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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.
Madhavan was auditioned for the leading role of Tamizhselvan amongst several other more established actors, but Mani Ratnam eventually left him out of the project citing that he thought his "eyes looked too young" for a senior role.
As his film career failed to take off, Madhavan went on to feature in Hindi television serials, appearing as a crook in his first venture Yule Love Stories.
Featuring a popular soundtrack by Harris Jayaraj and marketed as a Valentine's Day release, Minnale further built on the actor's image as a romantic hero and was later listed as a "classic romantic film" from the Tamil film industry.