Before acting on the big screen, Chandrachur Singh started out teaching folk music and was later a history teacher at the Doon School. Once an assistant to director Mahesh Bhatt on Awaargi (1990), his first film would have been Jab Pyaar Kiya To Darna Kya opposite Suchitra Krishnamurthy; it was later canned because of financial issues. He lost the male leads in Saudagar (1991) and Bekhudi (1992) but still managed to break through with his debut in ABCL's Tere Mere Sapne (1996) and the National Award-winning Maachis (1996), written and directed by Gulzar. His role as the frustrated youth-turned-terrorist Kripaal got him the Filmfare Award for Best Male Debut.
With that promising start, Singh went on to appear in several multi-hero projects with Daag: The Fire (1999) opposite Sanjay Dutt, Kya Kehna (2000) opposite Saif Ali Khan and Preity Zinta and as the romantic lead opposite Aishwarya Rai in Josh (2000) which also starred Shah Rukh Khan. However, those preceding films became the highlight of his short career. The films that followed were largely unsuccessful and extremely forgettable. Injuries sustained while water-skiing on a trip led to a harrowing surgery and recovery period.
However, in the last few years, Singh can be seen occasionally on television and the big screen. He hosted a weekly food and travel show, Royal Rasoi, on the FoodFood channel in 2012. The show was a good fit for Singh, referencing his own royal connections. That same year, he had a brief role as actor Riz Ahmed's uncle in Mira Nair's The Reluctant Fundamentalist. His last Hindi film which released earlier in 2016, Chal Guru Ho Ja Shuru, was a religious satire that went widely unnoticed.
The new millennium hasn't been too kind on Singh's acting career. He never quite found his groove in his later films and the right role has eluded him since Maachis. There were rumours of him being cast for a part recently in the historical show based on the life of Maharaja Ranjit Singh, but Singh hasn't signed anything new yet. Today, the actor focuses most of his time on music and teaching with intermittent film roles in regional and Hindi cinema.