Raised in Milwaukee, Wisconsin, Feldman graduated from the University of Wisconsin–Madison with a degree in English in 1970. He worked as a teacher at Malcolm Shabazz Alternative High School in Madison, Wisconsin, before finding work at radio station WORT. Soon after, he worked as a cab driver before coming back to broadcasting, first at Wisconsin Public Radio, then at WGN. He was fired from WGN in 1984, which sent him back to Public Radio. He started his show, Michael Feldman's Whad'Ya Know?, in 1985.
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