Jack Kerouac is primarily lauded for his keen understanding of male friendship. The female characters of On the Road or The Dharma Bums never really achieve the reader’s interest the way the males do. But Kerouac is also a writer of exquisitely sad love stories, with complex and fully realized women: The Subterraneans, Maggie Cassidy, and Tristessa. In these tales we find to our surprise that Kerouac was one of the most romantic of American novelists.

The most doomed of these three stories takes place in Mexico City, where Kerouac the narrator finds himself in love with a beautiful girl, an “Azteca, Indian girl with mysterious lidded Billie Holiday eyes.” The problem with this love affair is that she is addicted to “junk.” In some ways she is like the part of Mexico City that Kerouac experiences: sick, dangerous, and poor. But that appeals to the writer in him, and the potential redeemer. He doesn’t try to convince her to stop taking the drugs, but thinks perhaps his love alone can save her. This is a theme that echoes through the history of literature, profoundly romantic and profoundly foolish in the most tragic way. In Tristessa Kerouac brings that theme roaring into the modern age.

Jack himself, of course, is an addict, and he can understand her pain and joy. He says, “I wail on my cup of hiball so much they see I’m going to get drunk so they all permit me and beseech me to take a shot of morphine.” He does, diving in Tristessa’s paradoxical world. He tells us, “Tristessa is a junky and she goes about it skinny and careferee, where an American would be gloomy.” Then he immediately contradicts this and tells us that she complains all day. This complex girl, both magnet and poison, cannot be fathomed, much less rescued.

After leaving Mexico and living the adventures of The Dharma Bums, Kerouac returns to Tristessa, finding her shacked up with his friend Old Bull, a veteran addict himself. She is sicker than ever, and he knows he is too late to save her. She starts to hate him because he is not a junkey, and he realizes that to love her he would have to become one. There is a third person in the love triangle, but it is not Old Bull, nor the Mexican “cats” so attracted to the waifish girl. No, the third side of the love triangle is morphine. Bull preaches the awful truth to Kerouac: “She don’t want love — You put Grace Kelly in this chair, Muckymuck’s morphine on that chair, Jack, I take the morphine, I no take the Grace Kelly.”

With this knowledge Kerouac leaves Mexico City, destined never to find true love. Was he not brave enough, as he claims? Was he unable to reconcile his romantic ideals with cruel reality? Or was he looking for love where it could not be found? We are left to wonder, and left to mourn, as Kerouac does, the loss of the unfathomable mystery of a young girl named, appropriately, Sorrow.

First published at Empty Mirror Books.

Dr. Sax is one of Jack Kerouac’s most troubling books for readers, peering behind the curtain of his childhood rather than exploring those later years of Beats and bodhisattvas. Nevertheless, it remains a startling achievement, unique not only among Kerouac’s works, but among those books that it seems to mirror. It is primarily a book about growing up, similar to such European classics as Alain Fournier’s Le Grand Meaulnes, Hermann Hesse’s Demian, or Jean Giono’s Blue Boy. These books all explore the “magic” of youth by allowing adult readers to see through the eyes of children again, when the magic was real.

Kerouac anchors us in the real world of industrial Lowell with wonderful details like: “The Huge Trees of Lowell lament the July evening in a song begins in meadow and ends up above Bridge Street, the Bunker Hill farms and cottages of Centralville — to the sweet night that flows along the Concord in South Lowell where railroads cry the roundroll — to the massive lake like archeries and calms of the Boulevard lover lanes of cars, nightslap, and fried clams of Pete’s and Glennie’s ice cream…” He also gives us the games and problems of the children that live in that world: “In the bottom of the 8th Scot comes to bat for his licks, wearing his pitching jacket, and swinging the bat around loosely in his powerful hands.” The prose has built up a brick and mortar city and we believe in it. We must, because Kerouac is about to take us into what Alain Fournier called the lost domaine.

As Lowell experiences an epic flood, the mysterious and semi-mythical figure of Dr. Sax swoops into the foreground. He is trying to fight the minions of the great world snake, which is no myth, and really does live curled up underneath the mansion on Snake Hill. This fantastic battle of good and evil is woven into the tapestry of baseball games and ice cream stands. “Blook is a huge bald fat giant somewhat ineffectual who cannot advance through the alley but reaches over his 20-foot arms along the all tops like great glue spreading, with no expression on his floury pastry face — an awful ugh — a beast of the first water, more gelatinous than terrifying.” Suddenly the magic of imagination takes over and the line of actuality wavers and shakes. We picture our own childhood battles with monsters, so much more real and important than a fight on the playground with a bully.

In other books of this genre, the authors always pull us back into adulthood at the end of the book. The loss of childhood is universal, and so the plot ends with the child realizing that he must leave the magic behind, and enter a different world. Not so with Dr. Sax. Kerouac’s literary mirror is from a dark funhouse, twisting the classic logic of the novel of education, leaving the reader unsettled and vexed. Kerouac muses at one point: “Eternity hears hollow voices in a rock? Eternity hears ordinary voices in the parlor.” Those ordinary parlors of Lowell are the place for battles against absolute evil more than some nether realm. And so Kerouac shows us how the fantastic world of childhood is twisted like the great world snake itself into the fabric of reality, and will never let go.

Originally published at Empty Mirror Books.