Legends surrounding Ikkyu Sojun tend to circle around two great poles: his contested origins and his radical way of embodying Zen. One popular story portrays him as the illegitimate son of Emperor Go-Komatsu and a lady-in-waiting, with his mother fleeing the court while pregnant to avoid political entanglements. Whether historically secure or not, this imperial-birth narrative functions symbolically, setting up a tension between worldly power and the path of a wandering monk. From early on, tales depict him as a child prodigy, solving difficult riddles and displaying unusual spiritual insight, as if his later iconoclasm were already foreshadowed in youth.

Equally central is the persona he later embraced: “Crazy Cloud,” the monk who refused to separate sacred from profane. Stories describe him drinking in taverns, frequenting pleasure quarters, and openly defying monastic expectations, yet using these very settings as fields of practice. Many anecdotes focus on his intimate relationship with a blind singer—named in different sources as Mori, Shin, or Shinshi—portrayed not as a mere lapse in discipline but as a deep, transformative bond. In these tales, erotic love, companionship, and artistic expression become vehicles for insight into impermanence and compassion, challenging the assumption that awakening must be confined to cloistered spaces.

A further layer of legend presents Ikkyu as a fierce critic of religious hypocrisy and empty formalism. Stories tell of him burning temple images for firewood in winter, remarking that if they were true Buddhas they would leave relics in the ashes, thereby exposing attachment to icons rather than realization. Other anecdotes show him in brothels and streets, delivering sharp, awakening remarks to commoners, embarrassing pompous officials, and undercutting the pretensions of conservative abbots with a single laugh, shout, or rude retort. His self-description as a “blind donkey,” and his claim that his disciples were following a fool, further underline the way he used self-deprecating humor to dismantle conventional ideas of spiritual authority.

Around this iconoclast, more overtly mythic motifs also gathered. Some stories ascribe to him miracles and communication with spirits or ghosts, while others describe him predicting his own death, preparing calmly for it, and meeting it in meditation or with dark, unflinching humor. Tales of a sudden awakening while crossing a bridge and hearing a crow’s call echo the Zen theme of satori arising in the midst of ordinary life. Over time, these strands—imperial birth, wild conduct, erotic devotion, biting satire, and death met without fear—have woven together into the enduring image of Ikkyu as a “crazy cloud”: a wandering, irreverent sage who uses shock, paradox, and everyday experience as instruments of the Dharma.