Newly Discovered Jack Kerouac Letters Shed Light On His Teenage Years

Spoiler alert: they're almost all about girls.

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If you’re a fan of the Beat Generation and the On the Road author who is often synonymous with it, then you’ll be interested to know that a treasure trove of Jack Kerouac letters has been discovered. Guardian reports that new light is surfacing on the teenage years of Kerouac, based on 17 letters, two postcards and seven fragmented writing pieces that the daughter of George Apostolos, a childhood friend of Kerouac, found after her father died. Kerouac wrote to Apostolos from Horace Mann, the New York City prep school he attended, and from Columbia University, largely between 1940 and 1941, meaning he would have been in his late teens when he put pen to paper. The letters show the teenage author emotionally invested and head over heels for the lady folk, in addition to foreshadowing some serious literary talent.

Take this entry, for example, in which Kerouac is describing the sister of a friend he was intent on marrying: “There is no doubt in my mind that you or I have never laid our eyes on such an exquisite creature as Jacqueline Sheresky. Her neck has that stamp of blueblood; it curves up delicately and like ivory to a perfectly moulded almond chin, and thence to quivering scarlet lips, covering a row of alabaster teeth. Her eyes are dark as ebony, with a flash of fire in them. Her hair topples down in rippling cascades of black sleekness, over a pair of resilient, lush shoulders. She is slim, blooming and graceful; I have never seen anything like it.”

It’s entertaining to read about Kerouac’s troubles with the ladies in the 1940s with excerpts like the following: “The trouble with me is, that I haven’t the nerve to ask her to the Senior Prom … Were I to escort this Goddess to the Waldorf, I would have my measure of life poured into one night…I am afraid that God-damned Jew Sokolow has already asked her.” Sounds like the plot of an ABC Family drama, no?

Skinner is the auction house that will handle the letters, which will go up for sale on November 16. “In these letters Kerouac comes through as playful and brilliant, an eager student who seems perfectly at home first in the unfamiliar prep school culture at HM, and later as a freshman at Columbia,” the auction house said in a statement. “He socializes, plays football, writes, reads, speculates, philosophizes, and imagines his own future.”

The letters are expected to go from anywhere between $2,000 and $5,000 each. Perhaps teenagers today should follow suit?

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