“I find it full of tragedy and comedy”: The city Bob Dylan felt the most comfortable in

Ever since Bob Dylan packed up his guitar and a handful of clothes, leaving St Louis County, Minnesota, to hitchhike to New York, he was destined to live a rambling life on the road, belonging to nowhere.

The ultimate warrior poet, it was almost as if he was put on earth to spread his artistic message from city to city, eulogising his lyrics that helped contextualise the ever-maddening world we all found ourselves in. 

You could argue that upon his arrival in New York, he found something of a natural home. In the crowded neighbourhood of Greenwich Village, Dylan embraced the folk community that he had only dreamed of through the immortal genius of Woodie Guthrie. There, his fame could flourish in the glamour of the Empire State, which also gave him plenty of material to write about. 

New York was home for the most part of Dylan’s early career, be it in the city itself or further upstate towards Woodstock, but he couldn’t ignore the growing movement that was taking place on the other side of the coast, in California. 

When the hippie counterculture movement began to really take shape in the mid 1960s, it was San Francisco that played its host, as a concentration of artists took advantage of its somewhat cheap Victorian housing, and banded around there in a bid to reject societal norms. While Dylan wouldn’t exactly be found clad in tie-dye, wandering the streets of the Haight-Ashbury district barefoot, he did ultimately align himself with the city and thus felt somewhat at home there.

In 1966, during an interview with Playboy, he explained how it slotted into his lifestyle alongside New York, saying, “I’m only working out here most, or all, of the time, so I don’t know what this town is really like. I like San Francisco. I find it full of tragedy and comedy”. 

The tragedy and comedy of San Francisco clearly seeped its way into his music of that era, for it was packed with the same sentiments, where his worldly observations were balanced between joy and sadness, capturing the juxtaposed shades of life.

Still, he conceded that New York, for now, was something of a home, noting, “But if I want to go to a city in this country, I will still go to New York. There are cities all over the world to go to. I don’t know, maybe I am just an old dog, so maybe I feel like I’ve been around so long I am looking for something new to do, and it ain’t there. I was looking for some space to create what I want to do. I am only interested in that these days. I don’t care so much about hanging out.”

Dylan dipped his toe into both, truly being someone who never belonged wholly in either. It wasn’t in his nature to outrightly give himself to a place and claim it as his own; instead, his permanency anywhere was deliberately elusive, in the same way his music never assured anything to anybody.

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