20 Reasons to Read “On the Road” in Your 20s

14 Aug


It recently came to my attention that Buzzfeed posted an article called “65 Books You Need to Read In Your 20s,” and I immediately knew Jack Kerouac would make the cut. After all, so many people have told me Kerouac is for young people.

First, though, at number 18 came Ernest Hemingway’s The Sun Also Rises. The write up states:

Another English syllabus special, Hemingway’s tight prose and peerless storytelling are somehow more resonant when you are reading it on your own. Or as my colleague Matt put it: “I couldn’t keep my eyes open for more than five pages of Hemingway growing up, but for some reason I picked this up in my post-graduation haze and was mesmerized.”

I can see that. I was none too fond of Hemingway when I had to read The Snows of Kilimanjaro in class but post-grad enjoyed The Sun Also Rises. It’s been quite some time since I’ve read it and have been thinking I should reread it.


So what do we hear when we get to Kerouac, at number 34? A solitary, cynical line:


So that you’ll realize the way you felt about this book in high school has totally changed.


Really? Kerouac made the list just so that the blogger could diss On the Road? I’m all for personal growth and maturity, and I can certainly understand how some books are more relatable when you’re young, but, even if one thinks that’s the case with On the Road, why suggest someone “waste” valuable reading time rereading it then? Furthermore, why single out On the Road and not, say, Catcher in the Rye? And, if On the Road is deemed a book for teenagers, what are we to make of all the legions of adults who read Harry Potter?


I first read On the Road when I was a teenager, and I read it again when I was in my twenties. And guess what? I continue to pick it up and find inspiration from it. In fact, I think I appreciate certain aspects of it more now than I did when I read it in my teens. Therefore, I’d like to propose reasons why you should read On the Road in your twenties:

  1. Jack Kerouac who? You were busy with homework, video games, and the mall, and never read anything but assigned reading—which never included Jack Kerouac. That’s okay, you can read On the Road now.
  2. You understand more about history and politics now that you’re older and consequently can better understand the significance of this novel being written by an author who served in the Merchant Marine during World War II.
  3. You had heard about the Great Depression, but you didn’t know back then how that was tied to literary movements, and now you can see how money has shaped the art from The Great Gatsby to The Grapes of Wrath to On the Road.
  4. Much of contemporary literature uses a conversational voice so it never occurred to you that Jack Kerouac’s voice, diction, and stream of consciousness were revolutionary for his time period.
  5. You’ve delved into Allen Ginsberg, William S. Burroughs, Gregory Corso, amongst others, and now can make your own judgment about whether or not the term “The Beat Generation” is useful and appropriate.
  6. The main characters in On the Road are in their twenties. The struggles they face growing up and becoming mature adults are the same ones you now face.
  7. You weren’t allowed to take a bus across the country when you were a teenager. But now you can!
  8. You lived a quiet life in the suburbs as a teenager and weren’t exposed to people who’d been in jail, habitually did drugs, married and divorced, and didn’t hold down steady jobs as adults. Those characters may feel less foreign to you as you get older, and you may see them differently now.
  9. When you read the novel as a teenager, you thought Dean Moriarty was the hero. You’re not so sure anymore. This makes Kerouac’s portrayal of him even more intriguing.
  10. You skipped past all those setting descriptions, but now you realize they are pure poetry.
  11. The frenetic travels in the novel seemed exhilarating but confusing or pointless the first time you read the novel. Now, you can examine that as an intentional plot device.
  12. You didn’t think much of the religious aspects of the novel, but now, having heard more about Kerouac’s Catholicism and Buddhism, you can’t help but analyze their significance. This could change your perception.
  13. You enjoyed the romance of “the Mexican girl,” but you didn’t think too much about Kerouac’s portrayal of Mexican and Mexican American field workers, and now you can draw parallels to today’s discussions on the treatment of certain ethnic groups in America.
  14. You want to learn how to write better dialogue.
  15. You read the characters through a contemporary lens when you were younger, but now that you know more about the 1940s and ‘50s you have a greater understanding of the social norms of the time and how they relate to masculinity and gender roles. This can allow you to reexamine issues of identity, misogyny, and power in a novel that includes heterosexuals, bisexuals, homosexuals, male leads, and female minor characters.
  16. You realize in many ways the novel is a love story of America.
  17. You have actually listened to jazz by your twenties and read a little about music theory and now understand its role in the novel and its influence on Kerouac’s prose stylings.
  18. Cars have always been a part of your life, but now that more people your age are eschewing driving, you have a greater appreciation for the socio-economic dynamics of car culture.
  19. You realize that maybe in your younger years you were a bit of a follower, like Sal Paradise, and are now seizing the moment and establishing your own life.
  20. You want to learn how to experiment with syntax.

What would you add to this list?


6 Responses to “20 Reasons to Read “On the Road” in Your 20s”

  1. jackiemania August 14, 2013 at 8:41 am #

    Whenever someone makes a comment like such about On the Road, I can’t help but think they only saw what they wanted to in it (whatever age they read it at). How can so many people miss the deep vein of sadness that runs through the book? I would think Kerouac would agree. As he wrote in Desolation Angels:

    “And just like in New York or Frisco or anywhere there they are all hunching around marijuana smoke, talking, the cool girls with long thin legs in slacks, the men with goatees, all an enormous drag after all and at the time (1957) not even started yet officially with the name of “Beat Generation.” To think that I had so much to do with it, too, in fact at that very moment the manuscript of Road was being lineotyped for imminent publication and I was already sick of the whole subject. Nothing can be more dreary than “coolness” (not Irwin’s cool, or Bull’s or Simon’s, which is a natural quietness) but postured, actually secretly rigid coolness that covers up the fact that the character is unable to convey anything of force or interest, a kind of sociological coolness soon to become a fad up into the mass of middleclass youth for awhile. There’s even a kind of insultingness, probably unintentional, like when I said to the Paris girl just fresh she said from visiting a Persian Shah for Tiger hunt “Did you actually shoot the tiger yourself?” she gave me a cold look as tho I’d just tried to kiss her at the window of a Drama School. Or tried to trip the Huntress. Or something. But all I could do was sit on the edge of the bed in despair like Lazarus listening to their awful “likes” and “like you know” and “wow crazy” and “a wig, man” “a real gas”—All this was about to sprout out all over America even down to High School level and be attributed in part to my doing! But Irwin paid no attention to all that and just wanted to know what they were thinking anyway.” (358-359)

    He was so angry/sad that this is what people distilled from his work. Sigh.

    • Stephanie Nikolopoulos August 14, 2013 at 10:02 am #

      Yes, yes, yes! This is a great quote. One that rings true still today with the prevalence of “cat beards,” mustaches on sticks, and chevron.

      You make a good point about age. I referenced age because that particular article was about age but also because so many articles I read on Kerouac suggest that he’s only to be read when you’re a teenager. You’re quite right though that it’s less about age and more about a person’s intelligence and sensitivity. Even when I was a teenager, I felt the melancholy in Kerouac’s writing. So often people reference the “the only people for me are the mad ones” quote, and I love the intensity and passion of the quote, but what really gets me — what got me back then as a shy teenager and what continues to get me today — was the part that precedes it: “…and I shambled after as I’ve been doing all my life after people who interest me….” Here was a guy who wasn’t the “mad one.” Here was a guy who felt left out when Cassady and Ginsberg met. Here was a guy who got ditched by his wild and exciting friend multiple times. Kerouac couldn’t even get hitchhiking right! On his very first big cross-country trip, he couldn’t even successfully hitchhike out of the state and had to return to the city to buy a bus pass. I think Kerouac and his novel have so much myth attached to them that people oftentimes read too much with that in mind and miss out on the very points you make.

  2. J Haeske August 19, 2013 at 12:16 pm #

    Spot on, Stephanie. Don’t know what I would add, but I think the points number 3,8,9 and 17 are especially true.


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    […] And why do Lord of the Rings nerds get a free pass for liking Tolkien well into their adult years while society derides Kerouac as a novel just for teenagers?? […]

  2. Hemingway and Kerouac Explain “Lost” and “Beat” Characters | Stephanie Nikolopoulos - July 23, 2014

    […] 20 Reasons to Read “On the Road” in Your 20s […]

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