Yuvan once confessed that his brother Karthik Raja was more talented than him, but he did not get a successful break into the music business since he did not get a "good team to work with".

[19] T. Siva, the producer of the Tamil language film Aravindhan, after hearing some of the tunes, asked him to compose a trailer music score.

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.

In 2003, Selvaraghavan's first independent directorial, the drama-thriller film Kaadhal Kondein released, which is considered a milestone for Yuvan Shankar Raja.

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 ten-track experimental album, receiving high critical acclaim, was considered Yuvan Shankar Raja's finest work till then and a "musical masterpiece".

[59] Though initially releasing to mixed reviews, with critics doubting whether the songs could attract a modern youth audience,[60][61] his first attempt at rural music turned out to be a major success, following the film's outstanding run at the box office.

The other releases that year include Seeman's Vaazhthugal, Venkat Prabhu's comedy-thriller Saroja, Ajith Kumar's action thriller Aegan and Silambarasan's masala flick Silambattam, out of which, Saroja and Silambattam proved to be successful at the box office, with Yuvan Shankar's score in the former and his songs in the latter garnering accolades and several awards at the 2009 Isaiyaruvi Tamil Music Awards.

[40] In early 2010, he composed his first Bollywood song; "Haq Se", as part of the ensemble soundtrack of the film Striker, starring his close friend Siddharth, which received thoroughly positive reviews.

In 2011, he teamed up with Silambarasan again for the anthology film Vaanam, with the song "Evan Di Unna Pethan" from the album, that was released as a single, gaining popularity.

[79] He went on to work in Venkat Prabhu's action thriller Mankatha, his biggest project till date, and Vishnuvardhan's first Telugu venture Panjaa.

His last two releases of 2011 were the soundtrack albums to the action-masala films Rajapattai and Vettai, both of which received mixed responses and failed to reach success.

In 2013, Yuvan Shankar Raja's music played a significant role in five films, showcasing his ability to blend different styles.

[80] Kedi Billa Killadi Ranga featured upbeat and catchy tracks that were well-received,[81] while Thanga Meenkal highlighted emotional themes, especially through the song "Aanandha Yaazhai".

[84][85][86] Aarambam topped various music charts and strong CD sales, reinforcing Yuvan’s reputation as a leading composer in the Tamil film industry.

Since then, he frequently sang for his father in films such as Anjali (1990), Chatriyan (1990), Thalattu Ketkuthamma (1991), Friends (2001), Kaathal Jaathi (2002), Ramana (2003) and Neethane En Ponvasantham (2012).

Films, featuring some of his most popular songs as a singer, include Thulluvadho Ilamai, April Maadhathil, Pudhupettai, Pattiyal, Azhagai Irukkirai Bayamai Irukkirathu (in which he had sung all songs),[105] Deepavali, Kattradhu Thamizh, Siva Manasula Sakthi, Sarvam, Paiyaa and Naan Mahaan Alla, the latter earning him a Filmfare nomination for the Best Male Playback Singer Award.

According to Yuvan, the show would have featured around 30 songs, sung by well-known singers and his father Ilaiyaraaja, as well as some stage dances in between, by actresses Sana Khan and Meenakshi.

[114] The event, named Yuvan – Live in Concert, which was sponsored, organized and later telecasted on STAR Vijay, was held at the YMCA Grounds, Nandanam, Chennai, on 16 January 2011.

[119] A pre-launch event to promote the concert was held in Brickfields, Kuala Lumpur in the first week of September, where Yuvan Shankar Raja sang a couple of songs.

In 1999, he made the Tamil pop album "The Blast", which contained 12 tracks, featuring vocals by Kamal Haasan, P. Unnikrishnan, Nithyashree Mahadevan, and Yuvan.

Although it didn’t gain mainstream success, it remains a crucial milestone in his career, reflecting his early interest in blending Western and Indian sounds.

In 2010, he joined hands with former President of India A. P. J. Abdul Kalam for a grand music video album titled "Song of Youth".

Rahman for the 2010 World Classical Tamil Conference, the song featured Yuvan Shankar Raja as one of the lead singers among a diverse group of artists.

[135] He also lent his vocals to "Vandhanam" from Karthik Raja’s devotional album Andal, which is where Yuvan sang his very first Carnatic classical song.

The song was produced for the Tamil Nadu government-backed event at the Chennai Formula Racing Circuit, with lyrics penned by Arunraja Kamaraj.

Yuvan Shankar Raja has not learnt Indian classical music,[145] although he has used complex swara patterns and carnatic rāgas in several films, including Nandha and Thulluvadho Ilamai.

[148] Yuvan Shankar Raja has always been a go-to composer for filmmakers like Selvaraghavan,[149][150] Ameer,[151] Vishnuvardhan,[45] Venkat Prabhu,[152] Ram, Lingusamy and Thiagarajan Kumararaja.

Their works brought together Yuvan’s soul-stirring compositions and Muthukumar’s poignant lyrics, creating songs that resonate deeply with fans, even years after their release.

[154] Yuvan Shankar Raja married his girlfriend Sujaya Chandran on 21 March 2005, at the Mayor Sri Ramanathan Chettiyar Hall in Chennai, India.