Klein published "Woody Guthrie: A Life" in 1980 and "Payback: Five Marines After Vietnam" in 1984. He was a political columnist for "New York" from 1987 to 1992, winning the Peter Kihss Award for his reporting on the 1989 race for mayor of New York. In May 1992 he joined "Newsweek" and wrote the column "Public Lives," which won a National Headliner Award in 1994. "Newsweek" also won a National Magazine Award for their coverage of Bill Clinton's 1992 victory. From 1992 to 1996 he was also a consultant for CBS News, providing commentary.