[6] 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.

[7][full citation needed] In 2009, he became a regular cast member in Radio Star, the main segment of MBC's Golden Fishery,[6] 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.[8][9] 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.

In 2017, Red Velvet released a remake of his 1996 song "Rebirth" (환생) through SM Station.

[17][18] In July 2020, Yoon rushed back to Korea to tend to his ill mother, and she died in September of that year.