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Spy was a satirical monthly magazine that ran from 1986 to 1998. Founded by Kurt Andersen and E. Graydon Carter, who served as its first editors, and Thomas L. Phillips, Jr., its first publisher. After one folding and a rebirth, it ceased publication in 1998. It specialized in intelligent, thoroughly researched, irreverent pieces targeting the American media, entertainment industries and making fun of high society. Many issues often featured brief photographs of nudity relevant to a story. Some of its features attempted to present the darker side of celebrities such as Arnold Schwarzenegger, John F. Kennedy, Jr., Steven Seagal, Martha Stewart, and especially, the real-estate tycoon Donald Trump and his then-wife Ivana Trump. Pejorative epithets of celebrities, e.g., "Abe 'I'm Writing As Bad As I Can' Rosenthal" and "former fat girl Diane Brill" became a Spy trademark.
In October 2006, Miramax Books published Spy: The Funny Years (ISBN 1-4013-5239-1), a greatest-hits anthology and history of the magazine created and compiled by Carter, Andersen, and one of their original editors, George Kalogerakis.
For a humorous magazine, Spy often was aggressive about straight feature reporting. In the summer of 1992, it ran the only serious investigative story on President George H.W. Bush's extramarital affairs with Jennifer Fitzgerald and other women. The following year, Spy ran an article entitled "Clinton's First 100 Lies", detailing what it described as the new president's pattern of duplicitous behavior.
- Separated at Birth? (1988, ISBN 0-385-24744-3): A collection of photographs from "Separated at Birth?"
- Private Lives of Public Figures (Drew Friedman, cartoons from Spy, 1990)
- Spy Notes on McInerney's "Bright Lights, Big City"/Janowitz's "Slaves of New York"/Ellis's "Less Than Zero" and All Those Other Hip Urban Novels of the 1980s (1989, ISBN 0-385-24745-1): A CliffsNotes-style look at the literature of the nineteen-eighties
- Separated at Birth? 2: The Saga Continues (1990, ISBN 0-385-41099-9)
- Spy High (1992)
- George Kalogerakis, Kurt Andersen, and Graydon Carter, Spy: The Funny Years (2006, ISBN 1-4013-5239-1)
- Polly Vernon (24 October 2009). "Graydon Carter: Literati? Glitterati? I'd rather have a quiet night in with the missus…". The Guardian. Retrieved 25 July 2015.
- John Connolly (18 April 2010). "Steven Seagal Under Siege". The Daily Beast. Retrieved 25 March 2013.