Bashō was born Matsuo Kinsaku in roughly 1644, somewhere near Ueno in Iga Province. His father may have been a low-ranking samurai, which would have promised Bashō a career in the military but not much chance of a notable life. However, in his childhood Bashō became a servant to Tōdō Yoshitada, who shared with Bashō a love for haikai, a sort of cooperative poetry that began with the 5-7-5 syllable format (now known as haiku) and continued with a 7-7 addition by another poet. Both Tōdō and Bashō gave themselves haigo, or haikai pen names; Bashō's was Sōbō, and he was also given the samurai name of Matsuo Munefusa. In 1662 the first extant poem by Bashō was published; in 1664 two of his hokku were printed in a compilation, and in 1665 Bashō and Yoshitada composed a one-hundred-verse renku with some acquaintances.
Unfortunately, Yoshitada's sudden death in 1666 brought Bashō's peaceful life as a servant to an end. No records of this time remain, but it is believed that Bashō gave up the possibility of samurai status and left his home. Biographers have proposed various reasons and destinations, including the fanciful possibility of an affair between Bashō and a Shinto miko named Jutei. Bashō's own references to this time are utterly vague; he recalled that "at one time I coveted an official post with a tenure of land", and that "there was a time when I was fascinated with the ways of homosexual love", but there is no indication whether he was referring to real obsessions or even fictional ones. He was even conflicted over whether to become a full-time poet; by his own account, "the alternatives battled in my mind and made my life restless." In any case, his poems continued to be published in anthologies in 1667, 1669, and 1671, and he published his own compilation of various authors, Seashell Game (貝おほひ, Kai Ōi?), in 1672. In roughly the spring of that year he moved to Edo to further his study of poetry.
Rise to fame
In Edo, Bashō's poetry was quickly recognized for its simple and natural style. He gave himself the haigo of Tōsei and by 1680 he had a full-time job teaching twenty disciples who published The Best Poems of Tōsei's Twenty Disciples (桃青門弟独吟二十歌仙, Tōsei-montei Dokugin-Nijukasen?), advertising their connection to Tōsei's talent. That winter, his disciples built him a rustic hut and planted a banana tree (芭蕉, bashō?) in the yard, giving Bashō a new haikai and his first permanent home. He wrote hokku in tribute to the Emperor:
- kabitan mo / tsukubawasekeri / kimi ga haru
- the Dutchmen, too, / kneel before His Lordship-- / spring under His reign. 
With this success, however, grew dissatisfaction and loneliness. He began practicing Zen meditation but apparently it did not soothe his fears. In the winter of 1682 the hut burned down, and his mother died early in 1683. He then travelled to Yamura to stay with a friend. In the winter of 1683 his disciples gave him a second hut in Edo, but his spirits did not improve. Instead, after publishing another compilation, Shrivelled Chestnuts (虚栗, Minashiguri?), he left Edo in 1684 on the first of four major aimless wanderings.
Travelling in medieval Japan was immensely dangerous, and at first Bashō expected to simply die in the middle of nowhere or be killed by bandits. As the trip progressed, his mood improved and he became comfortable on the road. He met many friends and grew to enjoy the changing scenery and the seasons. His poems took on a less introspective and more striking tone as he observed the world around him:
- uma wo sae / nagamuru yuki no / ashita kana
- even a horse / arrests my eyes--on this / snowy morrow 
The trip took him from Edo to Mount Fuji to Ueno and Kyoto. He met several poets who called themselves his disciples and wanted his advice; he told them to disregard the contemporary Edo style and even his own Shrivelled Chestnuts, saying it contained "many verses that are not worth discussing." He returned to Edo in the summer of 1685, taking time along the way to write more hokku and comment on his own life:
- toshi kurenu / kasa kite waraji / hakingara
- another year is gone / a traveller's shade on my head, / straw sandals at my feet 
When Bashō returned to Edo he happily resumed his job as a teacher of poetry at his Bashō Hut, although privately he was already making plans for another journey. The poems from his journey were published as Account of a Weather-beaten Skeleton (野ざらし紀行, Nozarashi kikō?). In early 1686 he composed one of his best-remembered hokku:
- furuike ya / kawazu tobikomu / mizu no oto
- the old pond / a frog jumps in-- / water's sound 
Apparently this poem became instantly famous: by April the poets of Edo gathered at the Bashō Hut for a haikai no renga contest on the subject of frogs that seems to have been a tribute to Bashō's hokku, which was placed at the top of the compilation. Bashō stayed in Edo, continuing to teach and hold contests, with an excursion in the autumn of 1687 when he travelled to the countryside for moon watching, and a longer trip in 1688 when he returned to Ueno to celebrate the Lunar New Year. As long as he stayed in his epynomous hut, Bashō would constantly be worrying about inviting over too many visitors and his perceived "idleness". At the same time, he enjoyed his life and had a subtle sense of humor, as reflected in his hokku:
- iza saraba / yukimi ni korobu / tokoromade
- now then, let's go out / to enjoy the snow... until / I slip and fall!