Yoon Shi-yoon played a semi-rebellious teenager in his debut acting project in the MBC daily sitcom High Kick Through the Roof. His work in the sitcom earned him Best New Actor nominations at the 46th Baeksang Arts Awards and the 2009 MBC Entertainment Awards. He next starred in the hit KBS2 series Baker King Kim Tak-gu, which logged a viewership rating of 50.9 percent for its final episode. His performance in the drama won him numerous acting awards, including an Excellence Award at the 2010 KBS Drama Awards. In 2016, he joined the third season of the KBS2 variety show 1 Night 2 Days, in which he received the Rookie Award and the Top Entertainer Award at the 2016 and 2018 KBS Entertainment Awards, respectively. In 2018, he led TV Chosun’s Grand Prince, which scored him a nomination for an Excellence Award at the 6th APAN Star Awards. That same year, he played dual roles in the SBS legal drama Your Honor, which gave him an Excellence Award at the SBS Drama Awards.

Yoon Shi-yoon began his mandatory military service on April 28, 2014. He was discharged on January 27, 2016. He loves to read and shared in an episode of SBS’ One Night of TV Entertainment that his love for books came from his mother.