Song joined Kee Kuk-seo's theatre company, which emphasized instinctive acting and improvisation. He made his stage premiere in 1991 in a play called Dongseung and spent the next decade as a stage actor. Although he was regularly approached to act in films, he always turned down the opportunity until taking a role as an extra in Hong Sang-soo's 1996 film The Day a Pig Fell into the Wellat age 30.
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.[citation needed]
It was his award-winning 2000 performance in Joint Security Area as a North Korean sergeant that established him as one of South Korea's leading actors. Song also starred in Park Chan-wook's acclaimed followup, Sympathy for Mr. Vengeance, which centers on a father's pursuit of his daughter's kidnappers. In 2002, Song starred in another major production by Myung Films, YMCA Baseball Team, about Korea's first baseball team which formed in the early 20th century.
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