In 1990, he made his debut as a guest singer for
015B. In 1991, he announced his first album
Like the first time we met () as a solo singer which drew huge public interest. He has continuously collaborated with 015B since. 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. In 2009, he became a regular cast member in
Radio Star, the main segment of
MBC's
Golden Fishery, 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, an incurable inflammatory bowel disease. He became the co-host of SBS's
GO Show in April 2012. In February 2013, he became the co-host of SBS's
Hwasin - Controller of the Heart. 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" () through
SM Station. In 2019, he was a judge in the
JTBC talent show
Superband. In 2021, he will become the main host of
Mysterious Record Shop. The other co-host will be
Wendy,
Kyuhyun, and
Jang Yoon Jung. A live recording of Yoon's song "Uphill Road" was released as a digital single on August 1, 2025. ==Personal life==