In Ooty, unknown men (Arjun & Goundamani) perform a swashbuckling heist of money of several crores while being in disguise diverting the attention of police, and escape in Nilgiri toy train, much to the frustration of a chasing police officer Ratnam (Ajay Rathnam).
Meanwhile, in Chennai, Krishnamoorthy alias Kicha (Arjun) is a respected citizen who runs a home-based appalam business along with Mani (Goundamani). Susheela (Madhoo), one of Kicha's many female employees, has a crush on Kicha and is constantly demanding his attention. Adding to her woes, the arrival of her jovial cousin Sugandhi (Subhashri), who makes the place so lively and playful with silly fights between Mani and Babloo (Senthil). Sugandhi later develops a crush on Kicha, especially after being saved by him from some molesting goons. But Kicha reveals to her that he has no such feelings for her and wants her to find a suitable mate. Before leaving Chennai, Sugandhi steals Kicha's ring as a souvenir.
After several unsuccessful attempts at nabbing the thief, a disgraced Azhagar Nambi (Charan Raj) shaves his head and left with a ring mark on his face, after a scuffle with the thief. On investigating, he later realises that the mark was formed by a ceremonial ring worn by Brahmin priests, but to his vain finds that the specific design of this ring is uncommon to Brahmin priests, but rather resembles a mangalsutra. Both intrigued and frustrated, Nambi is forced by his parents into getting married and by coincidence to Sugandhi, from whom he gets the particular ring he was tracking and finds out that it belongs to Kicha.
In an attempt to trap and arrest Kicha, Nambi plots an attempt at Kicha's house where they were invited for wedding diner, hosted by Kicha, where he shoots Kicha, but the latter narrowly escapes with bullet injury in his hand, along with Mani. They were followed by Susheela to their hideout, where Susheela finds the duo, and fabercasts Kicha for his false deed.
Then, Kicha reveals his flashback about his student life as a district level topper along with his best friend Ramesh (Vineeth), and even then they both were denied their desired Medical college seats due to bribery, that leads to tragic suicides of his mother Ponnamal (Manorama) and Ramesh, and since then, he became a thief to build a college of his own, where he desires to make education available to the deserved, with out any difference to poor, rich, or any caste.
In order to fund the final stages of the college building, aware of the police trap, Kicha makes one last attempt to steal money from the Chief Minister (Rajan P. Dev) resulting successfully, but Nambi gains the upper hand in arresting him. In the courtroom, Kicha demands the Chief minister of the state should come to the court room, who was the then educational minister who demanded the bribe from him. Though the Chief Minister is exposed to the public, he is still let off, which infuriates a youth who aspired by the ideologies of Kicha kills the minister planting a bomb on himself. During the end credits, it is shown that Kicha serves his sentence in jail and he subsequently inaugurate the medical college for the poor students, after his release from jail.Arjun as Krishnamoorthy (Kicha)Madhoo as Susheela (Susi)Goundamani as ManiCharan Raj as Azhagar NambiSubhashri as SugandhiSenthil as BablooVineeth as RameshManorama as Ponnammal, Kicha's motherM. N. Nambiar as Ramesh's fatherRajan P. Dev as CMAjay Rathnam as RatnamPrasanna as LawyerOmakuchi NarasimhanChokkalinga BhagavatharRajendran as Stunt artist
Special appearances in "Chikku Bukku Rayile" songPrabhu DevaGouthami TadimallaRaju SundaramRaghava Lawrence
The film marked the directorial debut of Director Shankar, former assistant of S. A. Chandrasekhar who went to become one of the best directors in Indian cinema.
Sarathkumar was initially approached for the lead role but since he was busy with other projects he was replaced by Arjun.
The score and soundtrack of the movie was composed by A. R. Rahman and lyrics penned by Vairamuthu and Vaali. The soundtrack became a chartbuster upon release and was highly acclaimed. Gentleman marked the beginning of a famed collaboration between A. R. Rahman and director S. Shankar. The film and soundtrack were dubbed and released in Telugu with the same name. The lyrics were penned by Rajashri for this version.
The choreography was done by Prabhu Deva who also made an appearance in the song "Chikku Bukku Rayile" written by Vaali.
The acclaimed soundtrack earned A. R. Rahman, his second Filmfare Best Music Director Award of the year 1993. He also won the Tamil Nadu State Film Award for Best Music Director for his work. Sujatha got the Tamil Nadu State Film Award for Best Female Playback for her soulful rendition of the track "En Veettu Thotathil".
A Gentleman instrumental adaptation album was subsequently released on Lahari and became a run away success. The track "Ottagathai Kattiko" soundtracked a BBC fashion show. The song is based on Carnatic rāgam Dharmavati.41st Filmfare Awards SouthBest Film - K. T. KunjumonBest Director - ShankarBest Music Director - A. R. Rahman1993 Tamil Nadu State Film AwardsBest Actor - Arjun SarjaBest Director - ShankarBest Music Director - A. R. RahmanBest Female Playback Singer - Sujatha - "En Veetu Thotathil"