Furuta Oribe was a retainer of Toyotomi Hideyoshi, so he learned chanoyu from Sen no Rikyu from an early age. A particularly famous story tells of how Furuta Oribe went with Rikyu as far as Yodo when Rikyu had been censured by Hideyoshi and, accepting that he would have to die, returned to Sakai. After Rikyu's death Oribe became the leading tea master and also became tea advisor to the second Shogun of the Tokugawa family, Hidetada (1579-1632). However, Oribe, like Rikyu, accepted no authority and was richly and freely creative. In particular Oribe's interest in the spirit of kabuki, which was popular at the time and which had an unfixed form and unusual style, became part of his chanoyu. It can be seen in his boldly misshapen tea bowls, for example. Oribe's taste for this kind of unbalance was out of keeping with the new age. After the Osaka summer encampment he was ordered to commit ritual suicide by Tokugawa Hidetada. Oribe's disciple was Kobori Enshu.

Kobori Enshu was Toyotomi Hidenaga's (1540-91) retainer, but he soon became a daimyo under the Tokugawa shogunate. Enshu inherited Oribe's original chanoyu and invented a kind of chanoyu that was suitable for the new age. He did away with the extreme unbalance of Oribe's aesthetic and created a graceful and balanced chanoyu called kireisabi (beautiful worn elegance) which suited the new age of stability. The lineage of chanoyu led by the daimyos (daimyocha) was inherited by Katagiri Sekishu, so that the line of samurai tea masters continued through the Edo period.