He learned from local musicians Clive Zanda, Len 'Boogsie' Sharpe, Raf Robertson, Earl Rodney, and Toby Tobias.

He began recording albums with Lord Kitchener, Superblue/Blue Boy, Valentino, and Crazy.

Blending Calypso music and jazz with bossa nova allowed Villafana to form his own style.

He entertained crowds in Trinidad and St. Croix with solo performances and appearances on radio and television.

[3] Villafana moved to the United States, intending to enroll in the Berklee College of Music.