Hindi films was as an assistant director to S. A. Chandrasekhar in Jai Shiv Shankar (1990) produced by Rajesh Khanna. His final movie with S. A. Chandrasekhar was Nanbargal. In 1993, he made his directional debut through Gentleman. Starring Arjun Sarja in the lead role, the film was made with a higher budget in Tamil cinema during that time, won positive response and became a blockbuster. A. R. Rahman, the film's music composer continued to work with Shankar in his following 6 directorial ventures. His second film Kadhalan, a romantic-action film was released in the following year, had Prabhu Deva in the lead role. In 1996, he collaborated with Kamal Haasan for Indian. It was dubbed in Hindi as Hindustani and Telugu as Bharateeyudu. The film was selected as the country's submission for the Academy Award for Best Foreign Language Film. Following Indian, Shankar began work on Jeans, which released in 1998 and became the most expensive film in Indian cinema at that time with a budget of 200 million. Upon release, it became one of the highest grossing Tamil films of the 1990s. He made his production debut through Mudhalvan (1999). Arjun Sarja joined the project. 2000s Shankar opted to remake Mudhalvan in Hindi as Nayak, thus making his Bollywood debut. Nayak, released in September 2001, was declared a "Flop" by Box Office India due to the poor marketing, its high budget and distribution price. It went on to gain a cult status despite not doing well at the box office. Shankar started to work on his next film which was supposed to be a science fiction film titled Robot that was slated to have Kamal Haasan in the lead, the project was stalled since Kamal Haasan was busy with other projects. Later, the project could not move forward due to budgeting problems. His musical entertainer film Boys was released in 2003, which received mixed response from the critics and audience, prompting it to do only average business. However A. R. Rahman's soundtrack for the film became a major sensation. On the box-office front, the Telugu dubbed version of Boys was a big hit in Andhra Pradesh. His psychological thriller Anniyan, featuring Vikram in three distinct characters (Ambi, Remo & Anniyan) was released in 2005 with Harris Jayaraj as the composer for his film. Anniyan turned out to become the second highest grossing Tamil film of 2005. Shortly after