Jaswinder Singh was born in Mumbai. He is the son of Kuldeep Singh, who composed ghazals such as Tumko dekha to ye khayal aaya and Itni shakti hame dena daata, and wrote music for the movies Saath-Saath and Ankush. He was trained in classical singing by Dr Sushila Pohankar and Pt. Ajay Pohankar, and the classical singer Jagjit Singh

Jaswinder Singh was chosen to sing for the play ‘Kaifi Aur Main’, a epistolary style play dealing with the life and times of the noted lyricist and poet Kaifi Azmi.The play features the husband and wife duo of Javed Akhtar and Shabana Azmi. The lead actors share interesting anecdotes from the life of the great revolutionary poet Kaifi Sahib, while Jaswinder lends his voice to some of the most memorable ghazals and songs penned by Kaifi Saheb.

He performed at Ghalibnaama, a conceptual show based on the prose and poetry of Mirza Ghalib. In July 2012, Jaswinder performed a song “Bahut Yaad Aate Ho Tum” in an episode of Amir Khan’s Satyamev Jayate.