Poposki, was born in Ohrid, at that time still part of Yugoslavia but now in Macedonia, to Dominika and Nikola Proeski from Kruševo, his hometown, where he spent most of his childhood. After his musical talent was discovered at the age of 12, he was chosen to perform at the popular children's song festival Zlatno Slavejče in Skopje. This was his first public music performance; however, his successful career began in 1996 when he participated in the teenage music festival Melfest in Prilep.