He came in contact with the music club ‘Sochangsa’ and his association with the club helped him develop his passion for music. His debut in the world of music happened in 1990 when he worked with the producer group ‘015B (ko)’. He worked as a guest vocalist, lending his voice for the track ‘In an Empty Street’.
He released his first studio album ‘Like the first time we met’ on May 12, 1991 under the label ‘Hyundai Sound’. The album garnered attention, giving him recognition as a solo singer. While coming up with other studio albums that showcased his own style, Yoon continued to actively collaborate with ‘015B’.
Among his studio albums, the first three that encompassed mostly ballads were his collaborative efforts with other composers. Starting from his fourth album, he came up with ballad songs of his own style that can neither be placed under the bracket of banal nor under generic.
Discography of Yoon includes other studio albums, such as ‘Sorrow’ released on November 15, 1992 and ‘The Natural’ released on August 12, 1993.Many other albums came out under the label ‘Daeyoung AV’.
He is also a talented and popular songwriter in Korea. Apart from penning down his own songs, Yoon has also contributed by writing songs for other artists as well. These include songs like ‘On the Street’ for Sung Si-kyung and ‘You Mean Everything to Me’ for Lena Park.
After making a mark in the world of music, he forayed into acting, while continuing with his musical pursuits. His debut on the big screen happened in 2000 with a cameo role in the film ‘Can hardly stop them’. He then featured in the South Korean TV series ‘The Unstoppables’ that aired on SBS from December 18, 2000 to February 22, 2002.
In 2001, he founded the South Korean record label and talent agency ‘Mystic Entertainment’ (Mystic89), along with Lee Hak-hee. He is presently the CEO and Chairman of the company.
Over the years, ‘Mystic89’ has emerged as a professional and organized record company under the leadership of Yoon. The record label is not only active in the music industry but is also a key player on other platforms, such as movies, entertainment programs and dramas.
The romantic comedy flick ‘Spring Bears Love’ that released on July 16, 2003 featured him in the role of Ji-seok. He then essayed the role of a professor in the situational comedy ‘Nonstop 4’which was directed by Seo Chang-man, Kwon Ik-jun and Lee Ji-sun. The sitcom was aired on MBC from September 15, 2003 to October 1, 2004.
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Next he played the role of a plastic surgeon in the October 27, 2005 released romantic comedy film, ‘The Beast and the Beauty’.
In the romantic comedy melodrama time-travel film ‘Project Makeover’, he was featured in the role of Mr. Yoon. That year, he became one of the three MCs of the program ‘Radio Star’. The program presently forms the main segment of the South Korean talk show, ‘Golden Fishery’.
The first episode of ‘Radio Star’ was broadcast on May 30, 2007 with Yoon, Shin Jung-hwan and Kim Gura. In 2009, Yoon became a regular cast member of the show which presently features him along with Kim Gook-jin and Kim Gu-ra as hosts.
Meanwhile in 2008, he remained a member of the South Korean comedy variety show ‘Family Outing’ that aired on SBS. The years that followed saw him as the host of many other television shows namely ‘GO Show’ (2012), ‘Hwasin - Controller of the Heart’ (2013), ‘Barefooted Friends’ (2013) and ‘Secretly Greatly’ (2016-17).
He also remained as a part of the South Korean comedy television series ‘Hilarious Housewives’ which was aired on MBC from March 2, 2009 to September 4, 2009.Around this time, he also served as the judge of ‘Superstar K’, a South Korean talent show series.
He also appeared in several TV series, playing cameo roles. These series include ‘High Kick! 2’ (2009-2010), ‘Smile Again’ (2010-2011) and ‘Persevere, Goo Hae-Ra’ (2015).
His album ‘His Walk of Life 2010 Yoon Jong-shin’ was released on October 28, 2010 under ‘Mystic89’ and ‘Windowmill Media’. The following year, he came up with another studio album titled ‘His Walk of Life 2011 Yoon Jong-shin’ which was released on December 6, 2011 under ‘Mystic89’ and ‘Mirrorball Music’.
He also guest-starred in several television variety shows namely ‘Running Man’ (2014, 2017), ‘You Hee-yeol's Sketchbook’ (2015) and ‘Knowing Bros’ (2017).
He appeared as himself in the third episode of the South Korean television series ‘The Producers’ that aired on KBS2 from May 15, 2015 to June 20, 2015.