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In 1978, he wrote Boxing For Beginners, an instructional and historical book on boxing. He also wrote for Boxing Illustrated and The Ring during this period.
In 1980, Bernstein joined ESPN as boxing analyst for the Top Rank Boxing series. He stayed at ESPN until 2003, and during that time he also worked as a reporter for SportsCenter, covering major boxing matches, Major League Baseball, the NBA and the NFL Draft. He also wrote and hosted the series Big Fights Boxing Hour for ESPN Classic. In 1988, he won the Sam Taub Award for excellence in boxing broadcasting journalism and in 2012 he was inducted into the International Boxing Hall of Fame.
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In 1988, Bernstein recorded his first album My Very Own Songs, with original songs about television and sports. He released Let The Games Begin in 1996. In 1998, he also began a career as a live musical performer. Since then he has performed at major casinos such as Caesars Palace, the Mandalay Bay and The Riviera, as well as many Indian and Riverboat casinos around the United States.