Masak was born in Chicago to Floyd Louis Masak and Mildred Alice (Rudy) Masak. His mother was of Irish descent and his father of
Czech Bohemian descent. His paternal great-grandfather, Karel Masák (1861-1899), was an immigrant from Zvěrkovice near Týn nad Vltavou.
He began working as a stage performer, and mostly was involved in theater until transitioning to film and television becoming a familiar character actor.
The Army provided Masak with a platform to display his all-around talents for performing, writing, and directing. In 1960-61, he toured the world doing vocal impressions in the all-Army show entitled "Rolling Along".[citation needed]

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