Since the beginning of the first generation of Kpop, music show wins have always been an important achievements for the artists and their fans. The first win of an artist is always a big moment in their career and is celebrated by all fans. Only the greatest and biggest group in the history of Kpop have managed to gather a high number of wins. And only the most resilient and greatest artist were able to convert their talent in multiple wins across decades.
These are the only artists that were able to win in 3 decades :
Turbo (Joong-kook group) in the late 1990s, early 2000s and with their impressive return in 2015 featuring Yoo Jae Suk.
Im Chang Jung, in the late 1990s, 2000s and with his comeback in 2015 with Love Again :
Shinhwa, in the late 1990s, 2000s and with multiple comeback in the 2010s (early mostly) :
Big Bang, with their recent comeback
Shinee, of course with Don't call me
Rain with his collab with JYP in 2021
Indirect 3 decades run of an artist across multiple groups/solos :
BoA, solo in the 2000s and 2010s, and with GOT the beat in 2020s
Taeyeon/Hyoyeon, with SNSD in 2000s and 2010s, solo in the 2010s and 2020s (Taeyeon) and with Got the beat in the 2020s.
Yunho, with TVXQ in the 2000s and 2010s, and then solo in the 2020s
It's probable that JYP might do it but didn't find datas for him
ONLY ARTIST TO WIN IN 4 DECADES : QUEEN LEE HYORI
She won with Fin.KL in the 1990s and 2000s, solo in the 2000s and 2010s and made a legendary comeback in the 2020s with SSAK3 with Rain to win in the 2020s. Legend.
Shout out to Lulu_Key making the original post ! And idontsleep for asking in that thread !