He has acted in various television dramas, notably Autumn in My Heart (2000), East of Eden (2008), My Princess (2011), Black (2017), Player (2018), The Great Show (2019), and Dinner Mate (2020).

[7][5] In 2002, Song starred in the action comedy Make It Big by director Cho Ui-seok,[8][9] and also in the Hong Kong film So Close with actresses Karen Mok, Shu Qi and Zhao Wei.

[11][6] The series is the third "season-themed" Yoon Seok-ho TV drama after Autumn in My Heart and Winter Sonata, but did not become as popular as the ones that preceded it.

[5] Meanwhile, in late 2004, just as he was getting ready to start shooting another high-profile TV drama Sad Love Story, it was revealed that the actor had illegally avoided his compulsory military service by submitting tainted urine samples that suggested he was suffering from certain illnesses and was thus unfit for the army.

[14][15] Amidst the press coverage and scandal this aroused, Song agreed to immediately serve his two-year term in the military.

"[31][32] His 30-minute short film Lucid Dreaming, helmed by director Chang of 2008 feature Death Bell, was shot particularly for his fans in China and Japan and released on DVD in early 2012.

[33][34][35] Based on the original comic by Motoka Murakami and previously dramatized in Japan, in 2012's Dr. Jin Song played the titular smart and cold-hearted surgeon who takes a journey back through time to the late 19th century Joseon Dynasty (1392-1910).

[41] Set in 1969 at the end of the Vietnam War, he played a high-ranking officer suffering from post-traumatic stress disorder who falls into an obsessive love affair with his subordinate's wife.

In 2009 he founded his own management agency, Storm S Company (later renamed Better ENT, now majority-owned by KOSDAQ-listed Signal Entertainment Group).