Sugawara no Michizane ranks among the best-known poets of the Heian period, although he must be among the least often read. Through the Nara period, Michizane's ancestors had served as minor officials at court. The move of the capital to Heian marked a change in the family's fortunes. By the time of Michizane's birth, the Sugawara were known as a family of court scholars. In Michizane's world, scholarship meant a form of Sinology that combined mastery of the Chinese classics with the ability to make practical use of such knowledge. Compositions included both prose and poetry, both official documents and personal expressions. Michizane also wrote waka and associated with some of the major waka poets of his day. Most of Michizane's prose consists of official documents and religious writings, often drafted for others less skilled at composition in Chinese. In Japanese, one rarely wrote of love for one's children. In Chinese, Michizane wrote very affecting poems on that subject.

The three most frequently commented texts of the classical literary canon are Kokin wakashu or KKS, Ise monogatari or The Tales of Ise, and Genji monogatari or The Tale of Genji. Imperial waka anthologies for the three centuries after KKS were ignored by commentators until the eighteenth century; the same is true for The Tale of Sagoromo, a narrative fiction the waka of which were considered comparable to those of Genji in late Heian and Kamakura times. One factor must be that KKS and Tales of Ise themselves incorporate distinctive forms of commentary. KKS can be defined in fact as a corpus of cited poems framed by two kinds of editorial comments and two "prefaces". The earliest extant commentaries on The Tales of Ise inclined toward extravagant allegoresis incorporating strains of Esoteric and Tantric Buddhism and Shinto that flourished in the thirteenth and fourteenth centuries, often intertwined with heterodox KKS commentaries of a similar bent.

Recluse literature, and the related label "thatched hut literature" are terms coined in the twentieth century to describe works in a variety of genres, such as waka, setsuwa, and zuihitsu, by a broad array of authors of the medieval period. Saigyo, Kamo no Chomei, and Yoshida Kenko exemplify the recluse ideal while problematizing the idea and practice of isolation. By the end of the Heian period, the trope of reclusion in waka was dominated by nuns, many of whom had been imperial women at court. Chomei's language reflects the trend in recluse literature to conflate the poetic diction of the four seasons with the language and concepts of Buddhism making nature not only the great mirror of human emotion but also a manifestation of the Buddhist Dharma. Kenko came from a Shinto family of priests and diviners. Medieval recluse literature chronicles the numerous forces that pulled hermits and travelers both toward and away from the poles of the sacred.

The first extant setsuwa collection is the aforementioned Nihon ryoiki, a Buddhist collection edited and compiled in the early Heian period. Godansho is a setsuwa collection that records stories narrated by Oe no Masafusa, one of the leading scholars and poets of the time. The systematic attempt to provide knowledge of the past, particularly of the aristocratic past, is evident in Kokon chomonju, which was edited around 1254 by Tachibana Narisue, a low-ranking aristocrat and literatus who received the secret transmission on playing the lute. Since one of the objectives of setsuwa collections such as the late Heian period Konjaku monogatari shu, edited by Gento, was to provide an encyclopedic worldview, centered on India, China, and Japan, these collections included stories from these three countries. The Kara monogatari, a late-Heian period setsuwa anthology perhaps edited by Fujiwara Shigenori, is a collection of poem-tale style adaptations from Chinese texts.

Much longer fiction survives from Imperial Princess Baishi's day, and one of her attendants, is credited with Sagoromo monogatari, dated to sometime between 1069 and 1086. The influence of Genji is discernible on the very first page of Sagoromo, as the eponymous hero alludes to a poem by Genji himself. In the postscript to his copy of the Sarashina nikki, the famous poet Fujiwara no Teika records the attribution of four monogatari to the diary's author, two of which are still extant: Yoru no Nezame and Hamamatsu Chunagon monogatari. The final monogatari extant from the Heian period is Torikaebaya monogatari. Critical consideration of the monogatari genre reached its second peak in 1271 with the completion of the Fuyo wakashu, an imperial anthology-like collection of over two hundred poems drawn exclusively from monogatari, in twenty books. The collection provides evidence that it was in fact in the Kamakura period that most monogatari were produced.

Kyogen is Japan's classical comic theater, and also Japan's oldest dialogue-based drama. The earliest precursors to kyogen plays are thought to be irreverent skits performed along with court dances in the Nara and Heian periods. From the early 1400s Zeami and other leaders of noh troupes brought kyogen performers under their organizational umbrella, and kyogen plays have been performed as comic interludes between noh plays from that time until today. The most popular play in the current repertory, Delicious Poison, is one of the few for which one can identify an original literary source. As in the noh drama, kyogen developed many conventions of staging. The kyogen repertory stands as medieval Japan's secular and playful counterpart to the harsh, formal social values intended to govern the lives of Japanese. The core of much kyogen humor is in parody, which deconstructs and inverts specific texts or social types and norms. Kyogen maintained its traditional repertory and functions through World War II.