The first great poet of Odisha is the famous Sarala Das who wrote the Mahabharata, not an exact translation from the Sanskrit original, but a full-blown independent work. Sarala Mahabharat has 152000 verses compared to 100000 in the Sanskrit version. Among many of his poems and epics, he is best remembered for his Sarala Mahabharata. Chandi Purana and the Vilanka Ramayana are also two of his famous creations. Arjuna Das, a contemporary to Sarala Das, wrote Rama-Bibha, a significant long poem in Oriya.

Towards the 16th century, five poets emerged, though there are hundreds year gap in between them. But they are known as Panchashakhas as they believed in the same school of thought, Utkaliya Vaishnavism. The poets are: Balaram Das, Jagannath Das, Achyutananada Das, Ananta Das and Jasobanta Das. The Panchasakhas are very much Vaishnavas by thought. In 1509, Chaitanya, an Oriya devotee of Vishnu whose grandfather Madhukar Mishra had emigrated to Bengal, came to Odisha with his Vaishnava message of love. Before h im Jayadeva, one of the foremost composers in Sanskrit, had prepared the ground by heralding the cult of Vaishnavism through his Gita Govinda. Chaitanya’s path of devotion was known as Raganuga Bhakti Marga, but the Panchasakhas differed from Chaitanyas and believed in Gyana Mishra Bhakti Marga, which has similarities with the Buddhist philosophy of Charya Literature stated above. At the end of age of Panchasakha, the prominent poets are Dinakrushna Das, Upendra Bhanja and Abhimanyu Samanta Simhar. Verbal jugglery, obscenity and eroticism as the characteristics of Shringara Kavyas, became the trend of this period to which Upendra Bhanja took a leading role. His creations were Baidehisha Bilasa, Koti Brahmanda Sundari, Lavanyabati were proved landmark in Oriya Literature. Upendra Bhanja was conferred with the title Kabi Samrat of Oriya literature for the aesthetic poetic sense and verbal jugglery proficiency. Dinakrushna Das’s Rasokallola and Abhimanyu Samanta Simhara’s Bidagdha Chintamani are prominent kavyas of this time