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Jai carried on featuring as the lead actor, as opposed to multi-starrer films, between 2014 and 2016 albeit to limited success. His first release in the period, the comedy film Vadacurry (2014) opened to positive reviews from critics and performed well at the box office, with a critic noting: "Jai is good with romance and comedy, so the role is perfect for him". His subsequent releases including Aascar Films' romantic-comedy Thirumanam Ennum Nikkah (2014) alongside Nazriya and Valiyavan (2015), co-starring Andrea Jeremiah, where the former performed average and the latter performed poorly at the box office, while also receiving negative reviews. Likewise, his two releases in 2016, Manimaran's social drama Pughazh (2016) and Gautham Menon's long-delayed production Tamilselvanum Thaniyar Anjalum (2016), where he portrayed a mail carrier, also performed average at the box office. During the period, producer T. Siva spoke out against Jai for failing to promote his films despite his lack of stardom. Following a string of unsuccessful films, Jai experienced critical and commercial acclaim with his role in Venkat Prabhu's sequel Chennai 600028 II (2016), where he reprised his role of Raghu from the original film. The story revolved around the reunion of the old cricket team for the wedding of Jai's character, and opened to positive reviews in December 2016, with critics stating that Jai made "a good comeback". In 2017, Jai appeared in the romantic comedy film Enakku Vaaitha Adimaigal, portraying an IT worker who is unlucky in love. In late 2018, he signed Madhura Raja alongside Mammootty marking his debut in Malayalam Cinema which was release in April 2019. Then next, Neeya 2 (2019), a horror film. His 25th film, Capmaari was directed by S. A. Chandrasekhar.

Jai is also a car racer. "Crazy about racing" since his childhood, he said he was inspired by Tamil actor Ajith Kumar to get into racing. In June 2014, he participated in his first car racing tournament, the JK Tyre National Racing Championship at the Irungattukottai Race Track in Sriperumbudur, Chennai.

Jai was arrested for allegedly driving a car under the influence of alcohol and hitting a divider in Adyar. Sources said the actor was booked in 2014 after his vehicle rammed a median near Kasi Theatre. The police have recommended the cancellation of his license.

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. The film opened to mixed reviews and became an average grosser at the box office, with critics noting that Jai was "disappointing" and that he "hams it up".

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. Portraying a timid working class professional, his role was well received and the film performed well at the box office. 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". Jai then accepted to play a secondary role in Atlee's Raja Rani (2013), and admitted he was initially apprehensive about accepting the offer, only choosing to do so after being convinced by the film's climax. He mentioned that he wanted to portray a memorable guest role like that of Karthik in Mani Ratnam's Mouna Raagam, and worked hard to get into the skin of his character, Surya, taking close to ten takes in certain scenes.

Jai subsequently garnered 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. He was introduced as Debut singer in the movie Jarugandi (2018).

He was then seen in Venkat Prabhu's romantic comedy Goa (2010), where he played a villager on a coming-of-age trip to Goa alongside Vaibhav Reddy and Premgi Amaren. Jai's temporary ban from films had delayed the project and he once again grew a beard to portray his character of Ramarajan. Despite positive hype surrounding the film prior to release, it only won average reviews and collections at the box office. 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. He shed weight to sport the school boy look and later added weight and muscle to look a matured man in his late twenties for the film. 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. Similarly, his performance in the romantic film Kanimozhi was described "as endearingly likeable" and that "he had come out with a natural performance", but the film failed commercially. Discussing his five consecutive failure films, Jai admitted that during that period in his career, he had chosen to feature in films without considering the true scope of its potential success, only to avoid a long gap between releases. Since then, he has actively chosen to associate himself with big banner films rather than ventures by debut production houses in order to ensure that his films are well publicized prior to release.

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. The actor, who was filming for Vaamanan, Aval Peyar Thamizharasi, Adhe Neram Adhe Idam and Arjunan Kadhali at the time, revealed that only Vaamanan would do well and the rest would become financial failures. The producer of his films also revealed they wanted to take action against Jai for "making such irresponsible and damaging statements about his own films." 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. The film's producer, Soundarya Rajinikanth, intervened and bailed Jai out of the ban. 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". The film did not replicate the commercial success of his previous ventures, though his performance was described as "commendable". Meanwhile, Adhe Neram Adhe Idam opened to unanimous negative reviews, with a reviewer noting that Jai "with his sleepy eyes looks like he really doesn't want to be in this film at all".

Jai Sampath, known mononymously as Jai, is an Indian actor working in Tamil films. The nephew of music composer Deva, Jai had worked as a keyboardist in films and had made his acting debut in a supporting role in Bagavathi (2002). In 2007, he successfully auditioned for a leading role in Venkat Prabhu's sports film Chennai 600028.

Jai made his film debut at age 16 as Vijay's younger brother in the 2002 film Bhagavathi, with director A. Venkatesh choosing Jai as a result of his striking similarity in appearance to Vijay. Jai was then set to make his debut in a lead role in a remake of the Telugu film 6 Teens, but the film never took off, as well as Nambiraj's Touch did not. 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. He instead chose to concentrate on a career in music, often working for Deva's films a keyboardist alongside his cousins, music composers Srikanth Deva and Bobo Shashi.