Jimmy Shergill made his debut in Gulzar?s Maachis (1996) as Jimmy. The movie was successful. In Mohabattein (2000), he played a student Karan who is in love with a married woman who does not know if her husband who is with the army will ever return.
He was part of Mere Yaar Ki Shaadi (2002) which was inspired by Hollywood?s My Best Friend?s Wedding. In Dil Vil Pyar Vyar (2002) he played a rich man?s son and was paired with Hrishitaa Bhatt. He was part of the hit comedy Munnabhai MBBS (2003) and Lage Raho Munnabhai (2006).
Many of his movies didn?t do well while some did like Yahaan (2005) and Bas Ek Pal (2006). He was mostly part of multi starrers like Tom Dick and Harry (2006), Yun Hota Toh Kya Hota (2006), Dus Kahaniyaan (2007) and A Wednesday (2008).
He has been quite successful in Punjabi cinema with releases like Yaaran Nal Baharan (2005) and Mannat (2006). In 2009, he will be seen in Munde U.K. De and Tera Mera Ki Rishta.
In Bollywood he has a major release in Karan Johar?s My Name is Khan, in which he plays Shah Rukh Khan?s brother.