In 1990 he made his debut as a guest singer for 015B (ko).
In 1991, he announced his first album Like the first time we met (처음 만날 때처럼) as a solo singer which drew huge public interest . After that he collaborated with 015B continuously.
Yoon completed high school at Daewon Foreign Language High School and studied Korean Language and Literature at Yonsei University, graduating in 1993. He joined a music club called Sochangsa (소창사) where he nurtured his love for music.
In 2000, he made his movie debut in Can hardly stop them with a cameo along with the Director, Kim. He became active in the field of entertainment and, in 2003, took a role in a sitcom Nonstop 4 where he played a professor.
He owns a talent agency/record label called Mystic89, founded in 2001 with Lee Hak-hee.
Yoon married former professional tennis player Jeon Mi-ra in 2006 and have three children together.
In 2009, he became a regular cast member in Radio Star, the main segment of MBC's Golden Fishery, and in SBS's Family Outing. He has also been a judge for seasons 1-3 and 5-7 of Mnet's talent show Superstar K.
In February 2012, he made an appearance on SBS's Healing Camp, Aren't You Happy where he announced that he had Crohn's disease which is an incurable inflammatory bowel disease. He became the co-host of SBS's GO Show in April 2012.
From April 2013, he is the regular host of SBS reality show, Barefooted Friends.
In 2017, Red Velvet released a remake of his 1996 song "Rebirth" (환생) through SM Station.
