Her debut movie was in the Tamil industry that was directed by Mani Ratnam titled Iruvar. Even in her debut movie she has handled dual roles along with Mohanlal and Tabu. Aur Pyaar Ho Gaya was her first movie in Bollywood. Jeans was her third project with director Shankar and the movie made her to be identified in the industry as a good actress.
In 1999, she starred in Sanjay Leela Bhansali's Hum Dil De Chuke Sanam opposite Salman Khan and Ajay Devgan. The film was centered around Rai's character, Nandini, who is forced to marry Devgan's character despite being in love with another man (Khan), and as her husband tries to get her to her previous love, she eventually falls for him. Rai's portrayal won her critical acclaim, and the film became her first box office success in Bollywood. She won her first Filmfare Best Actress Award for the film. In the same year she appeared in Subhash Ghai's Taal, in which she played the role of a young village girl 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.
In 2000, she appeared in Mansoor Khan's Josh alongside Shahrukh Khan and Chandrachur Singh, in which she played a Catholic girl named Shirley who falls in love with the sibling of her Brother's enemy. The film was a commercial success. Later that year she appeared in Satish Kaushik's Hamara Dil Aapke Paas Hai opposite Anil Kapoor. It was a moderate success and her performance earned her a Filmfare Best Actress Award nomination. Later that year she played a supporting role in the Aditya Chopra's Mohabbatein alongside Amitabh Bachchan and Shahrukh Khan, the film was a major commercial success and became the second highest grosser of the year, it also earned her a Filmfare Best Supporting Actress Award nomination. Later that year, she also starred in the Tamil film Kandukondain Kandukondain, alongside Mammooty, Ajith Kumar and Tabu.
In 2002, she appeared alongside Shahrukh Khan and Madhuri Dixit in Sanjay Leela Bhansali's Devdas, an adaptation of Sharat Chandra Chattopadhyay famous novel by the same name.
In 2003, she acted in Rituparno Ghosh's Bengali film, Chokher Bali, an adaptation of one of Rabindranath Tagore's novels by the same name. She portrayed the character of a young woman called Binodini, who is left to her own devices when her sickly husband dies soon after they are married.
In 2004 she appeared in Gurinder Chadha's Bollywood-style English adaptation of Pride and Prejudice by Jane Austen, Bride and Prejudice alongside Martin Henderson. In the film she portrayed the role of Lalita Bakshi, the film's counterpart of Elizabeth Bennet in Austen's novel. This was followed by Rajkumar Santoshi's Khakee alongside Amitabh Bachchan, Akshay Kumar, Ajay Devgan and Jayapradha, in the film she played a negative role for the first time in her career. In the same year she appeared in in her second film with Rituparno Ghosh, Raincoat alongside Ajay Devgan. The film was highly acclaimed by the critics, whereas she received rave reviews for her performance.
In 2005 she appeared in Shabd a film based on a love triangle alongside Sanjay Dutt and Zayed Khan. The film was a box office flop wheraeas it received average reviews from the critics. Her next release that year was Paul Mayeda Berges's The Mistress of Spices based upon the novel The Mistress of Spices by Chitra Banerjee Divakaruni in which she starred alongside Dylan McDermott. The film received negative review by critics and was also a commercial failure.
In the year 2006, she starred in J P Dutta's Umrao Jaan, a second film adaptation of the Urdu novel Umrao Jaan Ada (1905), written by Mirza Hadi Ruswa. She portrayed courtesan and poetess by the same name from 19th century.
In 2007 she appeared in Mani Ratnam's Guru as Sujata, speculated to be based on the life of Indian businessman Dhirubhai Ambani, it was a rag to riches story about an ambitious small town man who ends up as the owner of the biggest corporation in India. The film was premièred at the Elgin Theatre in Toronto, Ontario, Canada, making it the first Indian film to have a mainstream international premiere in Canada.
In 2008, she starred alongside Hrithik Roshan in Ashutosh Gowariker's historical drama Jodhaa Akbar playing the role of Jodha Bai, the Hindu wife of the Muslim Mughal emperor Jalaluddin Muhammad Akbar, played by Roshan. The film was a critical and commercial success, becoming one of the highest Bollywood grossers that year. She earned her eighth nomination for Best Actress at the Filmfare for her performance.
In 2009 she was awarded the Padma Shri for her contributions to Indian cinema. In the same year she refused to accept the second-highest Order Of France, Ordre des Arts et des Lettres as her father was suffering from serious illness, and she wanted her whole family to attend the award function. She is only the fourth Indian actress after Amitabh Bachchan, Nandita Das and Shahrukh Khan to be chosen for an Order Of France. At the same year also she was starring in the English film The Pink Panther 2 as Sonia Solandres.
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