In 1999, Rai starred in the romantic drama "Hum Dil De Chuke Sanam" which became a significant turning point in her career. 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). Bhansali cast Rai after he met her at the screening of a film and was impressed with her eyes. 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". "Hum Dil De Chuke Sanam" emerged as a major commercial success and won Rai a Filmfare Award for Best Actress.