In 1999, leading Indian director Mani Ratnam selected Madhavan to feature in the leading role of his Tamil romantic film, Alaipayuthey (2000) and the film's subsequent critical and commercial success gave Madhavan his breakthrough as an actor.Portraying the character of Karthik Varadharajan, a young husband experiencing difficulties with his marriage, Madhavan revealed that he studied the technical aspects of film-making from the director and learned the entire script of the film, irrespective of whether he was in the scene or not.He appeared in leading roles in Zee TV's Banegi Apni Baat and Ghar Jamai, while he gained further popularity portraying the character of Shekhar in Saaya.
His first chance in Indian cinema came in the form of Shanti Shanti Shanti (1998), a Kannada film, in which he appeared as a carefree youngster alongside actor Abbas.
However, the film failed to make an impact and went unnoticed at the box office.
His performance as a boorish boxing coach in Irudhi Suttru fetched him Best Actor awards at the Filmfare, IIFA and SIIMA award ceremonies.
He has also worked as a film producer, first making Evano Oruvan with Leukos Films, before setting up Tricolour Films to produce Saala Khadoos (2016).
His younger sister, Devika, is a software engineer settled in the United Kingdom.