In 1999 Rai starred in Sanjay Leela Bhansali's Hum Dil De Chuke Sanam opposite Salman Khan and Ajay Devgan. The film was centered on Rai's character, Nandini, who is forced to marry Devgan's character despite being in love with another man (Khan). As her husband tries to get her to her previous love, she eventually falls for him. Rai's portrayal won her critical acclaim, with a review on Rediff.com writing, "Aishwarya looks beautiful as usual ... This film will most likely draw her accolades from all over, maybe even get her recognised as an actress the way Manisha Koirala did in Khamoshi. In many scenes, there is no trace of makeup and she looks very fresh". The film became her first box office success in Bollywood and earned her first Filmfare Best Actress Award for her.
In the same year she appeared in Subhash Ghai's Taal, in which she played the role of a young village woman, Mansi, who becomes a big pop star after being hurt by her lover played by Akshay Khanna. The film was an average performer in India but was a big success among the international audience, especially in the United States, where it became the first Indian film to reach the top 20 on Variety's box office list. Her performance in the film was praised with Rediff.com writing, "After being praised for her looks and acting talent in Hum Dil De Chuke Sanam, Aishwarya has excelled in Taal. She looks ethereal and unlike the former film, has a very sober and soft role. Though she looks pained and tragic in most of the film, she does a good job of a woman who is very protective of her father and one who doesn't think twice before rejecting a lover who has insulted her father." She received another Best Actress nomination at the Filmfare for her performance in the film
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