The production began with Vasanth being selected as director who later opted out due to personal reasons. Suresh Krishna replaced him to direct thus marked his first collaboration with Rajinikanth. Principal photography of the film began at AVM Studios and the filming held at various places. The score and soundtrack was composed by Deva and lyrics for all songs were written by Vairamuthu. The cinematography was handled by P. S. Prakash and editing was handled by the duo Ganesh Kumar. The dialogues for the film were written by Shanmugasundaram.
Annamalai (Rajinikanth) is a milkman, while Ashok (Sarath Babu) is the owner of a five star hotel in Chennai. They both are very close friends from childhood days. But Ashok’s father (Radha Ravi) does not like his son’s friendship with a poor milkman. Annamalai is kind-hearted and is innocent. He falls in love with Subbu (Kushboo). Ashok falls in love with a poor girl Shanthi (Rekha) and Annamalai arranges Ashok and Shanthi’s wedding. This angers Ashok's father as he thinks Shanthi does not have the status to become his daughter in law.
Annamalai encounters a problem with Ekambaram (Vinu Chakravarthy) following which Ekambaram understands Annamalai’s good nature. Annamalai’s small home along with a few cents of empty land is located in prime location and Radharavi pressurizes Ashok to buy that land so that they can construct one more star hotel. Ashok initially hesitates as he does not want to mix business and friendship, but later agrees and asks Annamalai with hesitation. But Annamalai happily accepts and also agrees to give the land for free of cost. Ashok feels proud of Annamalai and informs his father that Annamalai has to be made a shareholder in the new hotel. Ashok's father agrees but decides to cheat Annamalai and gets sign in empty papers.
The star hotel is constructed and Ashok's father plans to demolish Annamalai’s home which is located next to the hotel. Also, Ashok's father and Ashok's cousin Sarkunam (Nizhalgal Ravi), forge documents and take control of Annamalai’s empty land. Annamalai learns of this plan and picks up quarrel with Ashok's father. Ashok interrupts and he misunderstands Annamalai without knowing the truth for fighting with Ashok's father. Ashok gets angry and demolishes Annamalai’s home which is in the remembrance of Annamalai’s father. Annamalai gets shocked seeing Ashok’s activities and challenges that he will also become rich and take revenge on Ashok.
Ekambaram helps Annamalai to secure funds and he starts a small sweet business and over a few years he becomes so rich and he also builds a star hotel in Chennai which becomes more popular than Ashok’s hotel. Sarkunam steals money from Ashok and knowing this, Ashok asks him to leave. Sarkunam joins Annamalai’s hotel and also gets married to Annamalai’s sister, Vaishnavi. Annamalai wins Ashok and become the president of hotels association and Ashok also faces financial troubles. Annamalai’s daughter and Ashok’s son are college-mates and love each other, much to Annamalai's anger. Ashok and Annamalai appear for a public auction and the auction price keeps increasing. Ashok wins the auction for Rs.12 Crores despite his father asking him not to quote such a huge amount as this was a trick played by Annamalai to increase the price.
Ashok has no money to pay for the auction and is forced to sell his bungalow to get money. Annamalai purchases Ashok’s bungalow thereby winning the challenge made years ago. But Annamalai gives the registration document to his mother (Manorama) and asks her to handover to Ashok itself as he does not want to punish his friend. Ashok and his father realizes their mistake and apologise to Manorama knowing Annamalai's kind heart. Annamalai also gets to know that it was only Radharavi and Sarkunam who forged the documents and Ashok was unaware of the his father’s plans. In the meantime Sarkunam tries to kill both Ashok and Annamalai and try to take Annamalai’s properties. But Ashok and Annamalai fight together and Sarkunam realises his mistake. Annamalai and Ashok finally join together and become best friends again.Rajinikanth as Annamalai
Sarath Babu as Ashok
Kushboo as Subbalakshmi a.k.a. Subbu
Janagaraj as Panchachalam (Panchu)
Radha Ravi as Ashok's Father
Nizhalgal Ravi as Sarkunam
Vinu Chakravarthy as S. Ekambaram (MLA and minister)
Manorama as Annamalai`s mother
Vaishnavi as Annamalai's Sister
Rekha as Shanthi
Karan as Ashok's son
V. Subramanian as The Minister
Vishnukanth as Junior Ashok
Dakshayini as Annamalai's daughter
Originally, Kavithalaya Productions had chosen Visu as the director of Annamalai. But due to some contradiction with Rajinikanth, he opted out and they hired Vasanth. Due to "personal reasons", Vasanth too left and Suresh Krissna was later finalized for the director's part, after K. Balachandar had requested him to do so.
When Suresh Krissna came on board the script wasn't complete and the shooting started in a hurry as the film release date had already been fixed as on June 27, 1992. Suresh recalled that Shanmugasundaram, the film's dialogue writer narrated him the one liner of the plot, Suresh felt that detailing should be done to the script to which Shanmugasundaram assured that it can be done during the shoot.
When the title of the film was announced as Annamalai, few people has misgivings about the title as it would create a negative connation. Balachander and Rajinikanth had decided on the title and refused to change it. Annamalai was launched at AVM Studios at the venue of Pillaiyar temple. The film's Muhurat shot was held in a set of a court room, it was a comedy scene where Rajini would save Sarathbabu from a criminal offence. Suresh removed the scene from the film as he felt that this scene had no bearing on the script.
Radharavi revealed that he wasn't interested to play elderly characters but agreed to appear in Annamalai after Rajini requested him to act.
The scene where Rajini enters into a ladies hostel and gets terrified by a snake was shot at Chakra House, Alwarpet. A snake was brought specially for the scene. Owner of the snake earlier worked in previous films of Rajini. Suresh asked his assistants Nagappan and K. Natraj to check the details about snake charmer. Suresh recalled that he covered his nervousness with his smile. Suresh told Prakash, the film's cinematographer to use zoom lens so that he could adjust a camera according to the situation. After the scene was finished, the members of the crew enjoyed the shot. Suresh congratulated Rajini and asked him how "did he performed so well and was it planned ?", For which Rajini answered it was not planned and expressions in the scene were a result of his fear. In the same scene, Shanmugasundaram came with initial dialogues to convey the fear of Rajini. Suresh felt that dialogues were reduntant in such situation. Rajini insisted to keep Kadavule Kadavule (Oh God! Oh God!) as the dialogue. Suresh agreed to keep the dialogue as it went well into the situation of the scene. Suresh Krissna later revealed to television anchor Gobinath Chandran that nobody on set realised that the snake's mouth was not stitched, and its fangs were not removed. It was only after filming ended for that day that the director came to realise that Rajinikanth's life was at risk the entire time.
Suresh wanted the picturisation of "Vanthenda Paalkaaran" to be vibrant and colourful stating that he got inspired from the Hindi songs of Amitabh Bachchan. The scene where Rajini shows his face to the camera was extended in slowmotion by Suresh as fans will feel as if he looks towards the audience. The song was choreographed by Prabhu Deva. The title song "Annamalai" where Rajini and Kushboo appeared in a periodic costumes was shot at Fern Hill Palace Hotel while the matching shots were shot at Sivaji Gardens. Suresh shot the song sequence in a technique where the lip sync is perfect while the dance movements being fast revealing that he got inspired from the song "Mamavukku Koduma" from Punnagai Mannan (1986).
Suresh Krissna was responsible for the words 'SUPERSTAR' forming in blue dots on the screen followed by the words 'RAJNI' in yellow, which became set standard for all future Rajini films. Annamalai set another benchmark of introducing Rajini's character through introduction songs.
The music of the film has been composed by Deva, with the lyrics penned by Vairamuthu. Annamalai marked Deva's first collaboration with Rajini. KB chosen Deva as a composer due to a misunderstanding with Ilaiyaraja. Rajini and Suresh were initially worried with the choice of Deva. When Suresh met Deva, he had already composed the song "Annamalai Annamalai" when Vasanth was initially the director of the film.
The song "Vanthenda Paalkaaran" is said to be inspired from a Kannada poem about cow which Rajini had suggested, the poem talked about the cow which is a deity and useful to the human. Vairamuthu grasped the core of the poem and added the details of cow being helpful and also added image boosting lyrics in the song to cater his fans.The tune for the song was taken from a marathi fishermen song " Mi Dolkar Daryacha Raja ".
The dialogues from the film was used in the song "Rathiri", composed by Santhosh Narayanan for Pizza (2012).
During the time of shooting, political scenario wasn't quite favourable to Rajini. The new government of Jayalalitha implemented a new rule where posters of films were prohibited in the city. Luckily, the lack of promos only increased the hype and worked greatly to the film's advantage.
Annamalai topped the Chennai box office on its opening weekend grossing ₹28 lakh. The film was a blockbuster and completed a 175-day run at the box office. The film is rumored to have grossed about ₹14 crore at the box office selling 1 crore tickets and was the highest-grossing film in Rajinikanth's career until 1995 when the record was broken by Baasha. The collections of Annamalai sent tremors everywhere. Annamalai exceeded normal regional collections making the film producers all over India sit up and take notice. With Annamalai, Rajini's range increased and made him the highest paid actor in India till now. Tamil Manila Congress and DMK ally prioritized 'Annamalai Cycle', and won the 1996 elections by a huge margin.
Jai stated that his character from Engeyum Eppodhum (2011) "was almost modelled on the lines of Rajini Sir in the first half of Annamalai". Suresh Krishna directed Aarumugam in 2009 which critics compared with Annamalai due to its similar plot and characterisations.
The quote from the film that became popular were: "Naan Solradaiyum Seiven, Soladadeiyum Seiven" (English: I’ll do what I say, I’ll also do what I don’t say). The scene where Rajini challenges Sarath Babu was included by Behindwoods.com in its list of "Top 20 Mass Scenes".
The scenes from the film were parodied in Parthale Paravasam (2001), Boss Engira Bhaskaran (2010), Karuppasamy Kuthagaithaarar (2007) and Thamizh Padam (2010).