After completing his college, Shergill formed a band named Kaffir. The band played in some competitions and college festivals before parting ways. Shergill initially composed
jingles for advertisement agencies such as
Yamaha RX-T motorbikes and Times FM. In October 2008, Shergill released his second album
Avengi Ja Nahin under YRF Music. The album contains nine songs and deals with issues like communal violence, like the
Bilkis Bano case expressing social responsibility and the need for "collective morality". He also appeared in
MTV Unplugged (India) in 2011. He lent his voice to Yash Chopra's 2012 romantic film
Jab Tak Hai Jaan singing the leading number "Challa" composed by
A. R. Rahman and the lyrics penned by
Gulzar. In March 2012, he released his third album
III. Rabbi Shergill has been critical of current Punjabi singers who have taken Punjabi music and identity to the global stages such as
Diljit Dosanjh., Shergill's major gripe being his generalization of popular Punjabi music as being Narcissist . While Shergill has had ardent fans himself, there are many who disagree with this generalization and instead blame it on Rabbi's unrevivable career lost because of his transition to Bollywood. Rabbi Shergill has also been critical of world recognized two time winner and five time nominee of the Academy Award (Oscar)
A.R. Rahman. in a recent podcast where Shergill accused Rahman of ruining Bollywood music mostly due to poor lyrics, which are perhaps because of translation losses that happen with regional music in India. ==Musical style==