Originally from Syria, Youssef Kassab began learning the oud and studying voice with his uncle at an early age. He continued his studies at the Damascus Conservatory, specializing in qanun (zither) and classical Arabic music vocal repertoire. There he recorded and performed with the Syrian Radio Orchestra as a vocalist.

In 1970 he moved to New York where he has been performing in concerts and festivals throughout the United States and Central America. In 1982 he joined the Near Eastern Music Ensemble as a principal vocalist. Youssef Kassab is one of the master performers of classical forms such as the Arabic Muwashshahat (classical Arabic/Andalusian vocal music), Al-Qudud Al-Halabiyya (traditional vocal repertoire from Aleppo, Syria), and 19th and early 20th century Egyptian vocal music.