Show caption ‘Boy, it’s been a lot of fun around here’ … Jack Kerouac. Photograph: Sotheby's Jack Kerouac Jack Kerouac letter to mother recounts ‘On the Road’ adventures Written 10 years before the book that defined the Beat Generation, appeal for a $25 sub is now on sale in California for $22,500 David Barnett @davidmbarnett Thu 20 Sep 2018 09.08 EDT Share on Facebook

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He may have been the godfather of the Beat Generation, a self-styled crazy hobo mystic who hit the US’s highways looking for himself, but Jack Kerouac wasn’t above asking his mother for money to tide him over on the epic journey he immortalised in On The Road.

In a letter from 1947, written at the height of the travels that would form the basis of his classic roman a clef published 10 years later, Kerouac begs his mother, Gabrielle, for $25 to help him get from Denver to California.

The handwritten note, dated 29 July, was written when Kerouac was 25, and is being sold through online bookseller Abebooks by Pasadena-based rare book dealers Whitmore for $22,500 (£17,000).

The letter betrays a vulnerability in the young Kerouac perhaps overlooked by those who only know him as the free-wheelin’ author of counterculture classics. Opening the note, written in pencil, he begins “Dear Ma”, and gives Gabrielle instructions on how to wire the money to him from a Western Union branch near where she works in Brooklyn.

Kerouac’s 1947 letter to his mother, Gabrielle. Photograph: Whitmore Rare Books

However, despite saying he needs it because “hitchhiking is impossible across the desert and mountains”, Kerouac isn’t exactly living in squalor in Denver, writing: “I’m staying in a swanky apartment with showers and food and everything. But I want to get going so I can make a lot of money sailing in the Pacific and come home in the Fall and finish my book.”

In a particularly tender line, Kerouac writes: “Gee, you can’t realise how much I miss you, and the house, and writing in my room. But I’ll be back in a few months and we’ll save some money.”

Signing the letter “Jacky”, with three kisses, Kerouac also regales his mother with some of the adventures in Denver that were later detailed in On The Road: “Boy, it’s been a lot of fun around here … I had about 10 girlfriends; went up to the mountains; saw an opera; ate swell food, venison steak.” Despite – or perhaps because of – all that, he says “I haven’t a cent left”.

The Denver episode is an important one in the Kerouac legend, as it was the first real road trip he took and was rehearsed in On the Road. Denver was also the home town of Neal Cassady, the “side-burned hero of the snowy West” who was part best pal, part muse to Kerouac.

In On the Road, in which Kerouac’s mother Gabrielle appears as the aunt of his alter-ego Sal Paradise, he directly references this letter: “I sent my aunt an airmail letter asking her for fifty dollars and said it would be the last money I’d ask; after that she would be getting money from me, as soon as I got that ship.”

When Kerouac did get to San Francisco to visit his friend Henri Cru, who appears in On the Road as “Remi Boncoeur”, his planned merchant seaman career never materialised. Kerouac ended up working as a security guard on a construction site.

According to Whitmore Rare Books, the note “undermines the notion that the road trip was aimless. As he charts his path west, he plans out money and transportation, telling his mother about the need for efficiency if he’s going to meet his goals”.