Issa was born and registered as Kobayashi Nobuyuki, with a childhood name of Kobayashi Yatarô, the first son of a farmer family of Kashiwabara, now part of Shinano-machi, Shinano Province (present-day Nagano Prefecture).
Issa endured the loss of his mother, who died when he was three. Her passing was the first of numerous difficulties young Issa suffered. He was cared for by his grandmother, who doted on him, but his life changed again when his father remarried five years later. Issa's half-brother was born two years later, and when his grandmother died when he was 14, Issa felt estranged in his own house.
Issa was a lonely, moody child who preferred to wander the fields. This attitude did not please his stepmother, a "tough 'managing' woman of hard-working peasant stock." Issa’s difficult relationship with his stepmother would continue until his latter years.
In 1777, Issa was sent by his father to Edo (present-day Tokyo) to eke out a living. Nothing of the next ten years of his life is known for certain. His name was associated with Kobayashi Chikua of the Nirokuan haiku school, but their relationship is not clear.
In the following years, Issa wandered throughout Japan while fighting over his inheritance with his stepmother (his father died in 1801). After years of legal wrangling, Issa managed to secure rights to half of the property his father left. He returned to his native village at the age of 49 and soon took a wife, Kiku. After a brief period of bliss, tragedy returned. The couple's first-born child died shortly after his birth. A daughter died less than two-and-a-half years later, inspiring Issa to write this haiku (translated by Lewis Mackenzie):
Tsuyu no yo wa tsuyu no yo nagara sari nagara
The world of dew --
A world of dew it is indeed,
And yet, and yet . . .
A third child died in 1820, and then Kiku fell ill and died in 1823. Issa married twice more late in his life, and through it all he produced a huge body of work.
The final event in Issa’s sad and tragic life occured in July of 1827. Fire swept the post station of Kashiwabara and Issa lost his house in the blaze. He was then forced to live in his storehouse, which is still kept in the town.
Kobayashi Issa died on January 5, 1828, in his native village.
In his lifetime, Issa wrote over 20,000 haiku, which have won him readers up to the present day. Though his works were popular, he was never wealthy because of it.
Despite a multitude of personal trials, and tragic events his poetry reflects a childlike simplicity, making liberal use of local dialects and conversational phrases. His works also include haibun (passages of prose with integrated haiku) such as Oraga Haru ("My Spring") and Shichiban Nikki ("Number Seven Journal"), and he collaborated on more than 250 renku (collaborative linked verse).