The purpose of this paper is to examine the mediated musical culture through the keywords of "emotiveness", "ritualizaion" and "symbolization" as the characteristics of media extracted from the symposium 2 on July 4^<th>, 2010. This paper is based on my fieldwork through observations and interviews with middle-aged and elderly male guests of folksong pubs [foku sakaba] and gig venues in Kyushu, Kansai, Aichi and Tokyo areas since 2007. I focus on elder amateur guitarists because baby boomers [dankai sedai] reached to 60 years old, at the retirement age from regular companies in Japan, in 2007 and they started coming back to their interests of their younger days, which singing folksongs to their own guitar accompaniment [hikigatari]. This paper on the folksong community presents the changing role of music bound to the specific generation in the process of generalization. It is revealed that the folksong community in larger city (Fukuoka City) tends to be pastime. In contrast, in the folksong community in smaller cities (Saga and Imari City), folksong are used as a trigger to vitalize the local communities as music is the bond between the parents' and children's generations. In the previous fieldwork on Japanese high school pupils, I found the tripartite layer of categories in popular music-personal music, common music and standard. Therefore, in this paper, how middle-aged male amateur guitarists pass their generation's music to the next generation as well as how they sympathize with each other through folksongs is investigated. It is found that the crossroad of the woof (contemporaneity) and warp (succession) of Japanese folksong creates a new category of popular music such as 'empathy music' or 'entrustment music'. Through this new category, the parents' generation entrusts their passion of youth to children's generation.