WRITING TO ALLEN GINSBERG in October 1956 from one of his transits of Mexico, Jack Kerouac broke a rueful mood to declare:

Only good thing is I started to paint — I use house paint mixed with glue. I use brush and fingertip both, in a few years I can be topflight painter if I want — maybe then I can sell paintings and buy a piano and compose music too — for life is a bore.

Within a few years, Kerouac was producing a range of oils, watercolors, and pencil sketches — all contained in this fascinating and treasurable volume.

Kerouac: Beat Painting is the catalog of an exhibition mounted, between December 2017 and April 2018, at the MAGA Gallery at Gallarate in northern Italy. While it was by no means the first show of visual art by the Beat writers, it did open a revelatory new door on the aspirations of Kerouac during a key period in his career. Having experienced some light training at Dody Muller’s studio in New York, he displays in many of the best works collected here an expressionist sensibility reminiscent of Willem de Kooning, as well as a Post-Impressionist recourse to vivid improbabilities of color. In short, Kerouac the painter turns out to be every bit as interesting as Kerouac the writer.

A set of oil portraits forms the startling introduction. The high domed head and riveting gaze of Cardinal Giovanni Montini, the future Pope Paul VI (after a photograph in Life magazine), has the autocratic weight of a Velázquez pontiff. The painting is a study in ecclesial crimson, in which the dangled black cappello and the pectoral cross compete for attention with the piercing blue of the apprising eyes and the tomb-like yellow of the brow. In another portrait, Truman Capote, who famously dismissed Kerouac’s compositional technique as mere “typing,” is rewarded for his vitriol with a violent Vorticist swirl of muddy pigment that seems to hint at the famous photograph by Roger Higgins in which Capote clutches his over-exposed face. By contrast, William Burroughs is instantly recognizable, oiled in dense impasto profile in his fedora, a hook of sodium-yellow outlining the black dilated lake of one eye, and again in a pastel line drawing that traces the fellow writer’s bespectacled visage from sparse, disordered hair to pointy chin.

Woman in Blue with Black Hat offers a Matissean monument to the chance occurrence, recorded at length in Visions of Cody (1972), through which Kerouac and Neal Cassady stumbled onto the film set of David Miller’s noir masterpiece Sudden Fear (1952), starring Jack Palance and Joan Crawford, the portrait’s subject. The actress is depicted in cornflower blue in classic Hollywood contrapposto, one eye obscured by a millinery creation akin to Cardinal Montini’s cappello, black-gloved hand at hip, the other preparing to jam a cigarette into the glutinous scarlet oblong of that never less than terrifying mouth.

Kerouac’s spiritual sensibility in the last two decades of his life was imbued with what the catalog calls a religious “syncretism,” manifesting as a troubled adherence to the Roman Catholic faith of his French-Canadian roots, refracted through a preoccupation with an imperfectly assimilated Buddhism. The religious works included here revert to a childlike graphic style: a spooky archangel Raphael floats above the table of Tobias; a glowing Madonna is rendered in thickly scrawled pencil lines; Judas dangles from his gallows like the stick figure in a schoolboy’s game of Hangman.

The most striking suite of paintings is a series of undated pictures, all probably from the late 1950s, done in liberally applied oil on canvas. A reclining nude shielded by a guitar lies before an ornately canopied bed, against a backdrop that seems to open into a Claude-like vista of framing trees and sky. A blonde in a green dress, almost perfectly camouflaged against the grass on which she sleeps but for her golden head and lower legs, is contrasted with the foreboding of the glowering forest and nighttime sky that occupy the upper half of the canvas. An image of empty fishing boats at the turbid water’s edge at the onset of twilight is almost photorealistic, but for the insertion of a febrile, egg-yolk yellow sunset out of Munch.

Contributors to the volume situate Kerouac’s artwork in the context of his literary production and spiritual quests. Sandrina Bandera meticulously documents the art-historical traces discernible in his paintings and drawings — a heady mix of Christian and Buddhist images, biblical subjects from the Italian Renaissance, pre-Columbian codices, and the work of Picasso and the Abstract Expressionists. According to Bandera, Kerouac’s labor in seeking a style is ultimately more important than its discovery:

There is something about these artworks that alludes to the unfinished […] as if they really were trial runs, while in reality they already belong to Kerouac’s poetic universe: that world in which all is fleeting and must be caught, instantly, before one moves on to future experiences.

In a fine essay, Franco Buffoni examines the writer’s pursuit of rootlessness in an effort to find true communion with the world. Buffoni situates Kerouac’s constant journeying in a tradition that runs from the ascetic odyssey of St. Francis all the way to the doomed solo voyage of Chris McCandless, the American traveler who perished alone in Alaska in 1992 (as portrayed in the 2007 biopic Into the Wild). Such a desperate end is “the extreme consequence,” says Buffoni, “of the philosophy underlying On the Road.”

“Kerouac demonstrated that all of life is creation,” writes Francesco Tedeschi, “a hunger for something unreachable and unstoppable.” This journey would culminate, notoriously, in an alcoholic dead end, but the author’s persistent urge to avoid the narrow path and the settled destination is on full display in the astonishing heterogeneity of this indispensable collection.

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Stuart Walton is a cultural historian and novelist.