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Jason Louis Kladiva was born in Melrose Park, Illinois, the son of a military father Robert Kladiva and stay-at-home mother Susan Kladiva. He is of Bohemian descent. He performed in numerous theatrical school plays growing up and worked at a movie theater in high school selling popcorn and running the projector but was told he would never be on the screen. The film Prairie Rose (2005, which he starred as Agent Winslow, premiered at that very theater. His career started in 1983 when he announced a cartoon on The Bozo Show on WGN-TV (Chicago). From there he appeared in a commercial for his cousin who was in advertising. In the early 1990s, Jason gained work as an extra and doing stunts on numerous television miniseries. Jason took to radio as the host of Vintage Base Ball This Week, The Morning Show and The Eclectic Blender on WVLP 98.3 FM (Valparaiso, Indiana) and would later host the short lived The Jason Kladiva Show on the same station.