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|Editor||Graydon Carter and Kurt Andersen|
|Based in||New York City|
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", "short-fingered vulgarian Donald Trump", "churlish dwarf billionaire Laurence Tisch", "bum-kissing toady Arthur Gelb", "bosomy dirty-book writer Shirley Lord" and "former fat girl Dianne Brill" became a Spy trademark.
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.
Introduced in the May 1987 issue, Private Lives of Public Enemies (renamed Private Lives of Public Figures, then simply Private Lives in 1989) presented fictional representations of public personalities in unflattering situations.
Separated at Birth?, first presented in a feature article in December 1987, was a regular section which would present juxtaposed photos of two different personalities exhibiting visual similarity, to comical effect. The first of each pair was typically a public figure or celebrity, and the second was usually another such figure, but sometimes (usually in the last set) a more absurd subject such as a fictional character, animal, or inanimate object. Separated at Birth? became one the magazine's most popular features and was spun out into a set of paperback books.
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.
- 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)
- "Spy Magazine (1986-1998) Now Online". Open Culture. 28 April 2011. Retrieved 8 December 2015.
- Jeremy Glass (24 November 2014). "5 Defunct Magazines that Changed America". Thrillist. Retrieved 1 May 2016.
- Will Hines (27 April 2011). "Diving Into the Archives of Spy, The Funniest Magazine Ever". Split Sider. Retrieved 8 December 2015.
- 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.
- "Decades Later, 'Spy' Magazine Founders Continue To Torment Trump". npr.org. NPR. March 7, 2016. Retrieved August 6, 2016.
- "Datebook". Spy Magazine. Spy Publishing Partners L.P. (February 1988): 20. ISSN 0890-1759.
- "Spy". Google Books. July–August 1992. ISSN 0890-1759. Retrieved 8 December 2015.
- "Spy". Google Books. May 1993. ISSN 0890-1759. Retrieved 8 December 2015.
- "SPY on Esquire".