Born on the fifth day of the fifth month of 1763 (Horeki 13) as the eldest son of a middle peasant family in Kashiwabara, a post town on the Hokkoku Highway in northern Shinano (today Kashiwabara, Shinano-machi, Kamiminochi District, Nagano). His given name was Kobayashi Yataro, common name Nobuyuki. He lost his mother at three; not getting along with his stepmother, he was sent to Edo as a servant at fifteen. In Edo he studied haikai under the Katsushika school poet Niroku-an Chikua. From 1792, for seven years from age 30, he traveled the western provinces, Shikoku, and Kyushu, polishing his own style. In 1801, on the death of his father, he returned to his native Kashiwabara, but a 13-year dispute with his stepmother and half-brother over the inheritance was only settled in 1813; for the first time in his life Issa settled in his hometown. In 1814, at 52, he married 28-year-old Kiku and they had three sons and a daughter, but the children all died young. His wife Kiku too died of tuberculosis in 1823 at 37. He remarried in 1824 but divorced after little more than two months, and married a third time (Yao) in 1826. In June 1827 the great fire of Kashiwabara destroyed his main house and he lived in his storehouse, where on the 19th day of the 11th month of 1828 (Bunsei 10) he died at 65. He composed more than 20,000 verses in his life and stands with Basho and Buson as one of the three great haiku poets of the Edo era.

Out of a life that knew suffering through and through, he held an inexhaustible compassion for the weak — skinny frogs, baby sparrows, ants, flies — a gentleness joined to a stubbornness that could fight for thirteen years over inheritance in his hometown. With the warm gaze of plain colloquial speech in such verses as 'Come and play with me, sparrow with no parents,' 'Skinny frog, do not lose, here is Issa,' and 'Baby sparrow, get out of the way, the noble horse is passing,' his style has a uniqueness quite different from Basho's wabi-sabi or Buson's painterly world.

One of the three great haiku poets of the Edo period together with Basho and Buson. Of about 20,000 verses he composed in his life, around 2,000 are preserved today. His style, full of sympathy for the weak, the common people, and small creatures, influenced many poets from Shiki onward in the Meiji era and after, and he remains one of the most frequently chosen poets in textbooks today. In Shinano-machi, Nagano, the Issa Memorial Museum and the Haikai-ji (the storehouse where Issa died) stand, and on the anniversary of his death every November 19, haiku poets and lovers gather from all over the country. The Kurohime Highland near his birthplace has become a pilgrimage site for haiku lovers.