In 1999,Aishwarya Rai starred in the romantic drama Hum Dil De Chuke Sanam which became a significant turning point in her career.[32] The film, an adaptation of Maitreyi Devi's Bengali novel Na Hanyate, was directed by Sanjay Leela Bhansali and co-starred Salman Khan and Ajay Devgan. She played the main protagonist Nandini, a Gujarati woman who is forced into wedlock (with Devgan's character) despite being in love with another man (played by Khan). TheMovieReport.com praised Rai's performance over her co-actors and noted, "Rai, in a luminous, award-winning performance (largely considered her big dramatic breakthrough—and justifiably so), fills in the conflicted emotional shades that Khan fails to bring with his one-dimensional presence".[33] Hum Dil De Chuke Sanam emerged as a major commercial success and won Rai a Filmfare Award for Best Actress.[34] Rai next took the leading role of Mansi, an aspiring singer, in Subhash Ghai's musical Taal; alongside Akshay Khanna, Anil Kapoor, Amrish Puri and Alok Nath.[35] Rai's performance earned positive feedback from critics. Rediff noted "After being praised for her looks and acting talent in Hum Dil De Chuke Sanam, Aishwarya has excelled in Taal. The film will again enhance her reputation as an actress; besides acting well she also dances beautifully.[36] A moderate domestic success, Taal was notable for being the first Indian film to feature in the top twenty listing at the American box-office.[37][38] Rai received a second Best Actress nomination that year at the Filmfare Awards ceremony.
In 2000, Rai starred in Kandukondain Kandukondain, a Tamil language adaptation of Jane Austen's novel Sense and Sensibility. Directed by Rajiv Menon, the film also starred Tabu, Mammooty and Ajith Kumar in prominent roles. Rai was cast as Meenakshi (based on the character of Marianne Dashwood), the younger sister of Tabu's character.[39] The film was a critical and commercial success and earned Rai positive comments from critics; a review carried by The Indian Express summarised, "Attacking her role with just the perfect dollop of innocence, Aishwarya does full justice to her part, and matches up perfectly to Tabu."[40][41][42]
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