Cheran initially made breakthrough as a director by making village-based drama films focusing on human relationships, and achieved critical acclaim for his work in Bharathi Kannamma (1997) and Porkkaalam (1997).

He later moved on to work on themes exploring how globalisation affects the Indian middle class, and told the story of scam job offers in Vetri Kodi Kattu (2000) and village-to-city emigration in Pandavar Bhoomi (2001).

Cheran made his directorial debut through Bharathi Kannamma (1997), a village drama narrating the relationship between the daughter of a rich family and their retainer, starring Parthiban and Meena.

The film, which explored the life of a hard-working potter and his poor family, earned Cheran an award for best director from the Tamil Nadu State.

[4] Desiya Geetham (1998) told the story of a Chief Minister being kidnapped and taken to a remote village, and it subsequently met with a controversial response from politicians.

Despite Cheran's intervention and explanation of the script to senior political figures, the film was quickly removed from cinema halls, much to the director's dismay.

[11][12] He later worked again with Parthiban and Murali for the social comedy drama, Vetri Kodi Kattu (2000), which focused on scams committed by agents who promised lavish jobs and salaries abroad, and in the process swindling the money of innocent people.

[13][14] Cheran then made Pandavar Bhoomi (2001) with actors Arunkumar, Shamitha and Rajkiran, which explored themes of wholesale emigration of villagers to the city and the loss of good, solid agricultural lands, culture and solidarity.

[16] Cheran first began work on Autograph in October 2000 with Prabhu Deva and then Vikram cast, though the actors later opted out as a result of schedule clashes.

Autograph told the story of a man named Senthil, presented in four stages of his life – at school, college, work and during his marriage, and Cheran called the film "semi-autobiographical".

The film benefited from positive word-of-mouth and Cheran subsequently increased the number of prints from sixty five to eighty five for the second week, a rarity in Tamil cinema.

[22] Dennis Harvey of Variety wrote it was a "well-mounted production has too much familiar melodrama, and few real highlights (notably one delightful homage to ’70s Tamil musicals), but remains an easy watch".

Mayakannadi was based on the concept of middle class dreams turning sour due to lack of commitment and created attention prior to release owing to Cheran's recent success.

[28] It received mixed reviews and a critic noted "after seeing the film, we hope that the director applies this message in his life by sticking to his core strength of direction rather than dabble in roles that just do not suit him".

[37][38] The period marked a difficult stage for the director, with the lack of directing and acting offers, complemented by family trouble, financial problems owing to C2H, and negative press for controversial statements.

[39] After an extended break, Cheran made a return to direction with the family drama Thirumanam (2019) starring himself alongside Sukanya, Umapathi Ramaiah and Kavya Shetty.

C2H was expected to deliver official original DVDs on the day of a film's theatrical release to homes, for which C2H signed an agreement with DVD maker Moser Baer.

Other films which joined included Thangasamy's Ettuthikkum Madhayaanai, Rohini's Appavin Meesai, Parthi Bhaskar's Arjunan Kadhali, Sashidharan's Vaaraayo Vennilaave, Mahesh Periyasamy's Hockey and Balan's Koditta Idangalai Nirappuga.

[50][40] An arrest warrant was issued by a court against Cheran and his daughter Nivedha, after he did not respond to a bounced cheque following the failure of the venture in March 2016.

He later turned publisher with the Tamil novel Porum Valiyum (War & Pain), a novel on an emotional account of a war-torn Sri Lanka by author Savitri Advithanandhan.

[56] In late 2015, prior to the Nadigar Sangam elections, Cheran publicly criticised the leadership potential and acting ability of actors Vishal and Karthi.

[57] Cheran criticised actor Sharwanand in July 2016 for not cooperating with the promotion of Rajathi Raja, the Telugu version of JK Enum Nanbanin Vaazhkai (2016).

[39] In March 2017, Cheran launched another scathing attack against Vishal and produced a seven-page letter accusing the actor of being "selfish, power hungry and insensitive".