In the late 2010s, Ajith pivoted toward socially responsible cinema, often via official remakes of Hindi hits. Nerkonda Paarvai (2019), a remake of Pink , saw Ajith playing a retired lawyer with bipolar disorder fighting for consent and women’s rights. The film was notable for its restraint: Ajith’s character does not throw a single punch in the climax; instead, he wins via legal argumentation. This marked a departure from the "mass" hero who solves problems with violence.

A defining feature of Ajith’s middle career is the exploration of split identities or dual roles. The seminal film Vaali (1999), directed by S. J. Surya, remains a masterclass in villainous pathos. Ajith played Deva (a mute, virtuous man) and Shiva (his deaf, psychopathic brother). Unlike conventional Tamil films where the hero’s evil twin is a caricature, Ajith’s Shiva was menacing yet pitiable. This performance established his ability to humanize toxicity, a trait he revisited in Villain (2002) and Citizen (2001).

Conversely, the "gentleman" archetype appears in films like Kadhal Mannan (1998) and Dheena (2001). In Dheena , he transformed from a romantic hero into a rugged action star, setting the template for the "angry young man" of the 2000s. This dichotomy—suit-wearing professionalism versus raw, emotional violence—allows Ajith to appeal to both urban elites (through films like Varalaru , 2006) and rural masses.