Jassi used to play Harmonium since his childhood. At an early age, he decided to quit studies and learn music. He took his initial music training under Puran Shah Koti and V.S. Jolly. Later he pursued Masters Degree in classical singing from Apeejay College of Fine Arts, Jalandhar. He began his musical journey by participation in musical plays. Initially, he recorded songs for Punjabi movies like Zakhmi and Passport. He released his debut album titled Channa Ve Teri Channani in 1993, but he came to prominence with his 2nd album Dil Le Gayee in 1998. Through this album, he became widely popular in Punjab. His album was a huge hit and was loved by all Punjabi music fans. After this, he released his albums at regular interval and remained in the reckoning.
The motivation for his first hit song Dil le gayi kudi Gujarat ki came from his personal life story. This song helped him gain the limelight, which he always dreamt for. His soundtrack, "Laungda Lashkara" in Hindi movie Patiala House became a huge hit. His song "Ranjha" gave Sufi and Pahari touch. His latest Sufi trance song is ‘'O Laal Ni’', which released in 2016.
In addition to singing, Jasbir Jassi has also acted. He made his acting debut with the Punjabi film 'Khushiyaan' in 2011.This film was the last film in which the ghazal maestro, Jagjit Singh and noted comedian, Vivek Shauq performed.