Rai made her acting debut in Mani Ratnam's Tamil biopic film, Iruvar (1997) with Mohanlal, The controversial film was a critical success and won many awards including Best Film award at the Belgrade International Film Festival, two National Film Awards, and two Filmfare Awards South. Rai appeared in dual roles, opposite veteran actor Mohanlal, with one of her roles being a cinematic depiction of political leader and ex-actress J. Jayalalithaa. Rai made her Bollywood debut in the film, Aur Pyaar Ho Gaya opposite Bobby Deol, which also released that year; the film did not do well at the box office, and was also panned by critics. However, her third project, S. Shankar's Tamil film, Jeans (1998) was a commercial success. The film was also noted for the song "Poovukkul", written by Vairamuthu, and some reviews of the music video compared her to prominent world monuments
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