Contemplating Cassady

Contemplating Cassady

The Peculiar Appeal of the Rebel Muse — Are you you? Or are you who it/they/the system wants you to be? A look at the enduring appeal of Neal Cassady and the rebel muse.

’I know you rider, gonna miss me when I’m gone’ – traditional blues song, covered by the Grateful Dead.

Woe be to ye who follow the way of the Holy Goof, for your reward, well, it isn’t likely to be earthly – at least not as it’s been sold. And for it to be something else, you’re going to have to believe in something else. And if you don’t, you’re just going to have to believe that living like the Holy Goof is the right way to live; that your reward will be life itself.

Kerouac’s personification of Neal Cassady, aka Dean Moriarty, as his Holy Goof refers back to the apostle Paul who tells the Corinthians that he and his crew are fools for Christ, a ragged band, despised, ‘made as the filth of the world’. In other words, they’re beat. Their poverty and their lack of interest in the trappings of polite society has made them pure.

As Dean Moriarty said to Sal Paradise – or as Cassady said to Kerouac – ‘Everything is fine, God exists, we know time. Everything since the Greeks has been predicated wrong. You can’t make it with geometry and geometrical systems of thinking. It’s all this!’

Sal, though, is in limbo. Somewhere between Paul and the Corinthians. Somewhere between Dean and dreams of a house with a white-picket fence. Somewhere between Whitman’s wild, pure America and the America of Sloan Wilson’s The Man in the Gray Flannel Suit, which would come out just a year before Jack Kerouac’s On The Road.

Dean’s life – his glory and his folly – puts the question right to Sal, just as Neal Cassady likely did to Kerouac. How d’you want to live, son? Is it this, or is it that? Are you you? Or are you who it/they/the system wants you to be?

This is a question American men have been struggling with since the frontier closed and the farms became mechanised and cities, suburbs and exurbs became the country’s organising principles. Wilson’s book suggests you can be both; that you can maintain some internal integrity while selling out on the surface. Some call it adulthood. But I’m not sure. It’s a rift I have yet to settle within myself, despite having been around for nearly half a century, almost as long as the Holy Goof, Moriarty, has been On The Road.

I know you rider.

I moved six times by the time I was ten: out of state, out of country, back in country, south, north, bottom to middle to top. By the time I was thirty-one, I had moved seventeen times. West, further west, north, south, east, west again, west again.

This peripatetic existence might have worn out Kerouac himself, and looking back it was most definitely the same quest for self-knowledge and god-knowledge that inspired Dean and Sal’s adventures, but it was also the result of schizophrenic vacillation between the two sides of myself I couldn’t, like the hero of The Man in the Gray Flannel Suit, reconcile. I yearned for comfort, for a home and a hearth somewhere away from the chaos I came from, but I also put the possibility in my rearview mirror every time it finally seemed within my grasp. Some Cassady in my ear always seemed to shake me up and send me on my way just when I was getting somewhere. The real me, he said, was out there somewhere. I just hadn’t found him yet.


College was my first stab at convention. I went to a pricey school that specialised in turning out future masters of the universe who consistently voted Republican and worshipped America without, it seemed, knowing it very well.

Which could explain why I gravitated to the great Drozini. Drozini was a couple years older than I. In a school populated with preps, he dressed in tattered flannels and jeans. His hair was never combed and hardly ever washed. He wore a long, black wool overcoat that shrouded him in mystery. He was a superstar high-school athlete who blew out a knee and then smoked excessively. He had an unmatched stamina for drink and drugs. He spoke in parables (“Take two or it’s not worth it”) and refused to give a shit about the relentless strivings going on all around us. Like Jack, his father was dead and I knew, somehow, that this was the centre of his sadness.

I’d drive with him in the sullen, snow-dusted valleys of Chenango County and down into green Pennsylvania, through Maryland, and into all of the nameless mid-Atlantic. Like Cassady, he was a moocher and a con. The poorest guy at our rich school, perhaps. A user. I’d drop him off at his mother’s house. She’d feed us and show pictures of Drozini from high school when he ruled the known world. The hallways of that house were haunted in black and white and the world outside was getting less known all the time.

Drozini changed my course. Or confirmed it. I’m not sure. Like Kerouac, he was a master at showing and not telling, leaving his audience to its own imagination.

As I was at school on athletic grants, I quit the jock life and started reading novels and history books. Philosophy. Grew more curious about the world west of the Hudson River than most of my now very successful friends. I kept moving, shuffling, searching for me and god and reinventing myself along the way. I shook my fist at the sky a lot.

In the process I became a dilettante of the American margins, seeking subcultures and trying them on for size. I’d excavate for artefacts of Lou Reed’s Lower East Side. When that ran its course, I’d go to the mountains and cop the persona of Craig Kelly, fashion myself a soul rider in harmony with the elements, no parks or pipes, only the mountain. In the West Coast cities, I’d study the legends of Miki Dora and Jay Adams, cop their personas, hitch their rides. In the bars I was Bukowski, brawling and breaking noses, mostly my own.

Who were these American archetypes and who was I among them? What is the content of our character more than fifty years after On The Road posed the question? Are we holy fools or are we company men? Do we go bop or go bang? And, as Carlo Marx said to Sal and Dean, ‘I mean, man, whither goest thou? Whither goest thou, America, in thy shiny car in the night?’ And to which Dean answered back, ‘Whither goest though?’

Yes, whither, indeed.