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Siegel's first professional broadcasting job was at WGLI in Babylon, New York, where he "did morning newscasts and a show that was part phone-ins, part Top Forty, all under the pseudonym Bob Charles." After a year at Columbia University Graduate School of Journalism, Siegel left academia for good and worked for WRVR in New York from 1971 to 1976.
Siegel was hired as a newscaster for NPR in Washington, D.C., in 1976, and he has held various news and production jobs at NPR since then. Since 1987, he has been a host of All Things Considered. He took a short break in 1992 to host Talk of the Nation, NPR's call-in talk show.
Siegel grew up in Stuyvesant Town—Peter Cooper Village, in New York City. He is the son of Joseph, a commercial education teacher, and Edith, a secretary at Stuyvesant High School. His maternal grandfather claimed to descend from rabbinical scholar Mordechai Yoffe  and Siegel has identified on-air as Jewish. After graduating in 1964 from Stuyvesant, Siegel studied at Columbia University, graduating in 1968. During this time he was an anchor for the reporting of the 1968 Columbia demonstrations at the college radio station, WKCR-FM.
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