Jai subsequently garnered more praise for diverse roles, including a villager on holiday in Goa (2010), a timid factory worker in Engaeyum Eppothum (2011) and a customer care executive in the romantic drama Raja Rani (2013), which became his biggest commercial successful film.

[4] Born into a family of musicians, Jai has stated that music was close to his heart and that it influenced him in his "growing years", particularly crediting his uncle, the composer Deva.

[10][11][12] Several other offers came his way including roles in Alai (2003) and Devathayai Kanden (2005), but Jai was insistent that he earn his place in the film, rather than being chosen on the basis that he was music composer Deva's nephew.

His friend, the singer Yugendran, recommended Jai to audition for a role in Venkat Prabhu's directorial debut Chennai 600028 (2007), based on gully cricket.

[14] In March 2009, Jai ran into trouble for making controversial comments about the potential box office fare of his future films that he had signed in that period.

"[18] Initially, the Nadigar Sangam council had asked him to complete his pending assignments before he could start work on any other project, beginning with Venkat Prabhu's Goa.

[19] His next release Ahmed's Vaamanan (2009), an action thriller featuring Priya Anand, Lakshmi Rai and Rahman, marked his first commercial role with a critic noting: "from swift stunts to rapid dance movements, Jai has got it all".

He appeared in Aval Peyar Thamizharasi with different looks throughout the film to reflect his character's growth, with the main ones being that of an eighteen-year-old boy and a twenty-eight-year-old man.

[22] Critics lauded Jai's performance, citing: "he shows that he is in the process of grooming himself to become a well-rounded actor" and "that he can bring in complex emotions on his face at the drop of a hat", but the film did not fare well at the box office.

[8] After his string of failures, Jai signed up to play a role in AR Murugadoss's debut production Engaeyum Eppothum (2011), after being impressed by Saravanan's script.

A critic noted: "the highlight of the film is its lead actors Anjali, Ananya, Jai and Sharwanand who live the role of the characters they play".

[8] His second release of the year was the fantasy comedy Naveena Saraswathi Sabatham (2013), where Jai played a Siddha doctor who becomes deserted on an island after a bachelor party with his three friends.

[29][30] Likewise, his two releases in 2016, Manimaran's social drama Pughazh (2016) and Gautham Vasudev Menon's long-delayed production Tamilselvanum Thaniyar Anjalum (2016), where he portrayed a mail carrier, also performed average at the box office.