Dennis McNally’s roots in American musical culture spread beyond his books Desolate Angel: Jack Kerouac, The Beat Generation & America and A Long Strange Trip: The Inside History of the Grateful Dead. McNally, a historian known for his work as an authorized biographer of the Grateful Dead, was also the band’s publicist from 1984-2004. More recently he’s worked with artists such as Bob Weir and RatDog, Steve Kimock, Bela Fleck, Little Feat, New Riders of the Purple Sage, Boris Garcia, and many others.

And now, his latest book On Highway 61: Music, Race and the Evolution of Cultural Freedom is on its way to public release in October of 2014. I got a chance to talk to Dennis about his new book—I even have an early draft which I can’t share here but I can tell you the final book is under 400 pages with a photo insert. You can read on to get the inside scoop, as well as read excerpts and sign up for news on his website:

AW: If you had to sum up On Highway 61: Music, Race and the Evolution of Cultural Freedom in one sentence, what would it be?

DM: My elevator pitch has been: It’s a book about the long relationship of young, white people and black music, going back from minstrelsy in the 1840s through the 1960s, where you can see it revealed in the music of Bob Dylan.

But more simply: It’s a book about the deepest roots of rock ‘n’ roll.

AW: How is On Highway 61: Music, Race and the Evolution of Cultural Freedom different from your previous books on Jack Kerouac and the Grateful Dead?

DM: Geographically, On Highway 61 is focused on the Midwest of the U.S. In contrast, my first book Desolate Angel focused on the East Coast, while A Long Strange Trip focused on the West Coast.

Chronologically, since I graduated from high school in ’67 and college in ’71 and watched the 60s go down, my books on Kerouac and the Grateful Dead were part of a two-volume history of the post World War II era. On Highway 61 goes back to the roots of the cultural wars of the 60s that many still haven’t gotten over—mostly the “sex, drugs, and rock ‘n’ roll” and the relationship between white people and black music.

Source: Wikipedia

Source: Wikipedia

AW: So, now let’s get literal—how many times have you driven on Highway 61 (aka The Blues Highway)? And what’s the significance for this book?

DM: When I finished writing and editing my book on the Grateful Dead, I went through a sort of postpartum depression and I realized I needed to “stay pregnant” to avoid feeling that way. That’s when I got my idea for this book and I even drove the length of the Mississippi River during this time. I’ve made two complete trips up and down the “River Road” as it’s also known—between Minnesota (near the Canadian border) and Louisiana. But I’ve crossed and driven on it too many times to remember.

The significance of Highway 61 is related to the emancipation of slaves. After slaves were freed, many black people were still bound to the land and sharecropping in the South along the Mississippi River. Highway 61 is the main highway along the river which many traveled and worked upon in the heart of the country. It’s as though the River was a source of energy and power. One generation after slavery, there was an explosion of musical creativity that started with ragtime, then progressed to blues and jazz.

Bob Dylan also has an album titled Highway 61 Revisited and demonstrates a progression of folk to rock—the fusion of black and white music. There was a radio DJ out of Little Rock, AK named “Gatemouth” Page who broadcasted black music after dark—Jimmy Reed, Little Richard, Muddy Waters, Ray Charles—and that music made its way up along the River Road to Bob Dylan who lived at the top of Highway 61 in Minnesota.

AW: Did you have a breakthrough or “AHA!” moment while writing?

DM: It happened when I read Dylan’s book Chronicles. The book confirmed a lot of my theories and focused on Highway 61 the road, but it left me with one question: What about the river?

There’s a story in Chronicles about John Hammond, Bob Dylan’s producer, who gave Bob a record by Robert Johnson called King of the Delta Blues Singers—a record that also blew the minds of music critics like Greil Marcus and Robert Palmer at the time. The was also a lot of counter-criticism about how white people loved Robert Johnson but black people didn’t care at all about him or his music and that the hype around Robert Johnson was just a creation of Rolling Stone.

AW: What material did you use for sources?

DM: 99% of my research was done from reading library books so the material is familiar. However, what nobody has talked about much is the minstrel era from the 1840s. For example, the Fisk Jubilee Singers of which Mark Twain was a fan.  Twain’s book Huckleberry Finn also highlights themes of minstrelsy as well as of white freedom and black freedom—a link to Henry David Thoreau’s philosophical influence in Civil Disobedience and the young, white radical abolitionist mindset of “if they’re not free, then I’m not free.”

In fact, it all starts with Thoreau—I had written almost 150 pages about Thoreau at the beginning of the book, much of which I had to cut down.

AW: Do you have any advice for historians, storytellers, or writers in-training in the digital age?

DM: Keep writing and don’t stop. The main requirement for this type of work is the capacity to endure boredom and to keep going. My first book took me 7 years to write, my second book took almost 20 years, and third book almost 13 years. After finishing my third book, I’ve realized the quality in the capacity for hard work.

The first book I wrote by hand even though I was a fast typer because I wanted to slow myself down. I had to type up my 600-page manuscript three times during the process. My second book had to be typed from handwritten notes in 30, three-ring binders. At that time, my wife had one of the first Macintosh computers and I realized its impact in editing. This third book was also a mixture of adding notes into a computer. I think the entire file is about 1MB and its nice to be able to send it to my editor with one click of a mouse.

AW: What are your touring plans for the book?

DM: There’s a list of upcoming appearances on my website and I’ll be coming to the East Coast traveling between Washington DC and Boston sometime in late-October and early-November.