His score for the Ameer-directed thriller, labelled as 'soul-stirring', fetched him further accolades and eventually yielded a win at the 2006 Cyprus International Film Festival for Best Musical score in a Feature Film, the first such award for an Indian composer. His first of nine album releases of 2005 was Raam. By that time, in a career spanning less than a decade, Yuvan Shankar Raja had established himself as one of the leading and most-sought after music directors in the Tamil film industry, despite having worked predominantly with newcomers and in low-budget productions. The same year, he worked in Vishnuvardhan's debut film Kurumbu, which featured the first remix song in a Tamil film. Furthermore, the film went on to become a blockbuster, cementing the film's lead artist Dhanush and Yuvan Shankar in the Tamil film and music industry. His work in the film, particularly his background score, was unanimously praised, leading to the release of a separate CD consisting of several film score pieces, à la 'Hollywood-style', which was reportedly the first film score CD release in India. In 2003, Selvaraghavan's first independent directorial, the drama-thriller film Kaadhal Kondein released, which is considered a milestone for Yuvan Shankar Raja. At the same time, he made his Telugu debut with Seshu and Malli Malli Chudali and also composed for the Tamil films Junior Senior and Pop Carn, starring Malayalam actors Mammootty and Mohanlal, respectively, though all of which performed poorly at the box office. He then gained notice by churning out 'youthful music' in the college-life based April Maadhathil (2002), the romantic comedy films Kadhal Samrajyam (2002) (The film was never released theatrically, the soundtrack was released in 2002) and Mounam Pesiyadhe (2002), Ameer's directorial debut film, and the triangular love story Punnagai Poove (2002), in which he also made his on-screen debut, appearing in some scenes and one song sequence. This was followed by Bala's Nandha (2001), for which he received rave reviews. The film itself, marking the debut of Selvaraghavan's brother Dhanush, released one year later and became a sleeper hit at the Chennai box office. The soundtrack album of Thulluvadho Ilamai particularly appealed to the younger generation.
The film was directed by Kasthuri Raja, but his son Selvaraghavan wrote the script and worked with Yuvan Shankar Raja for the film's soundtrack album.
In 2001, he had three album releases, the first being Thulluvadho Ilamai, collaborating with Selvaraghavan for the first time. Yuvan Shankar's songs were equally successful, which are considered to have played a major role in the film's great success, while his background score in the film was also well appreciated. Murugadoss's directorial debut in 2000, the action flick Dheena, starring Ajith Kumar, which went on to become a blockbuster and Yuvan Shankar Raja's first major successful film. films, Unakkaga Ellam Unakkaga (1999) and Rishi (2000), he got to work for A. The album would make possible his first breakthrough in the industry and proved to be a major turning point in his career. The soundtrack received a very positive response, being described as 'fresh' and 'different', with a critic from The New Indian Express citing that his 'absolutely enchanting musical score bears testimony to his 'Raja' surname.' The album became very popular, particularly songs such as 'Irava Pagala' and 'Chudithar Aninthu', gaining him first time notice, especially among young people and children. During this time of struggle, he was approached and assigned by director Vasanth to compose the music for his film Poovellam Kettuppar (1999).
The failures of his first projects meant that he was not offered any film projects and assignments subsequently. However, both the soundtrack album as well as the film itself failed to attract audiences and do well, and Yuvan Shankar Raja's following projects Velai (1998) and Kalyana Galatta (1998) were not successful either his compositions for these films did not receive good reviews or responses, with one reviewer labelling the music and background score in the latter as 'cacophony' and 'poor'.