Rai made her acting debut in 1997 with Mani Ratnam's Tamil film "Iruvar", a semi-biographical political drama, featuring Mohanlal, Prakash Raj, Tabu and Revathi. The film was a critical success and among other awards, won the Best Film award at the Belgrade International Film Festival. Rai featured as Pushpavalli and Kalpana – dual roles; the latter was a fictionalised portrayal of politician and former actress Jayalalithaa. Her dialogue in the film was dubbed by Tamil actress Rohini. That same year, she was cast as Ashi, a naive teenager in her first Bollywood film – "Aur Pyaar Ho Gaya", a romantic comedy opposite Bobby Deol. Both "Iruvar" and "Aur Pyaar Ho Gaya" were commercial failures and reviewers were critical of Rai's acting ability in both the films. However, for the latter, she won a Screen Award for Best Female Debut.