[3] Singh began his career in Bollywood working as an assistant director before directing his first feature film Raqeeb (2007).

Jatt and Juliet series and Punjab 1984 rank among the most successful films of Punjabi cinema, both commercially and critically.

Singh followed this up with 2009 directed Dil Bole Hadippa!, a sports comedy in which Rani Mukerji disguises herself as a man to join an all men's cricket team.

[9] Singh began working in Punjabi cinema and directed his debut film Yaar Annmulle with actor Arya Babbar in the lead role.

The coming of age comedy film emerged as a breakout project for Singh as it was declared a 'hit' by Box Office India.

[10][11] Starring Diljit Dosanjh and Neeru Bajwa, it followed the rivalry and eventual friendship of the two characters played by the pair of actors, while navigating foreign life.

[12][13] Following the success of Jatt & Juliet, he worked exclusively with Diljit Dosanjh in several films in the Punjabi language, which achieved record-breaking success, including the comedies Jatt & Juliet 2 (2013) and Disco Singh (2014),[14][15] the period drama Punjab 1984 (2014),[16] and the superhero comedy Super Singh (2017).

[19] Singh made his return to Bollywood with the 2019 war film Kesari, which is based on the historic Battle of Saragarhi.

[20] The film featured Akshay Kumar and Parineeti Chopra in the lead roles, supported by an ensemble cast, and was co-produced by Karan Johar and Zee Studios.