This interdisciplinary work combining the knowledge of both History and Music exhibits two separate moods of challenge faced by Hindustani music originating in twelfth century north India. The first one was the challenge against musicological orthodoxy of the ancient period. It was the latter half of the 18th century when the British Orientalist thinkers like William Jones, Warren Hastings, and Augustus Willard etc. being motivated by their Sanskrit-fascination endeavored to explore the ‘classical’ music treatises of ancient India and blamed the Hindustani music of medieval north India was caught in their eyes as a symbol of ‘cultural degeneracy’ of medieval ruling class. And the other one is, challenge against social orthodoxy. Whereas there was a Brahmanical monopolization upon the ancient Indian classical music, how Hindustani music despite being created by the elite section became a part of people’s music by its language and contents has been taken place in this paper. Though Hindustani music is a vast field of study, two leading genres of Hindustani music i.e. Dhrupad and Khyal have been focused on specially and some influential musical experimentalists of medieval India have been selected to be analyzed in order to reach the final consideration.