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He became the first debutant actor to be cast by Mani Ratnam in the lead role of a film, and revealed that when he found out that he was set to work with the director he was overcome with a "mixture of excitement, awe, fear and expectations".After the success of his first Tamil film, the producers of his previous Kannada film, Shanti Shanti Shanti, dubbed the film into Tamil and released it as Relax, to capitalise on Madhavan's new-found success.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.
During his college years, Madhavan became actively involved in extra-curricular military training and at 22, he was recognised as amongst the leading NCC cadets in Maharashtra, which allowed him to make a trip with seven others as NCC cadets to England.
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.
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.
He also went on to act as a ship's captain in Sea Hawks, as a convict in Yeh Kahan Aa Gaye Hum and worked as a television anchor in Tol Mol Ke Bol amongst other television appearances.