The tale of Gangta (H.O.T.) and BoA, when the SM buyout circus was happening, touched some minds.
Gangta was with SM for 30 years . He joined SM as a trainee on 1994 even before SM Entertainment was incorporated on 1995, and has never left it, although his status after SM was bought out by Kakao is unclear now.
30 years under a company is rare in the modern world, especially in the entertainment world.
BoA joined SM on 1998 as a trainee and has stayed with it for 26 years.
Lee Sooman gave both Gangta and BoA director positions although what will happen to that position under Kakao is unclear.
Among the idols who are prominent, Jihyo (Twice) seems to be the idol who stayed in the same company for the longest. There is GDragon, but because he began as an SM trainee, he is disqualified no matter how long he was in YG since he was with another company even for a short time.
It is rare in the West, but the Japanese baseball team Yomiuri Giants never lets someone who spent a second out of its team, even as a coaching staff or major leagues , to be its Manager or other important staff positions. (There was one exception but he only served as a coach in another team for 2 years after 18 years in the giants as a player) Some teams still care about loyalty.
Because Jihyo started in JYPE on 2005 as a trainee and stayed there for 19 years, longer than some 2PM members even, she carries a very heavy weight in JYPE, probably next to JYP himself. It is likely that after Twice stops its activities Jihyo will become a director or something and continue to work in JYPE for a long time. Yubin of Wonder Girls was the singer who lasted the longest in JYPE, but since she started with another company, she was not Senior to Jihyo.
On contrast to these loyal singers, some acts changed their company quite often.
APink had four masters.
On 2011 it began under ACube Entertainment, 2016 PlanA Entertainment, 2019 PlayM Entertainment and on 2021 IST Entertainment.
So APink went through 4 owners in 13 years.
4 Masters.
Of course any discussion with whyknock usually features IU.
IU is a legend in a strange way - she has had 7, SEVEN, companies during her 17 year career, probably more than the number of her known boyfriends.
IU began with the company which developed Osonyeo (Five Girls), including Uee and the aforementioned Yubin, whose association of that company prevented her from becoming a senior figure in JYPE.
After the company folded, she joined Loen Entertainment on 2008, spending little tile training and debuting on Sep of that year.
However, she moved to Loen Tree on 2012,
Fave Entertainment on 2016,
and Kakao Entertainment on 2017.
So she had 5 masters on her 11th year.
On 2020, she moved to Edam Entertainment, her 6th company, owned by herself.
And then on 2022 Edam Entertainment was sold back to Kakao, so even though the two companies have the same name, its ownership changed and she was owned by Kakao again.
So it is arguable whether IU had 6 masters or 7, but arguably she has the record of having changed companies most often among better-known acts.