He was born on April 7, 1922, in Trikala where he learned to play the Bouzouki. He moved to Athens in 1946 and recorded his first song the following year "Νύχτωσε χωρίς φεγγάρι" - "Moonless night". Kaldaras wrote the music for song writers such as Kostas Virvos, Eftychia Papayiannopoulou and Pythagoras. His songs were sung by a variety of singers including: Vangelis Perpiniadis, Stelios Kazantzidis, Giorgos Dalaras, Viki Moscholiou, Panos Gavalas, Manolis Angelopoulos, Michalis Menidiatis, Poly Panou, Yiota Lydia and Stamatis Kokotas.