Rahman's 2000 musical Kandukondain Kandukondain directed by Rajiv Menon. He brilliantly portrays the vulnerable and sad Sridhar". Ajith's performance was yet again praised with critics from Rediff, claiming that "Ajith is the real winner", drawing an allusion with the film's script, whilst adding that "it is amazing to see how Ajith has grown as an actor. The film featured dual endings, one with Ajith succeeding in his career, the other with Ajith dejected. The film revolved around the life of a struggling music composer who faces sacrifices to proceed in his career. His next, Mugavaree, won him commercial and critical praise. Amarkalam told the story of a negelected child who grew up and fails to show feelings of love or affection, becoming a gangster in the process, with Ajith's depiction of his rogue character appreciated by critics. His final film before the new millennium was another blockbuster, Amarkalam directed by Saran and featuring Shalini, whom he married shortly after the film. The two following supporting roles in the drama films Anandha Poongatre and Nee Varuvai Ena also brought Ajith plaudits for his portrayals. Furthermore Ajith's portrayal of the brothers was also praised, with critics claiming that the film was an"instant classic" with Ajith showing that he is a "talented actor". The film told the story of a deaf and mute brother setting his eyes on his younger brother's wife, with Ajith's portrayal of the two brothers winning him his first of many awards for Filmfare's Best Actor. Suryaah's thriller, Vaali, which portrayed him in dual roles for the first time opposite Simran, became one of his biggest hits following its release. He debuted in En Veedu En Kanavar (1990) in a minor role as a school student. He had to make a choice between films and racing, and as the films were happening and generating him some money, he began concentrating on it. Following an accident, several business agencies pushed him into modelling for advertisements in print media. He had put a lot of money into racing and would borrow tyres from his friends who used to help when the chains wore out as there was no money in racing at that time.
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Joining as an apprentice, he rose to be a merchandiser with a garment export company, doing small-time press ads and TV commercials occasionally. At 18, Ajith had to take up a job to support his career in racing. During his teens he became fan of Rajnikanth & Kamal Hasan.
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He took up work as a two-wheeler auto mechanic, and got himself a driver's license to coincide with his interests in car and bike racing. He dropped out of Asan Memorial Senior Secondary School in 1986 before completing his higher secondary. He did not speak Tamil as a child, and mastered it only after becoming an actor. Kumar was born to a Sindhi mother from Kolkata and a Keralite father.