She achieved wider success and won two Filmfare Awards for Best Actress for her performances in Sanjay Leela Bhansali's romantic dramas Hum Dil De Chuke Sanam (1999) and Devdas (2002).

"[22] Rai made her acting debut in 1997 with Mani Ratnam's Tamil film Iruvar, a semi-biographical political drama co-starring Mohanlal, Prakash Raj, Tabu and Revathi.

[25][26] In the same year, Rai was cast as a young woman in an arranged marriage set-up, Ashi, opposite Bobby Deol in her first Bollywood film Aur Pyaar Ho Gaya, a romantic comedy.

[29] In the 1998 big-budget Tamil romantic drama Jeans, which S. Shankar directed, Rai appeared alongside Prashanth as Madhumita, a young woman who accompanies her ailing grandmother to the United States to seek medical attention.

[36] The film is an adaptation of Maitreyi Devi's Bengali novel Na Hanyate; it was directed by Sanjay Leela Bhansali, and co-starred Salman Khan and Ajay Devgn.

[39] Rai next took up the leading role of Mansi, a naive young woman with an exceptional singing talent, in Subhash Ghai's musical Taal alongside Akshay Khanna and Anil Kapoor.

[52][55][57] The following year, she starred alongside Govinda and Jackie Shroff in the romantic comedy Albela, which together with her performance, received mostly negative reviews; Taran Adarsh of Bollywood Hungama criticised the film and said Rai is "plastic in some scenes".

[58] After featuring in David Dhawan's slapstick comedy film Hum Kisise Kum Nahin,[59] Rai appeared alongside Shah Rukh Khan and Madhuri Dixit in Sanjay Leela Bhansali's period romantic drama Devdas, an adaptation of Sharat Chandra Chattopadhyay's novel of the same name.

[76][77] After the success of Chokher Bali, Rai returned to mainstream Hindi film in Rajkumar Santoshi's Khakee (2004), an action thriller featuring Amitabh Bachchan, Akshay Kumar, Ajay Devgn and Tusshar Kapoor.

International film critics expressed mixed views on Rai's performance as the Punjabi version of Elizabeth Bennet; a review carried by The New York Times called her "radiantly beautiful but inert"[82] while Rolling Stone noted "she is a world-class hottie with talent to match, as she proves in her first English-speaking role".

[85][87] Derek Elley of Variety called Raincoat a "chamber-sized gem" and said Rai had shunned "her usual immaculate makeup and duds, and looking more like a broken, malfunctioning doll".

[89] Rai next co-starred alongside Sanjay Dutt and Zayed Khan in the 2005 adult drama Shabd, which tells the story of an author who as research for his next book, persuades his wife to pursue a relationship with a younger man.

"[90] In the same year, Rai took on the lead role of Tilo in Paul Mayeda Berges's romantic fantasy film The Mistress of Spices, an adaptation of the eponymous novel by Chitra Banerjee Divakaruni.

[95] Her only successful venture of 2005 was a special appearance in Shaad Ali's crime comedy Bunty Aur Babli, in which she featured in the popular item number "Kajra Re".

[104] In 2007, Rai played the wife of Abhishek Bachchan's character in Mani Ratnam's social drama Guru, which is fictionalised biography of businessman Dhirubhai Ambani.

[105][106] Richard Corliss of Time called Rai's character as an "ornament" but Raja Sen from Rediff.com said she had given "arguably her finest performance, visible especially when she takes over the film's climax.

[109] She next starred alongside Naveen Andrews and Miranda Richardson in Jag Mundhra's independent British drama Provoked as the real-life character Kiranjit Ahluwalia, a non-resident Indian who murders her husband after suffering years of domestic abuse.

[113][114] That same year, Rai Bachchan starred alongside Ben Kingsley, Colin Firth and Thomas Sangster as the Indian warrior Mira in Doug Lefler's epic film The Last Legion.

[120][121] Rai Bachchan's next role was in the 2009 Harald Zwart-directed spy comedy The Pink Panther 2, in which she stars alongside Steve Martin, Jean Reno and Emily Mortimer.

[133][134][135] She then appeared as Mala, an impetuous brat, in Vipul Shah's Action Replayy; a science-fiction comedy co-starring Akshay Kumar, Aditya Roy Kapur and Neha Dhupia.

[139][140] In 2011, Rai Bachchan was cast as the protagonist of Madhur Bhandarkar's social drama Heroine but due to her pregnancy, she was replaced with Kareena Kapoor, the original choice for the role.

[141][142] After a five-year sabbatical from film acting, Rai Bachchan made a comeback with Sanjay Gupta's drama-thriller Jazbaa, co-starring with Shabana Azmi and Irrfan Khan.

[144] The film is a remake of the Korean thriller Seven Days (2007); Rai Bachchan plays Anuradha Verma, a criminal lawyer who is forced to defend a rapist in exchange for her daughter's safety.

Shubha Shetty-Saha of Mid-Day criticised the film's unnecessary and intrusive melodrama, and said Rai Bachchan "looks the part and even does a fairly decent job, barring certain emotional scenes where she clearly goes over the top".

[146] In 2016, Rai Bachchan starred in Omung Kumar's biographical drama Sarbjit, which is based on the life of Indian farmer Sarabjit Singh, who was convicted of terrorism by a Pakistani court and whose sister Dalbir Kaur campaigned for his release.

[155][156] Rai Bachchan's final film role of 2016 was in Karan Johar's musical romantic drama Ae Dil Hai Mushkil, alongside Anushka Sharma and Ranbir Kapoor, in which she plays a poet named Saba.

[187][188] She has modelled for Longines,[189] L'Oréal, Titan Watches,[190] Coca-Cola,[191] Lakmé Cosmetics,[189] Casio pager,[189] Philips,[189] Palmolive,[189] Lux,[189] Fuji films,[189] Nakshatra Diamond Jewellery[192] and Kalyan Jewellers.

[209][210] In September 2012, Rai Bachchan joined the United Nations Secretary General Ban Ki-moon and Hollywood actor Michael Douglas at a ceremony in New York City to commemorate the International Day of Peace.

[236] In 2023, Anjali Belgaumkar of The Indian Express noted despite appearing in around 10 films in a decade, Rai Bachchan still appealed to the younger generation because her impact was not limited to her on-screen roles or fashion choices but there was also an element of "divaness" that made her popular.

[275][276] She was the subject of a 60 Minutes profile on 2 January 2005, which said: "at least according to thousands of Web sites, Internet polls and even Julia Roberts", Rai Bachchan was "the world's most beautiful woman".