I had long, greasy hair. I didn’t look worth robbing. I just knew that I was going to end up on the menu for the apex predators in the immediate vicinity.

As what passed for dusk in Alaskan May diminished the sunlight and temperature by a shade or two, a yellow Checker cab drove past me, then slowed and pulled over for me. Great, I thought, chagrinned that my first ride wanted to charge me a fare. I approached the yellow Crown Vic anyway. Before I even got close, two men in their late twenties jumped out of the back and asked where I was headed. I was going to Kenai in search of cannery work. Princes among men, these citizens of the world (former US Air Force from Brooklyn) offered to help me reach the peninsula and find work – that was their reason for being there too. I hopped in the cab and two hours later the three of us split a blunt and watched the tide ebb back out to sea from the balcony of a hotel with more antlers on the wall than guest rooms.

The day I landed in Alaska I did something on my bucket list: I saw both the Atlantic and the Pacific oceans within twenty-four hours. I didn’t feel like an explorer or anything so predictably prosaic. Worse, I felt American. Like I could take personal credit for flapped my wings across the North American continent. Like I invented the plane and piloted her myself. Like I had successfully completed the first leg of my trip and should celebrate with beer! Fortunately, my two new friends were both of legal age to purchase alcohol. I was an inexperienced, wet behind-the-ears eighteen-year-old with a shitty fake ID and resting dumb face. The three of us bellied up to the hotel bar where an attractive, college-aged girl dispensed fifty-cent Hamm’s beer (in a can) and nachos bowling alley-style. I didn’t know it then, but that bartender was one of only a handful of women my age that I would see during my entire Alaskan adventure. The population of Alaska was sparse and widely distributed. The numbers were far, far, far from my favor. Accounting for full-time residents, loggers slitting the throats of primordial forests, oil roughnecks working so far in the wilderness it was only accessibly via puddle jumper then helicopter to the thousands of seasonal fishermen and cannery workers, there were maybe twenty women, I guessed. And each could wrap the entire state around her pinkie finger. There was something to be said for being the big fish in a small pond, I supposed. Suffice it to say, I had a girlfriend at home, and, oh yeah, I was a one-hundred-pound weakling unlikely to survive a toe-to-toe tussle with any of the enormous loggers and fishermen at the bar, each of whom was exactly one foot taller than you’d imagine. I kept my head down and thanked the young lady for my Hamms.

Now feels like the perfect time to mix up things. Search out Perez Prado on your iTunes. Select Skokiaan and dig that teasing sax. Switching to beer now: a pint of Bell’s Two-Hearted Ale to be exact. The first one goes down too easily.

America Kerouac was raised in a French-speaking home in Lowell, Massachusetts, and did not speak English until age six. During World War II he served as a merchant marine. Whatever his reasons, Kerouac felt that it meant something to be an American. He puts his finger on it numerous times and then shrugs off any attempt at the definition as decidedly un-American. Throughout On the Road, he references America and treats the subject as he might a stepsibling, one he loves dearly but struggles to understand. Occasionally, he clues in the reader to what he’s thinking but more often he’s prone to a larger metaphor of America. He described the country using adjectives synonymous with insanity, incongruity, and experimentations in excesses of all kinds – yet these sentences and ideas still leave conceptual America up to your imagination. “I felt like a million dollars. I was adventuring in the crazy American night.”[16] America is, at once, wild, mad, crazy, insane, mythic, epic, poor, sad, salacious, lyrical, merciless and somehow, some days, moral. In the end, that left Kerouac, “as lonely as America.”[17] Like the country itself, everyone within its borders was in a constant state of flux. Both Kerouac and Cassady found continuity in change as American a phenomenon as jazz and moonshine. Traveling “over a hill overlooking Salt Lake City…when he [Cassady] opened his eyes to the place in this spectral world where he was born, unnamed, and bedraggled, years ago. ‘Sal [Jack], Sal, look. People change, they eat meals year after year and change with everyone!’ He was so excited that he made me cry.”[18] This is Kerouac lamenting the loss of his own wide-eyed innocence, but as he learns on numerous occasions in On the Road, you can never really go home again. (A lesson he might have learned from Thomas Wolfe, who was one of Kerouac’s favorite authors.) Cassady’s birth into transience and his innocuous, optimistic outlook on the future were tragic to Kerouac, but still something he envied in his friend. Something held him back. Something stopped Kerouac from discovering whatever it was he searched for so earnestly in his writing. Denver Following Giants in the Foothills


Denver, Colorado – still very much a cow town at the time of Neal Cassidy’s birth – was also a sketchy locale full of sketchy characters, where outsiders like the Beats were tolerated even as they carried out their social and creative experiments. Denver: one of my favorite cities in the world, home of my college alma mater. Neal Cassady called this city home and it was to Denver that Kerouac and company return sporadically both for adventure and honest paying work. Denver – where the treed foothills fuzzy with tumbleweeds and suburban sprawl extended their reach to the front range of the glorious Rocky Mountains. Carlo Marx writes poetry and experiments with drugs and sex from a basement apartment in a red brick building off Grant Street. I walked Denver’s Capitol Hill neighborhood from my apartment on Washington Street to class for years, always wondering if a certain house was his, or if he’d stayed at a different, pre-war house with a visible basement apartment. I’m sure it’s long razed by now. There was, however, one tourist destination on my Capitol Hill commute: the mansion of Molly Brown, otherwise known as “the Unsinkable” Molly Brown after she survived the Titanic. Little known MB fact: she was the first woman to run for US Senate – eight years before women had won suffrage.

Another Denver/Kerouac connection: there’s a bar just up the street from where I worked downtown after college. In Kerouac’s day, it went by Paul’s Place. Today, we affectionally know it as “My Brother’s Bar.” On the wall is a letter, a carryover from the décor of Paul’s day that couldn’t be 86-ed, “A familiar literary artifact linking today’s cold pint on a warm afternoon with the infamous summer of 1947, when Kerouac fled New York for San Francisco, by way of Denver with a larger-than-life cowboy [with an unpaid bar tab] named Neal Cassady.”[19] I’ve been to My Brother’s Bar more times than I can count and have very few recollections of leaving. Going there, however, usually involved a who’s on first, sort of Mobius conversation that only I found funny:

Someone would suggest that we go to My Brother’s Bar late at night. I would say, “Right on, your brother owns a bar?” The person suggesting shots for last call shoots me a withering glare. As if I had deliberately misunderstood. “No,” They capitulated at least once (everyone did), “The name of the bar is My Brother’s Bar.” I say, “Cool, what’s it called?” Much as it amused me, I’m sure this is precisely the sort of convo edited out of On the Road, reworked with the help of much coffee, Benzedrine, and morning’s sobering light. Probably an editor or two, too. My Brother’s Bar, Denver From the eighth floor of the advertising agency that employed me to write quasi-pithy television commercial scripts for a Big Three Detroit automaker, we had a three-hundred-and-sixty-degree panoramic view of Denver.


From the conference room, we could catch the sunset in late August when, after it rains for ten minutes around three pm (you can set your watch by it), the Rockies would brood black against the explosion of atomic red and orange photons of infinite hues. I could see Larimer and Market Streets in lower downtown, which were a known skid row in Beat times. Today, hip-seeming people frequent the area and call it LoDo, which includes an endless number of identical bars (same bar, same menu, same– cloned? – clientele).

I could see my school: the University of Colorado at Denver and the tower of the Tivoli building – formerly a brewery, my college bar, and last time I visited, a museum of a brewery where alcohol wasn’t permitted); the old Mile High Stadium – currently and awkwardly named Empower Field at Mile High. Just north of the office building the Union Station sign glowed neon night and day, welcoming newcomers to the city in Beaux-Art style. This would have been where Kerouac and crew entered the city if they came by train – either via ticket or hopping a freight car. I imagined they showed up dehydrated, still loaded to the gills on Old Grand-Dad bourbon, stinking of stale cigarette and pot smoke, and staggering out of rusty metal boxcars like old-school hobos, but with slightly more ambition (booze, jazz, and fucking). Today, the redeveloped Union Station includes a hotel and numerous restaurants and bars. Where have all the philosophizing, “hip flask slingin’ madmen”[20] gone?

Hey Jack Kerouac Snagging another Two-Hearted Ale. On the iTunes? You guessed it: Hey Jack Kerouac by the band 10,000 Maniacs.

Natalie Merchant’s lyrics sum up how Kerouac found wisdom and inspiration to write and what made him powerful:

Who [Kerouac] chose his words from mouths of babes, got lost in the wood. Hip flask slinging madman, steaming cafe flirts. They all spoke through you.[21]

He found his wisdom on the road, on the journey, as it were. It wasn’t sourced from The Bible, The Torah, The Koran, an intro to philosophy textbook, or even his fellow Beats. Kerouac philosophizes for the little guy in all his permutations and plights; for life’s well-intentioned down-and-outs and conspicuous reprobates; for people who just want to be left alone and for people who wanted to change the world. From the naïve perspective of a white college kid, hitting the highway and finding some street wisdom of my own sounded like a much more pleasurable path to the truth than reading another round of the Greek philosophers. After all the adventure books I’ve read since I was a kid, On the Road was the only book that made it seem possible, realistic even to hit the road on my lonesome to find America and myself. Kerouac offered an alternative vision at a critical moment in my life. Perhaps the only voice I heard louder was Ferris Bueller saying, “You can never go too far.” And that’s exactly where I would head next, chasing the ephemeral “On and on into the American night.”[22]

  1. https://slate.com/culture/2001/03/hey-jack-kerouac.html ↑

  2. The Portable Beat Reader, Ann Chalmers, The Viking Portable Library, p. xviii ↑

  3. Ibid, ↑

  4. https://www.inquirer.com/philly/entertainment/literature/20070826_The_one_less_traveled_by_Readers_head_down_Jack_Kerouacs__quot_Road_quot__again_as_the_book_turns_50__propelled_by_the_jazzy_go-go_spirit__perhaps_repelled_by_the_immaturity_and_datedness_.html ↑

  5. This was the opposite of his intended message to me. ↑

  6. Kerouac’s Introduction to “On the Road” from the Quality Paperback Book Club ↑

  7. Biography from the inside cover of “On the Road, The Dharma Bums and The Subterraneans” from the Quality Paperback Book Club p. 9-10 ↑

  8. What Happened to Kerouac, Richard Lerner, 1986 ↑

  9. Ibid p. 24 ↑

  10. https://www.theguardian.com/us ↑

  11. If you haven’t seen Fandango, give it a chance. Kevin Costner’s made some bad movies, but this is definitely not one of them! ↑

  12. Leland, John (2007). Amazon.com: Why Kerouac Matters: The Lessons of On the Road (They’re Not What You Think) – Questions for John Leland. ↑

  13. Biography from the inside cover of “On the Road, The Dharma Bums and The Subterraneans” from the Quality Paperback Book Club p. 24 ↑

  14. On the Road, The Dharma Bums and The Subterraneans” from the Quality Paperback Book Clubp.80 ↑

  15. Ibid, p.251 ↑

  16. Ibid. p.100 ↑

  17. Ibid. p.240 ↑

  18. Ibid p. 211 ↑

  19. https://www.denverpost.com/2010/06/25/walk-in-the-footsteps-of-colorado-writing-giants/ ↑

  20. 10,000 Maniacs, In My Tribe, “Hey Jack Kerouac,” Lyrics by Natalie Merchant, 1987 ↑

  21. Ibid. ↑

  22. On the Road, The Dharma Bums and The Subterranean” from the Quality Paperback Book Club, final sentence. ↑


Drew Bufalinihttp://www.drewbufalini.comAndrew “Drew” Bufalini is a freelance writer and user experience designer. He has worked in advertising, software development, healthcare marketing, social media, and content strategy. He has a B.A. in English from the University of Colorado and certificates in User Experience Design from Google and Content Strategy from Northwestern University. He lives in Michigan with his wife and new puppy.

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