In 2004, Yoon made his debut as rapper Mingyu in the musical Sonagi, also known as Rain Shower, while attending Kyungmin University. Despite having a small role, his performance left a lasting impact. The musical, based on the novel by Hwang Soon-won and directed by Yoo Hee-seong, revolves around a vague memory of first love. Yoon also secured minor roles in the MBC musical
I Forgot His Name. In 2005, he was cast in the musical
Love Quilt. Yoon's breakthrough came in 2012 when he landed his first leading role in the musical
Proposal after a competitive audition process. With fellow actor Jung Uk-jin, Yoon won the role of Min-ho, a non-regular sports center instructor, beating out 200 other contestants for the part. He also secured the lead role of Kim Jong-wook in the sixth season of
Finding Mr. Destiny the same year. After six years, Yoon returned to the theater for his second play,
Puzzle (2013), which is a Korean adaptation of the play
Point of Death by British writer
Michael Cooney. Yoon played the supporting role of Travis in alternating performances with two fellow actors, Won Jong-hwan and Park Ki-duk. The play was performed from September 7 to November 17, 2013, at the Daehak-ro Happy Theater. In 2021, Yoon landed a supporting role in the
tvN drama
Hometown Cha-Cha-Cha through an audition, playing the character Choi Geum-cheol, the owner of a tool shop in Gongjin, who is also Du-sik's best friend and Bo-ra's father. Following the success of the drama, Yoon signed an exclusive contract with D-Plan Entertainment, marking the beginning of his active career in television. == Personal life ==