“Ikkyū is my true heir, but his ways are wild”: these words, uttered by the fourteenth-century Zen master Kasō, may seem like something of an understatement to those acquainted with his chosen successor. Legends about Ikkyū abound to this day, making it difficult to separate truth from Tokugawa Period invention. The bastard son of Emperor Go-Komatsu, Ikkyū was sent to live at Ankoku-ji Temple when still a child and would soon gravitate toward the austerer strains of Buddhist thought. At twenty-one, grieving the death of his first great teacher, he paddled out to the center of Lake Biwa intending to drown himself but was stopped by the ghost of his mother. Years later, adrift in a boat on a different lake, he would hear the sound of a crow’s call and achieve enlightenment.

A man of iconoclastic extremes, Ikkyū adopted the pen name Mad Cloud (Kyōun), authored verses that smash scriptural references together with scatalogical content, and spurned the comforts of his home monastery’s main buildings for a hut he dubbed Blind Donkey Hermitage. He is perhaps most famous, however, for his unabashed love of wine and women. In artworks, Ikkyū is often depicted flanking the Hell Courtesan, Jigoku Dayū, whose name punningly references both the highest (dayū) and lowest (jigoku) rank of Edo Period sex workers, the latter of which is also the Japanese word for the demon realm. A legend recorded in Santo Kyōden’s All Records of Drunken Enlightenment of Our Country (Honchō Suibodai Zenden, 1809) relates how Jigoku Dayū began her path toward spiritual advancement after meeting Ikkyū in the brothel where she worked. Many prints of the two feature the monk with an incongruously serene smile pasted across his face as he lofts a skull above the lady’s head.

It is this fame for sinner-sainthood that, at least in the popular imagination, has eclipsed Ikkyū’s significant achievements as an artistic jack-of-all-trades: as a shakuhachi (bamboo flute) player, as a calligrapher, as a practitioner of ink painting, and as a writer. Many of these skills are brought to bear in his book Skeletons (Gaikotsu, ca. 1457), a mixture of poetry and prose that comes down to us in printed editions supposedly replicating a manuscript, now lost, by the monk’s own hand. The text describes a series of visions of animated skeletons that Ikkyū had when he visited an abandoned temple. The lively illustrations testify to their maker’s sardonic sense of humor: he images skeletons dancing, drumming, drinking sake, having sex. In the verse, too, we see glimpses of the monk’s trademark irreverence:

If a stone
Can be the memento
Of the dead,
Then the tombstone
Would be better as a lavatory.

Ikkyū lived during the Muromachi Period, when close ties between the Ashikaga Shogunate and Kyōto’s temples resulted in a flush monastic class quite far from the ascetic ideal of the sangha to which Ikkyū cleaved. As many have pointed out, the monk’s life also coincided with a time of virtually constant conflict — including the devastating Ōnin War — that laid Kyoto to waste amid horrific scenes of violence and upheaval. For all that Skeletons’ titular apparitions frolic and cavort across the page, the dominant tone of the text is one of melancholy and somber contemplation. A number of its poems reference Mount Toribe, whose well-known cremation grounds outside the Kyoto city limits served as a memento mori for the capital’s residents each time they saw its ascending column of smoke. “When the breathing stops and the skin of the body is broken there is no more form, no higher and lower”, Ikkyū writes, cautioning readers about both the fleetingness of existence and the ultimately illusory nature of all things. A similar idea is expressed in certain versions of the Jigoku Dayū tale in which she witnesses Ikkyū dancing with a group of her fellow courtesans: when the group goes behind a screen, the lady is startled to see their solid bodies project ghastly skeletal shadows, as though their flesh had melted away in an instant to reveal a premonition of the death that awaits us all.

As time went on, Ikkyū would become increasingly disillusioned by the corruption and worldliness of monastic authorities. In this context, his famous eccentricities begin to take on a different feeling: better to spurn the pieties professed by hypocrites than to submit to the fossilized non-thought of convention. The nickname Mad Cloud was less a sincere self-appraisal, as the Japanese literature scholar Sonja Arntzen explains, than “a way of pointing out his supramundane sanity” amid an ailing establishment increasingly removed from the values it pretended to espouse. In 1447, despairing of the intrigue and backbiting at his home monastery, Ikkyū hiked up to a remote mountain retreat with the intention of starving himself to death. He was saved this time not by his dead mother but by a living cousin, a distant half-relation who had come to occupy the imperial Chrysanthemum Throne in the meantime. Legend has it that this cousin dispatched an emissary begging Ikkyū to desist for the sake of the soul of the nation — by which one might suppose, substituting body natural for body politic, that the emperor meant also for the sake of his own soul as well.