[3] Similar was the fate of his next film, Thodi Life Thoda Magic (2008) starring Jackie Shroff and Parmeet Sethi.

[5] The same year, he achieved his breakthrough with the romantic comedy-drama Tanu Weds Manu (2011) starring R. Madhavan and Kangana Ranaut in lead roles.

In 2013, he directed the romantic drama Raanjhanaa, starring Dhanush in his Bollywood debut alongside Sonam Kapoor, Abhay Deol and Swara Bhasker in lead roles.

His next directorial was the big-budget romantic drama Zero (2018) starring Shah Rukh Khan, Anushka Sharma and Katrina Kaif in lead roles.

Despite high hype prior to release due to its A-list star-cast and Rai's previous successful ventures, the film emerged as a commercial disaster at the box-office, and received mixed-to-negative reviews from critics.

[12] In 2021, he directed the romantic fantasy comedy-drama Atrangi Re starring Dhanush, Sara Ali Khan and Akshay Kumar in lead roles.