 His work in "Thulladha Manamum Thullum" (1999), where he portrayed a comedic role of a man slowly becoming a transgender, won him further critical acclaim.Throughout his career, Vaiyapuri has often appeared in films starring Kamal Haasan and the actor selected Vaiyapuri for a major supporting role in the actor's "Mumbai Xpress" (2005).Vaiyapuri was later cast as a transgender in Mani Ratnam's "Raavanan" (2010), which he described as a "major turning point" in his career.