After completing his bachelor's degree from Indiana University Bloomington, Singh returned to India to pursue an acting career in film. He briefly worked in advertising and made his acting debut in 2010 with a leading role in Yash Raj Films' romantic comedy "Band Baaja Baaraat". The film emerged as a critical and commercial success, earning him the Filmfare Award for Best Male Debut. He gained praise for playing a melancholic thief in the drama "Lootera" (2013), and established himself with his collaborations with Sanjay Leela Bhansali, beginning with the romance "Goliyon Ki Raasleela Ram-Leela" (2013).