While in college, Rai did a few modelling jobs. Following appearances in several television commercials, she entered the Miss Indiapageant, in which she placed second. She was then crowned Miss world 1994, after which she began receiving offers to act in film. She made her acting debut in Mani Ratnam’s 1997 Tamil film Iruvar and had her first Hindi film release in Aur pyar ho gaya that same year. Her first commercial success was the Tamil romantic drama Jeans (1998), following which she achieved wider success and won two Best Actress awards at Filmfare for her performances in Hum Dil De Chuke Sanam (1999) and Devdas (2002).