Of the three master haiku poets, Issa is perhaps the most beloved. He has been characterized as an ancient Whitman or Neruda or Burns. His poetry can be lively and humorous, pious and honest, or sarcastic and full of rage. He wrote thousands of poems in his life, and many on subjects such as ticks, fleas, frogs and lice.

Much of his work has been judged inadequate and downright bad, but for someone who wrote literally thousands of poems, this is to be expected. However in his best works he presents himself exposed to the world, tender, naked and aware of the pain of life and the suffering of man.

New Year's Day
everything is in blossom!
I feel about average

O flea! whatever you do,
don't jump;
that way is the river

Issa was born Yataro Kobayashi in the mountain village of Kashiwabara in central Japan. His was a family of farmers with literary tastes. At an early age, Issa lost his mother and gained a stepmother. Issa and his stepmother got along terribly and at the age of 14 his father hired him out as an apprentice in Edo. His advice to his son upon his leaving was: "Eat nothing harmful, don't let people think ill of you, and let me soon see your bonny face again."

For his first 10 or so years in Edo, little is known of his activities. Around the age of 25, he emerged, studying haiku and publishing poems under a man named Chikua, who claimed an attachment to the tradition of Basho.

While studying and imitating Basho, Issa formed his own style by "reaching back past Basho to get to Basho." Or, as Issa himself phrased it through, "countrified haiku."

Don't kill that fly!
Look it's wringing its hands,
wringing its feet

(Approaching a village)
Don't know about the people,
but all the scarecrows
are crooked

Issa was championed in the group and after Chikua's death, Issa became its master. His leadership was not appreciated as many considered him a rebel and a year later, at the age of 29, he resigned his position.

Following his father's advice, Issa returned home. Soon thereafter, in the tradition of Saigyo, Basho and Buson, he set off on a ten-year journey, tracing their travels. He shaved his head and wore priestly garb. He also officially took the name Issa, which means "a cup of tea" or "a single bubble in steeping tea." He was financially supported by his father, but earned money by teaching at villages and correcting verse along the way.

He made three specific trips over there ten years and published his travel journals. In 1801, when Issa returned home, his father died. In his will, his father left Issa everything upon the condition he settle there and marry. However, Issa's stepmother and stepbrother contested the will and were supported by their villager neighbors. Issa's journal during this time was published under the title, "A Journal of My Father's Last Days", and has been described as being in a style similar to Balzac.

From "A Journal of My Father's Last Days":

Clear ... as today was the anniversary of the death of the founder of our sect, Father was up early in the morning, and had begun to perform his ablutions. I thought this would aggravate his fever, and tried to stop him, but he would not be dissuaded. Turning to the household statue of the Buddha, he began to read a sutra as was his usual custom. His voice was barely audible. I felt depressed as I gazed from behind at his ravaged form.

With my father
I would watch dawn
over green fields

During the next eleven years, from 1802 to 1813, he was involved in litigation over the will. Issa split his time between his home and Edo, where he taught students and composed the bulk of his work. In the end, in a surprising turn of events, the two warring parties decided to split the house down the middle and live side-by-side.

Issa married a local farm girl named Kiku, which means "chrysanthemum". Their marriage was to be troubled from beginning to end. Over the four years of their marriage, they gave birth to and lost two sons and one daughter. None made it past a year. In 1819, as Kiku was giving birth to their fourth child, she died. Her infant son died soon after.

In a dream
my daughter lifts a melon
to her soft cheek

Chrysanthemums
don't care
what they look like

Four years later, at 63, Issa married again but broke off the marriage. He married a third time in 1825. In 1827, his home burned down and then in November, quite unexpectedly, Issa died, leaving a young pregnant wife. His death poem:

A bath when you're born,
a bath when you die,
how stupid

His daughter, Yata, survived and inherited the rebuilt home, which still remains in her family today.