At a very young age, Xylouris discovered his musical inclination (all three male siblings learned the basics of how to play the mandolin and other instruments alongside their friends at village feasts and peer gatherings) and besought his father Giorgis to purchase him a Cretan Lyra, (the three-stringed or four-stringed Cretan fiddle analogue, which is played held upright, usually supported on the knee), a significant investment at the time. Giorgis resented the notion of his elder son becoming a musician, which was deemed somewhat menial and rather disreputable as a full-time occupation, and preferred that he attain higher education instead, which would enable him to improve the overall outlook of his life, and escape the circumstances of poverty and hardship that plagued his fellow villagers. Thus, Giorgis fiercely opposed his son's demand at first. However, between the boy's entreaties and the exhortations of local school teacher Menelaos Dramountanis who had identified Xylouris' enormous potential and considered his singing voice a decisive asset, Giorgis acquiesced and Xylouris acquired his first instrument at the age of twelve. After an apprenticeship under the tutelage of the experienced lyra player Leonidas Klados, Xylouris started performing at social functions and local festivities throughout the region and later across the island, usually accompanied by his younger brother Giannis who played the lute. In those events, gifted musicians were being generously rewarded, and not just by one single organizing party, but by all participants to the celebration who, if affluent enough, as per custom, would present the orchestra with banknotes for every single song or dancing tune they requested be played. A musician's reputation grew by crowd acclaim and word of mouth, once they were proven able to please, stir and entertain their audience for the duration of the event, which could sometimes last for days on end. Having earned such a reputation of a capable musician, at age seventeen Xylouris again surprised his parents when he decided to move from Anogeia to the city of Heraklion, making nightly appearances at the venue "Kastron" (Greek: Κάστρον, literally meaning Castle, which invokes the city's Medieval name) and aspiring to become an established professional musician with full financial independence. At first, little was gained in terms of headway, and making ends meet in the city was challenging. The audience, mostly urban and somewhat upper class, had moved away from Cretan traditional music, Xylouris' own turf, and had become much more accustomed to European rhythms and tunes, looking down upon the "old men's music" of their rural contemporaries and counterparts. In such an environment, folk musicians struggled to adapt and survive financially, not least due to their utter lack of multilingual term familiarity, which foreign lyrics seemed to necessitate. Furthermore, city musicians were distrustful of all newcomers and unwilling to yield them any professional breathing space. By his own account, Xylouris was reluctant to admit to his father that he was facing great hardships at that time, and instead assured him to the contrary. Gradually, he managed to develop a personal following, found a firm foothold, and carved out a niche for himself. His friends and admirers not only provided encouragement, but organized gatherings for him to play music at, earn a living from, and attract additional support by. In 1967 he took an unprecedented step and established in Heraklion the first exclusively Cretan music hall, which he named "Erotokritos", in honor of the great poetic work of the same name. In the course of time, Xylouris not only managed to find acceptance as a musician in Heraklion, but he was also able to turn his demanding urban audience around, causing them to rediscover, appreciate and preserve Cretan traditional music for future generations. And a few years later, he would manage to captivate the attention of the Greek national audience in its entirety.