Chandrachur Singh made his acting debut in 1996 in Tere Mere Sapne which was produced under Amitabh Bachchan Corporation Limited.[2] Later that year he starred alongside Tabu in Maachis for which he won the Filmfare Award for Best Male Debut.[4] He appeared in several films which failed to do well but he had success with his lead roles in the multi-starrers Daag: The Fire (1999) opposite Sanjay Dutt, Kya Kehna (2000) opposite Preity Zinta and Saif Ali Khan and Josh (2000) opposite Aishwarya Rai and Shah Rukh Khan.