Shergill was born in a Sikh family in Deokahia village, Sardarnagar, Gorakhpur district, Uttar Pradesh. He hails from a family of land owners and distillers, and his paternal grandaunt was the famous Indian painter Amrita Sher-Gil.
He studied at St. Francis' College, Lucknow for a few years and then moved to Punjab, the place of his ancestors, in 1985. He studied at The Punjab Public School, Nabha and at Bikram College, Punjabi University, Patiala.
He went to Mumbai after a cousin convinced him to try his luck in the film industry. There, he attended Roshan Taneja's acting classes.
Jimmy Shergill started his acting carrer with Maachis, which was a critically acclaimed film and did reasonably well at the box-office. The actor has been well appreciated for his performances in Yahaan, A Wednesday and Tanu Weds Manu.