John Leland, like many readers, first cracked a copy of “On the Road” in his late teens. He remembers the rush of it, “feeling that excitement that’s something like when you hear The Rolling Stones for the first time.” Then, as with many readers who read the book when they’re young, it receded into the distance of his life. A few years ago, however, as Leland researched his book Hip: The History, he returned to “On the Road” and found an entirely different tome awaiting him, one with real lessons about love and sex and art and God.

That experience led to Leland’s new book, Why Kerouac Matters: The Lessons of On the Road (They’re Not What You Think), a smart, insightful and playful exploration of the novel. He spoke to me by phone from New York, where he works as a reporter for the New York Times.

World Hum: What do most people think are the lessons of “On the Road”?

John Leland: Well, I think that Dean Moriarty is one of the most captivating and compelling characters in American literature. Most of us read the book when we’re young—I read it at 18 or 19, and I suspect that you did as well.

I did.

And we’re just captivated by that character. We want to follow him out on the road, and throw down what we’re doing and go out in search of kicks and chicks and bombing around the country because he does. And I think that is a huge, huge part of “On the Road.”

But within the book are other stories. Any good book contains a number of narratives, and there’s Sal’s story. He really outgrows Dean and puts some distance between the two of them. He starts off just as we do, utterly captivated by this Moriarty character. And then over the course of the book Sal goes from being an apprentice to really being the older character. And I think a more in charge figure. So there are lessons about growing up and making your way in the world, lessons about work and money and love and sex and family.

We recently put together a list of the 10 Greatest Fictional Travelers, and we picked Sal as our top character. We didn’t have Dean represented. I’m curious what you think about where Sal fits in with great fictional travelers.

Was he up there with Odysseus, Ishmael and Huck and Jim?

Odysseus was No. 3, and Huck and Jim were No. 7. Ismael didn’t make our cut. We had to cut many contenders. Sal fits there, though, as a more complex character than Dean.

Well, Dean is the guide we all want on the road with us and Sal maybe is the traveler we’d all like to be. We expect travel to change us in some way or to help us grow in some way. And for Sal it does that.

What do you say to people who just want to read “On the Road” for the kicks and adventure?

I say enjoy the book for the kicks and adventure. I don’t want to do anything to distract them from that. But there’s another book in there as well. You can enjoy that. The diamond twists and you can enjoy the light refracting through it in different directions. But there is more to it than just that ode to irresponsibility, which I don’t think was Kerouac’s intention.

You write in “Why Kerouac Matters” that Kerouac “had always been a conservative—a blue collar son, Catholic, a veteran of the merchant marine and (briefly) the navy.” You add that he lived a life at odds with those values. Are there any lessons we can take from Kerouac himself?

Well, that gets a little harder doesn’t it?

The one thing about Kerouac that gets missed is that he didn’t have these adventures and then somehow accidentally the novels popped out. He had a tremendous work ethic that took its toll on him. The idea that you would turn out novel after novel in the face of rejection, I think there’s an admirable, almost heroic quality to that. I don’t know that I would have the wherewithal to do that.

He really believed in his writing and he believed in art and he was willing to make sacrifices for that and to distinguish between work that mattered, authentic work, and things we do just to be able to buy more stuff.

The work obviously does matter. It’s endured for 50 years. We’re celebrating it now. Why do you think it endures?

I think some of the lessons in the book are timeless and that involves both Dean and Sal. That desire for ultimate freedom, and the kind of manly ultimate freedom that Dean embodies. I think that’s timeless.

Then I think the spiritual quest that Sal is on, that’s timeless as well. That search to a) know yourself and to know who you’re going to be in the world, and b) the search for a higher power that Kerouac said was the heart of the book. I think that’s timeless as well.

Do you have any favorite parts or any lessons you personally take from it?

I think the funniest line in the book—there’s great humor in it—is when Dean says to Sal, “I’ve always dug your feelings, and now in fact you’re ready to hook up with a real great girl if you can only find her and cultivate her and make her mind your soul as I have tried so hard with these damned women of mine. Shit! shit! shit!”

The book still has some mysteries for me. There are some passages I can’t make sense of. There’s a lovely line when he’s hitchhiking with the girl Terry, that he meets in Bakersfield outside L.A. and they’re migrant farmworkers together. And he says something that I think is a typo: “Who did they think they were, making fun of a girl reduced to poor circumstances with a man who wanted to belove?” Belove is one word there. I thought that was a beautiful line.

But the whole trip to Mexico is just the best part of the book. I think Kerouac was really learning to write as he went along, and there’s a richness to the images and the juxtaposition of the religious vision and the pot and the whorehouse. And mambo—all those things put together in the space of 10-15 really dense, rich pages. I look forward to it whenever I get to that part.

How many times have you read “On the Road” now?

I don’t know. During the course of writing the book I’d read it every couple of weeks.

You write a bit about the mythology that has evolved around the book. There’s an aside where you mention that some of the things popularly associated with “On the Road” and the Beats—goatees, espresso bars, Levi’s—had nothing to do with Kerouac or the book. Why did that mythology evolve?

Those of us who weren’t there at the time, we read the book though the filter of the ‘60s counterculture, I think. One of the things that I wanted to do in my book is excavate it from that post-’60s perspective. Kerouac didn’t write it to create the ‘60s, although people often say that. But I think that is a distorting prism. And I don’t mean that I’m a ‘60s person, because I’m not. I’m condemned to be a ‘70s person. But I think that reading it post 1960s, post Woodstock and the counterculture, I think that that becomes a framing for it.

Thanks, John.

Michael Yessis is the co-editor of World Hum.