The medieval period in Tamil literature was an out-and-out period of the majestic and royal Cholas, when the whole of south India was governed under one single administration. The period within the 11th and 13th centuries, during which the Chola power witnessed its most inspiring reign, there existed comparatively much less foreign encroachments and daily life for the Tamil people was one of universal peace and prosperity. Chola Empire also provided prospect for the people to interrelate and network with cultures away from their own, as the Cholas ruled over most of South India, Sri Lanka and merchandised with the realms in Southeast Asia. The Cholas also were foremost to erect numerous temples, principally for their preferred god Shiva, and these were celebrated in numerous hymns, to be mentioned in succession.

The Cholas were earnest patrons of Tamil language, single-handedly taking medieval Tamil literature to unprecedented heights. One of the immense figures of Tamil literature, Kamban, precisely belonged to this period. He was the greatest of the court poets of Kulottunga Chola III (1178 - 1218 A.D.). It was Kamban who had adapted Valmiki`s Ramayana into Tamil in his Ramakatai or Kamba Ramayanam, extremely unique in its style and performance. Kamban also had authored other works like Erelupadu and Sathakoparandali.

The other great works of medieval period in Tamil literature comprise - Ottakkuttan`s Uttarakandam (the last canto of the Ramayana), Takkayagapparani and Muvarula; Pugazhendi`s Nalavenba, known also to have popularised the Mahabharata with his simple adaptations in Tamil; Auvaiyar`s Atticcudi, Konraivendam, Mudurai and Nalvazhi; Jayankondan`s Kalingattupparani; Iraiyanar`s Kalaviyal; Kalladanar`s Kalladam, Aiyanar Itanar`s Purapporulvenbamalai, Puttamittiranar`s Viracozhiyam, Divakarar`s Divakaram, Pingalar`s Pingalandai and Pavananti`s Nannul. Another important poet who had prospered to booming during the Chola period was Kuttan, who had penned unforgettable works like Nalayirakkovai, Parani, Tukkayagapparani, Sarasvatiyandadi and Arumbaittollayiram. Chayam Kontar had penned an extensive war poem Kalingattu Parani, in the Sangam style. Jain writers had produced didactic works, grammatical treatises and lexicons from time to time. The following centuries were the age of learned commentaries on Sangam poetry, Shaiva and Vaishnava philosophies, and literature influenced by Sanskrit. Other distinguished scholars of the Chola period include Tirutakadevara, author of Jiwana Chintamani and Talamokti, author of Sulamani and Venkatamadhava, who penned a commentary on Rig Veda during the rule of Parantaka I.

Some of the Sanskrit influenced write-ups in medieval Tamil literature were the esteemed Bharatham by Villiputthurar, Thiruppuhazh (hymns) by Arunagirinathar and translations of umpteen Puranas. Some brilliant stray verses from this period have been collected in late anthologies like Kalamegham, Satthimutthapulavar and Padikkasu Thambiran. European Christian missionaries also took to Tamil in the 16th century, and the first book was printed in 1579. Muslim poets like Sakkari Pulavar and Umaru Pulavar brought in new themes in Tamil writings in the 18th century.

The Prabhanda became the dominant form of poetic rhythm. The religious canons of Saiva and Vaishnava sects were beginning to be compiled and categorised in a systematic manner. Nambi Andar Nambi, who was a contemporary of Rajaraja Chola I, compiled and formatted the books on Saivism into eleven books referred to as Tirumurais. The hagiology of Saivism was lend a standardised appeal in Periyapuranam (also acknowledged as Tiruttondar Puranam) by Sekkilar, who existed during the reign of Kulothunga Chola II (1133 - 1150 CE). Religious books on the Vaishnava sect were mostly framed in Sanskrit during the medieval period of Tamil literature. The great Vaishnava leader Ramanuja lived during the reigns of Athirajendra Chola and Kulothunga Chola I, and had to confront religious maltreatment from the Cholas, who was a Saiva faithful by nature. One of the best known Tamil works from this period is the Ramavatharam by Kamban, who flourished during the reign of Kulottunga III. Ramavatharam is reckoned as the greatest epic in Tamil Literature, and although the author expresses that he complied with Valmiki, Kamban`s work is not just a translation or even an adaptation of the Sanskrit epic Ramayana; Kamban had successfully brought into his narration the colour and backdrop of his own times. A contemporary of Kamban in medieval Tamil literature was the legendary and celebrated poetess Auvaiyar, who derived utmost pleasure in writing for young children. Her works, Athichoodi and Konraiventhan are even now generally read and taught in schools in Tamil Nadu. Auvaiyar`s two other works, Mooturai and Nalvali were penned for slightly the not-so-young ones. All the four works are didactic in temperament; they elucidate the basic wisdom that must govern commonplace and unexciting life.

From amongst the books based upon Buddhist and Jain faiths, the most noteworthy is the Jivaka-chintamani by the Jain ascetic Thirutakkadevar, framed in the tenth century. The Viruttam style of poetry was used for the very first time for verses in this book. The five Tamil epics, consisting of Jivaka-chintamani, Cilappatikaram, Manimekalai, Kundalakesi and Valayapathi, are collectively known as The Five Great Epics of Tamil Literature. There were also a number of books written, based upon Tamil grammars. Yapperungalam and Yapperungalakkarigai were two treatises on prosody by the Jain ascetic Amirtasagara. Buddamitra penned Virasoliyam, another work on Tamil grammar, during the reign of Virarajendra Chola. Virasoliyam endeavours to establish a synthesis between Sanskrit and Tamil grammar. Other grammatical works from medieval Tamil literature period comprise: Nannul by Pavanandi, Vaccanandi Malai by Neminatha, and the commentaries on the Puranic theme, Purapporul Venpamalai by Aiyanaridanar.

Medieval Tamil literature also assimilated biographical and political works, such as Jayamkondar`s Kalingattupparani, a quasi-historical account on the two invasions of Kalinga by Kulothunga Chola I. Jayamkondar was a poet-laureate in the Chola court and his work is an excellent instance of poise between fact and fiction the poets had to stride. Ottakuttan, a close contemporary of Kamban, penned three Ulas extolling Vikrama Chola, Kulothunga Chola II and Rajaraja Chola II.