Often cited by the media as the most beautiful woman in the world, Rai made her movie debut in Mani Ratnam's Tamil film Iruvar (1997) and had her first commercial success in the Tamil movie Jeans (1998). She came to the attention of Bollywood in the movie Hum Dil De Chuke Sanam (1999), directed by Sanjay Leela Bhansali. Her performance in the film won her the Filmfare Best Actress Award. In 2002 she appeared in Bhansali's next project, Devdas (2002), for which she won her second Filmfare Best Actress Award.