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Resistance has always been directly related to courage. .Mark Twain was of the view that courage is resistance to fear, it is mastery on fear and not absence of it. The paper explores the lives and times of two subcontinental women artistes – – Gauhar Jaan of India and Iqbal Bano of Pakistan who lived life on their own terms. Their lives are more than narratives of personal experiences. Each one’s life was a testimony on the way historical and political events had impacted their lives. Creativity in the arena of music has ever been the prerogative of men and it has always been associated with masculinity. Hence many women, despite possessing creative talent, have had to take a back seat and pursue music only as a hobby. The paper focuses on these two women artistes who defied conventions by attempting to pursue music all their life. Gauhar Jaam 91873 – 1930), an Indian singer and dancer from Kolkata redefined Hindustani classical music by incorporating technology with it which most men artistes were afraid to experiment with .She flouted government resolutions in Kolkata and would go around in her four horse driven buggy for which she even paid an amount of a thousand rupees to the viceroy as fine. Iqbal Bano (1935 – 2009) resisted and challenged the Zia – ul – Haque regime which had tried to limit women to the private sphere with a campaign called ‘Chadar aur Chaardiwari’ meaning ‘The Veil and the Four walls of Home.’ She sang the revolutionary poet, Faiz Ahmed Faiz’s composition to resist the cruel regime. The paper concludes with how these two women artistes redefined music and played a significant role in the preservation and perpetuation of music traditions.