The following year, after portraying one of the homeless in Jang Sun-woo's documentary-style Bad Movie, he gained cult notoriety for his performance in Song Neung-han's No. 3 as a gangster training a group of young recruits, winning his first acting award at the Blue Dragon Film Awards. Following this, Song was cast in several supporting roles before his high-profile appearance as Han Suk-kyu's secret agent partner in Kang Je-gyu's blockbuster thriller Shiri. In early 2000, Song's popularity increased with his first leading role in the box office smash The Foul King, for which he did most of his own stunts.