After the success of his maiden venture Minsara Kanavu (1997), Rajiv Menon was signed by producer Kalaipuli S. Thanu to direct a film under his production in the final quarter of 1998.
Rajiv first announced he had begun pre-production work on a project titled Theekkul Viralai Vaithal during November 1998, with the title taken from a line by Subramania Bharati.Rajiv subsequently wanted a bigger storyline and scripted a screenplay based on the Jane Austen novel, Sense and Sensibility, and the project was renamed as Kandukondain Kandukondain.The title was inspired from the phrase 'kanden kanden Seethaiyai kanden' from Kambar's epic Kamba RamayanamRajiv claimed that the story of two sisters reflected in the film were reminiscent of him and his brother through difficult parts of their livesThe film was initially launched as a multilingual project in Tamil, Telugu, Hindi and Malayalam, though it only released in Tamil with a subsequent dubbed Telugu version titled Priyuraalu PilichindiRajiv first penned the story in English and then dictated the dialogue in Malayalam which were then translated by Sujatha into Tamil.After most of the production was complete in Nov 1999, Menon wanted a rough copy of the film to be previewed by the village audience first, to ensure that they could relate to the subject.After showing parts of the film to audiences in Udumalpettai and Pollachi, the team eventually held a group discussion before thanking the volunteers with gifts.Tabu was the first to be cast in the film and signed on to play the role of the elder sister Sowmya, while casting the younger sister's character of Meenakshi took longer to finalise.Rajiv first approached Malayalam actress Manju Warrier, who liked the script but was hesitant to commit to appear in the filmHe next discussed the role with Soundarya, who was keen to see the entire script before signing the project.As Rajiv Menon was still finalising the climax then, he opted to explore other optionsAishwarya Rai was then signed on to the project, making her third appearance in Tamil films after roles in Mani Ratnam's Iruvar (1997) and Shankar's Jeans (1998).Despite being barraged with Hindi film offers, Aishwarya claimed that she was a large fan of Menon's work and could strongly identify with the character, and hence accepted the offer.Writer Sujatha and Menon presented two different points of view in the female leads and while Sowmya accepts destiny, Meenakshi wants to seek out her own choices.While finalising the character arc of Sowmya, Menon drew inspiration from a person with who he was familiar with.Initially, Rajiv had cast Prabhu Deva, the lead actor of his previous film, Minsaara Kanavu in a leading role, but Prabhu opted out for unknown reasons.For the role of a former army general, Menon initially attempted to cast Parthiban but the actor's strained relationship with producer Thanu meant that they could not collaborate.Arjun was also approached but he was set on doing a different genre of films during the period.Eventually, Rajiv finalised Malayalam actor Mammootty to play the role of the major.Rajiv Menon approached Prashanth for the role of the struggling filmmaker, however, the actor demanded that he be paired opposite Rai and not Tabu.In January 1999, Rajiv Menon met and narrated the script to Ajith, who had been recovering from a back surgery. The actor later agreed to be a part of the film.While writing the character, Menon was inspired by his own experiences as a junior technician looking to make a breakthrough in the film industry.Between signing the film and the eventual release in May 2000, Ajith had significantly expanded his box office appeal through the commercial success of his other films.Abbas was also cast in a further lead role of a young businessman, while Chiyaan Vikram dubbed for his character.Malayalam actor, Unnikrishnan Namboothiri, made his debut in Tamil cinema as the bed-ridden grandfather.Hindi actors Dino Morea and Pooja Batra played cameo roles in the film.Cameraman Arvind Krishna appeared in a small role as Ajith's friend.Rajiv Menon and Dhanu retained several of the technical team from his previous venture, with only Sujatha added to write the dialogues.Furthermore, a cinematographer himself, Menon opted not to be so in the project and appointed Ravi K Chandran to control the camera.Though Rajiv later revealed that directing and being cinematographer at the same time was 'strenuous,' he had almost shot 30 percent of the film as Ravi had been briefly unavailable.The costumes were designed by Nalini SriramScenes with Mammootty's army soldier character were shot in Munnar from February to April 1999, close to the outbreak of the Kargil War.The team were able to borrow a former military helicopter for the sequences.A large portion of the film's first half was shot in the Kanadugathan area of Karaikudi.The team convinced industrialist M. A. M. Ramaswamy to lend them his palatial Chettiar mansion for filming, and were able to secure permission as the producer Thanu was an acquaintance.Rajiv submitted a one-page synopsis of the film to Ramaswamy for permission, and the industrialist agreed under the condition that a death scene was filmed elsewhere.Thus, Rajiv Menon eventually hired the Rao Bahadur house for the extra scenes.During the shoot in the Chettiar mansion, Menon cited that the unit bonded with Rai and Tabu becoming good friends.Most of the first half of the film was shot within a week.In May 1999, the crew along with Rai and Abbas went to Scotland to film the title song on a lake in Dornie with the backdrop of a castle, the Eilean Donan.Rajiv wanted the location particularly to show that Rai's character of Meenakshi was living in a fantasy world and shot the song with a blue and green theme.In comparison, the team wanted to contrast the colours for Tabu's song by picking red and brown as the main colours.The song Enna Solla Pogiraai was shot in Egypt over a period of one week.The song 'Kannamoochi Yenada' was shot with the lead cast at the Kushaldas Gardens in Chennai.The film was delayed for six months due to the success of Rai's Taal and Hum Dil De Chuke Sanam, which prompted the revival of other projects she had signed up to at the period.Furthermore, Rajiv's insistence that Rahman reworked some of the music to provide a better fusion of classical and contemporary music, also postponed progress.The film subsequently ended production, six months behind the schedule charted out by Rajiv Menon.The audio release function of the film was held, with Kamal Haasan in attendance.During post-production, the film ran into problems with dubbing with Mammootty initially showing hesitance for dubbing for his character, before eventually giving in to the producer's demandsThe film was made at a budget of 4 crores.