Chandrachur Singh is a native of Aligarh, Uttar Pradesh. He attended The Doon School, Dehradun and St. Stephens, New Delhi. He was a music teacher in Doon School before his acting career took off.
Singh has two younger brothers: Aditya Singh and Abhimanyu Singh. He married Avantika Kumari, daughter of Ajai Singh of Glenmoor Cottages, Mcleodganj, Dharamshala. She was educated at the Lawrence School, Sanawar. Their son is named Shraanajai Singh.
Chandrachur Singh made his acting debut in 1996 in the critically acclaimed Maachis for which he won the Filmfare Best Debut Award. Later that year he starred alongside Arshad Warsi in Tere Mere Sapne, which was produced under Amitabh Bachchan Corporation Limited. 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 Josh (2000) opposite Aishwarya Rai and Shah Rukh Khan.
After initial successes, his career went into a low, because of multiple dislocation of his shoulder joint, which he suffered while water skiing in Goa. Because of the pain on his shoulder, he couldn't work out or stay fit which caused him to gain weight and lose roles. His last few releases included Aamdani Atthani Kharcha Rupaiyaa (2001), Bharat Bhagya Vidhata (2002) and the delayed release Sarhad Paar which was shot in 2002 and released in 2006. All three films did average business at the box office.
In 2012, he had a huge comeback with Chaar Din Ki Chandni. The film featured Tusshar Kapoor, Kulraj Randhawa, Anupam Kher, Om Puri and Farida Jalal in lead roles amongst others. Chaar Din Ki Chandni received mixed response from critics, and turned out to be a flop at most places in Box office India. From 2012–present, he has joined Bollywood once again as an actor. He is currently working on his second comeback, titled Zilla Ghaziabad.