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Stein grew up in New Rochelle, NY and graduated from New Rochelle High School in 1966. He is married with two children, Sadie and Charlie. He currently splits his time between residences in New York and Arizona
Stein wrote for Ramparts and New Times magazines in the 1970s, and originated Esquire's "Ethics" column in the 1980s. During the 1990s he wrote a column on television ethics for TV Guide. As part of the New York media scene of the early 1980s he was a member of the inaugural Rotisserie League formed by Daniel Okrent.
He is the author of novels and memoirs, including satirical political commentary related to his transition from liberal to conservative viewpoints. His first book, Tiny Tim, a biography of the entertainer, was published in 1976.
- Stein, Harry (1976). Tiny Tim. Playboy. ISBN 087223455X.
- Stein, Harry (1983). Ethics (and Other Liabilities). St. Martin's Griffin. ISBN 0312265573.
- Stein, Harry (1988). One of the Guys. Simon&Schuster. ISBN 0671557041.
- Stein, Harry (1996). The Magic Bullet. Delta. ISBN 0440613892.
- Malkin, Peter Z.; Stein, Harry (1990). Eichmann in My Hands. Warner Books. ISBN 0446514187.
- Stein, Harry (1997). Hoopla. Dell. ISBN 0440221307.
- Stein, Harry (1997). Infinity's Child. Dell. ISBN 0440223601.
- Stein, Harry (2000). How I Accidentally Joined the Vast Right-wing Conspiracy. Delacorte Press. ISBN 038533396X.
- Stein, Harry (2004). The Girl Watchers Club. HarperCollins. ISBN 0066211727.
- Stein, Harry (2009). I Can't Believe I'm Sitting Next to a Republican. Encounter Books. ISBN 159403253X.
- Stein, Harry (2012). No Matter What...They'll Call This Book Racist. Encounter Books. ISBN 1594036004.
- Stein, Harry (2013). Why We Won't Talk Honestly About Race. Encounter Books. ISBN 159403706X.
- " "Manhattan Institute Scholar: Harry Stein". Manhattan Institute for Policy Research. Retrieved August 4, 2009.
- I Can't Believe I'm Sitting Next to a Republican - interviewed by Jamie Glazov, editor of Front Page magazine - August 10, 2009
- Booknotes interview with Stein on How I Accidentally Joined the Vast Right-Wing Conspiracy, August 20, 2000.