While in college, Rai did a few modelling assignments. Following appearances in several television commercials, she entered the Miss India pageant, 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 with the 1997 Tamil film Iruvar and had her first Hindi film release in Aur Pyaar Ho Gaya that same year. Her first commercial success was the Tamil romantic drama Jeans (1998), following which she achieved wider success and two Best Actress awards at Filmfare for her performances in Hum Dil De Chuke Sanam (1999) and Devdas (2002). She garnered critical appreciation for portraying Rabindranath Tagore's heroine, Binodini, in the Bengali film Chokher Bali (2003), a depressed woman in the relationship drama Raincoat (2004) and as Kiranjit Ahluwalia in the British drama film Provoked (2006). Rai's greatest commercial successes have been the adventure film Dhoom 2 (2006), the historical romance Jodhaa Akbar (2008), and the science fiction film Enthiran (2010). She also received praise for portraying a nurse in the drama Guzaarish (2010). Rai took a sabbatical from film acting in 2010, and made her comeback with the thriller Jazbaa (2015).
In 1999, 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] A reviewer for Rediff praised her dancing prowess in it.[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.fter featuring in David Dhawan's slapstick comedy film Hum Kisise Kum Nahin, Rai appeared alongside Shahrukh Khan and Madhuri Dixit in Sanjay Leela Bhansali's love-saga Devdas, an adaptation of Sharat Chandra Chattopadhyay's novel of the same name.[51] She played the role of Paro (Parvati), the love interest of the protagonist (played by Khan). The film was screened at the 2002 Cannes Film Festival and was featured by Time in their listing of the "10 best films of the millennium".[52][53] The film emerged as a major international success with revenues of over ₹530 million (US$7.9 million).[54][55] Alan Morrison, writing for Empire, praised the performances of the three leads and wrote, "Aishwarya Rai proves she has the acting talent to back up her flawless looks".[56] Devdas was chosen as India's official entry for the Academy Award for Best Foreign Language Film and received a nomination at the BAFTA Awards in the Best Foreign Language Film category.[57] In India, the film won 10 Filmfare Awards, including a second Best Actress award for Rai.
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