Vaali (1999) - Deva, Shiva
This was the first time Ajith did a double role in his career, and it was considered by many as a hasty decisionHowever, Ajith exceeded expectations and won his first Filmfare Award for his portrayal of the brothers, Deva and ShivaCitizen (2001) - Arivanandham and SubramaniSaravana Subbaiah was supposed to direct one more film with Ajith, titled Itihasam. However, this film, written by Sujatha, was shelved due to production issues.There was a Kaadhal Mannan connect in this film as Pandiyan's role was first supposed to played by Gemini GanesanVillain (2002) - Shiva, VishnuThis was the first collaboration between Ajith and KS Ravikumar. The story was written by Yugi SethuIt does seem that a double role and a Filmfare go hand-in-hand for Ajith as he picked up his second award for VillainAttagasam (2004) - Guru, JeevaCrossing multiple financial hurdles, the film released to much fanfare on Deepavali. And... the Thala anthem was here to staySaran, in an interview, revealed that Ajith accommodated his dates for this film to help the director helm the Kamal haasan-starrer Vasool RajaVaralaaru (2006) - Jeeva, Shivshankar, VishnuAfter multiple financial issues, title and smoking controversies, the film released on Diwali 2006 and became one of the biggest hits in his career. Ajith won his third FilmfareThe film was initially written for Kamal Haasan. Many heroes were skeptical to take up the film due to the characterisation of the protagonist.Billa (2007) - David Billa and SaravanaveluVishnuvardhan wanted to direct an original film with Ajith but later zeroed in on the Billa remake. This was just the second time a Tamil film was remade in Tamil itselfThis was the first collaboration between Ajith and Nayanthara who would go on to star in multiple blockbuster films. Ajith was nominated for a FilmfareAasal (2010) - Shiva and JeevanandhamAjith was credited as an assistant director in this film. Saran revealed that Ajith wanted to do away with the usual masala cliches and deliver an international filmWhile Harris Jayaraj and Yuvan Shankar Raja were speculated to be part of the project, it ultimately became the 50th film for Saran and Ajith's frequent collaborator, Bharadwaj