His film Anbanavan Asaradhavan Adangadhavan was panned by critics and was commercially unsuccessful. In 2017, it was reported that Silambarasan had signed up for an English-language film. His next film Achcham Yenbadhu Madamaiyada was his second collaboration with Gautham Menon and A. In 2016, Silambarasan starred in the Pandiraj-directed Idhu Namma Aalu alongside Nayanthara, Andrea Jeremiah and Soori playing lead roles. After a sabbatical of three years, he acted in Vaalu, which was released on 14 August 2015. Later that year, his next release was Osthe (2011) in which Silambarasan played a police officer. Malathi Rangarajan from The Hindu called it a significant film in his career. In early 2011, he appeared in the multi-starrer Vaanam (2011) as Cable Raja, a poor youngster. The following year he appeared in two films. Balachander in an open letter called Silambarasan's performance as his best in his career. In 2010, his film Vinnaithaandi Varuvaayaa, directed and written by Gautham Menon, became a Tamil 'cult classic' film. Later that year, he appeared in another action masala film Silambattam. In 2008, he starred in the action masala film Kaalai, which was a flop. He next starred in and directed Vallavan (2006), as well as writing its story, screenplay and co-dialogue. This was the second time that Simbu and Jyothika worked together after the success of Manmadhan (2004). In 2006, he starred in Saravana, directed by K. This movie was described by the critics as realistic. In Thotti Jaya, Silambarasan played the role of an orphaned gangster who finds love. His final release in 2004 was Manmadhan, co-starring with Jyothika for the first time. Divya Spandana, played his Love interest. After this, Silambarasan acted in a movie called Kuththu, a remake of the Telugu film Dil.

Sonia Agarwal paired with him as his lady love. This film, which deals with the relationship between a Hindu boy and a Christian girl, Simbhu was praised due to his 'restraint and matured' performance. His release, in 2003, Alai, which marked the first collaboration of Simbu and Trisha. His second film was Dum (2003), which was loosely based on Jagannadh's 2002 Kannada film Appu. Silambarasan played his first protagonist role in Kadhal Azhivathillai (2002), directed by his father. In Samsara Sangeetham, Silambarasan danced to a song singing 'I am a Little Star, Aaaven Naan Super Star'. He then started acting in his father's movies from 1995, including Thai Thangai Paasam, Oru Vasantha Geetham, En Thangai Kalyani, Enga Veetu Velan, Monisha En Monalisa, Oru Thayin Sabhatham, Samsara Sangeetham, Shanti Enathu Shanti, Pettredutha Pillai, Thiruvalla and Sabash Babu. Silambarasan appeared as a new born baby in the film Uravai Kaatha Kili held by his father T Rajendar. Main article: Silambarasan filmography 1995–2001

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