Early career
Rai made her acting debut in Mani Ratnam's Tamil film, Iruvar (1997) with Mohanlal, and was introduced to Bollywood in the film, Aur Pyaar Ho Gaya opposite Bobby Deol, which also released that year; the film didn't do well at the box office. However, her third project, S. Shankar's Tamil film, Jeans (1998) was a critical and commercial success, earning her the Filmfare Best Actress Award South. 
She went on to appear in many Bollywood films. The film, which portrayed Rai in a dual role, took Rai two years to complete. 
A few successful films of her career include Hum Dil De Chuke Sanam (1999), which earned the actress her first Filmfare Best Actress Award and Taal (1999), which gave her another nomination for Best Actress at the Filmfare; 
her performances in both the films were lauded. In 2000, she played a supporting role in the hit films Mohabbatein and Josh. Later that year, she starred in the Tamil film Kandukondain Kandukondain, which won her positive reviews.
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