Born in Cabra, Dublin,[6] Masterson grew up in a musical family, and learned to play the pipes and other instruments at an early age.
He was encouraged by his parents Frances and Jim, who both played traditional music, and by his uncle Jimmy O'Reilly, a squeezebox player from Multyfarnham, County Westmeath.
[7] Masterson first played with the Pipers Club Céilí Band, and his first group was Tipsy Sailor, which included Gerry O'Connor (banjo) and Fiách Ó Broin (flute).
They initially intended to form a trio with guitarist Declan Sinnott,[9] but then expanded the group to include Irish musicians Keith Donald (alto sax), Eoghan O'Neill (bass), Brian Calnan (drums), and Davy Spillane (uilleann pipes).
[12]: 11 They performed in Budapest on 12 July 1985, followed by a further two gigs in Hungary and an appearance at the Dranouter festival in Belgium in early August, prior to their English tour.