The magnificent song that took Bob Dylan “10 years to live and two years to write”

Pick up a modern copy of Jack Kerouac’s On The Road, and you will find in the inside sleeve a testimony from Bob Dylan stating, “It changed my life like it changed everyone else’s.”

The romantic hysteria that the novel induced was partly to do with the notion of Kerouac himself. Here was a man who hadn’t slaved over a desk in some studious, dusty office. He had gone out there and lived it all for real, caught culture on the wing, raced back and transposed everything in prose with the sort of expressionist wonder that only experience can reap.

Now, the beats were determined to do the same: To grab culture by the lapels, shake it like a flatpack wardrobe in a hurricane, and send it a decree saying the times are changing and “Your old road is rapidly agin’ / Please get out of the new one / If you can’t lend your hand.” Those words, much like Kerouac’s novel, offered up the same sense of creative revolution—artists would now roll up their sleeves and illuminate society like a showbiz for the wider populace to purvey. Hence, the phrase pop culture. Everything was moving forward at a pace, and it was high tide art joined it. 

Thus, Jack Kerouac got busy being busy, and then he distilled his findings in a frenzy. As Steve Allen famously asked Kerouac, “Jack, I’ve got a couple of square questions, but I think the answers will be interesting: How long did it take you to write On The Road?” To which the ever-taciturn Kerouac replies, “Three weeks.” With surprise, Allen follows up, “Gee that’s amazing, how long were you on the road itself?” And once more, in the matter-of-fact manner of an innocent man in a police interview, Kerouac says without reproach, “Seven years.”

Allen’s punchline is: “Once I was on the road for three weeks and it took me seven years to write about it.” Kerouac doesn’t laugh. This exchange seemingly was not lost on Dylan, and the famous magpie who takes from here, there and everyone used a similar account when describing his epic track ‘Tangled Up in Blue’. “It took me ten years to live,” he said, “and two years to write.”

Bob Dylan - 1966 - Musician
Credit: Far Out / Alamy

The similarity between that phrase and the one Kerouac often touted is no coincidence. Dylan is a master thief. However, as Nick Cave explains, theft is an engine of cultural progress: “The great beauty of contemporary music, and what gives it its edge and vitality, is its devil-may-care attitude toward appropriation — everybody is grabbing stuff from everybody else, all the time. It’s a feeding frenzy of borrowed ideas that goes toward the advancement of rock music — the great artistic experiment of our era.”

This wasn’t lost on Dylan. Rock ‘n’ roll was the great mixing bowl that Kerouac had first brought to the boil. Literature for the first time had lost its artistic paramountcy to something new and exciting that could capture culture and serve it up far faster than even Kerouac’s blood-splattered typewriter. Dylan found himself on the precipice of new artistry, with a history of art sprawled out behind him, and nothing ahead, as is ever so on the road to new cultural horizons. 

A part of arguably Dylan’s greatest album, Blood on the Tracks, ‘Tangled Up In Blue’ represents one of Dylan’s most enterprising moments, all the while maintaining his notorious drawl. Though the singer had always been open about his feelings, allowing his music to do most of the diarising needed to succeed in the pop world, this track is one of his most open.

Not because it accurately depicts the ending of a doomed relationship, though it does that with the sweetest efficiency, but because he portrays them in a veracious and voicefrous way, through fragmented vignettes. The kind that usually only arrives after the event, but for Dylan’s artistic eye, appeared within a moment’s notice. It provides grounding to one of the singer’s finest efforts. 

What does ‘Tangled Up In Blue’ mean to Dylan’s legacy?

In this sense, ‘Tangled Up in Blue’ is almost his definitive anthem. While it might seem like a personal corroboration on the surface, it is dripping with a spiritual sense of timelessness. As Dylan explains himself: “It didn’t pertain to me. It was just a concept of putting in images that defy time – yesterday, today and tomorrow. I wanted to make them all connect in some kind of a strange way.”

All of that takes a lot of consideration and ‘Tangled Up in Blue’ is as layered as the Earth’s crust. Brooklyn location names like Montague Street, hint at the last name of Shakespeare’s Romeo in a great act of literary foreshadowing. And then he floods in the contemporary references to The Beatles with nods to their songs like the shoehorned ‘From Me to You’, and later he sings in the same shifted key, ‘Revolution’. 

In short, the song is an amble through time and culture. And Dylan arrives at this timeless motif in a perfunctory sense as he cries, “But me, I’m still on the road.” And he always will be, it’s the very point of his artistry. He’s literally still on the road even at 81. As he told Pete Townshend: “I asked Bob Dylan why he does so many gigs. He told me, ‘I’m a folk singer. A folk singer is only as good as his memory, and my memory is going.’ He’s doing it to keep his memory alive.”

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