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Spy was a satirical monthly magazine founded in 1986 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. Spy was named after the fictitious magazine that employed James Stewart's character, Macaulay "Mike" Connor, in the movie The Philadelphia Story.
Primarily a magazine of satirical reporting and humor, but also featuring some more serious investigative journalism, the New York–based Spy traced its influences to "H. L. Mencken and A. J. Liebling and Wolcott Gibbs from the '20s, '30s, and '40s; parody-Time-ese of the '40s and '50s; New Journalism of the '60s and '70s; Private Eye, the scabrous (and much jokier) British fortnightly; and the ways we just happened to write," as Andersen and Carter would later write in Spy: The Funny Years. On April 12, 2011, during a live interview on Public Broadcasting Service (PBS), Kurt Anderson stated that Mad magazine also had a strong influence on their humor by creating examples of satirical and cold analysis of government and prominent figures read in their youth.
It specialized in intelligent, thoroughly researched, irreverent pieces targeting the American media and entertainment industries. 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.
"It's pretty safe to say," Dave Eggers wrote in 2006, "that Spy was the most influential magazine of the 1980s. It might have remade New York's cultural landscape; it definitely changed the whole tone of magazine journalism. It was cruel, brilliant, beautifully written and perfectly designed, and feared by all. There's no magazine I know of that's so continually referenced, held up as a benchmark, and whose demise is so lamented."
Despite its relatively short life, Spy was among the most widely acclaimed and discussed of American magazines of its time, chiefly for its detached and ironic tone, its use of quasi-scientific charts and tables to convey information, and its elaborate, classically influenced typography and layout.
With a business staff led by Phillips, founding advertising director and future Nickelodeon worldwide creative director Anne Kreamer, and future ESPN.com and Newsweek digital SVP Geoff Reiss, Spy broke even in 1989 and 1990. But it was not able to remain profitable after a recession began to affect the U.S. economy beginning in the early 1990s. The founders sold the magazine to advertising mogul Charles Saatchi and art collector Jean Pigozzi in 1991; several months later, Carter left the magazine; Andersen departed eighteen months later, being replaced by Tony Hendra. The magazine briefly ceased publication in 1994, was revived soon afterward under new ownership, and finally went out of business permanently in 1998. Its last editor was a recent Harvard graduate, Bruno Maddox.
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.
Spy's popular features included "Separated at birth?" (side-by-side photographs of two different celebrities, similar to Private Eye's "Lookalikes") and "Celebrity Math", which presented thumbnail head shots atop simple mathematical models representing the components of celebrities (e.g., Fabio - Catherine Deneuve = Billy Ray Cyrus).
The magazine also specialized in often elaborate stings and hoaxes that explored the American phenomenon of celebrity. Notable efforts in this regard include: the purchasing by the magazine of a bona fide Scottish noble title, a test of the U.S. Postal Service in which letters were addressed only with the photograph of the intended recipient (the letter sent to Cardinal John Joseph O'Connor was successfully delivered), and, to test the ethical limits of the public relations industry, the successful pitching of a chain of fast-food restaurants that served burgers of freshly ground rabbit meat and was fronted by a fuzzy-eared mascot who told customers how delicious his species was to humans.
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 alleged 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. After O.J. Simpson was acquitted on charges of murdering his former wife and her friend, Spy ran a cover story under the headline "He's Guilty, By George!" presenting a long list of details that its writers said proved conclusively that Simpson was the killer; he did not sue. The cover illustration parodied that of the much-hyped premiere issue of George magazine, with Simpson standing in for Cindy Crawford. Spy used attorneys to vet such potentially libelous material, but its stories often angered their prominent subjects and occasionally drove away advertisers.
Editorial staff 
- Kurt Andersen, co-founder
- Sonda Andersson, associate art director
- Graydon Carter, co-founder
- Alexander Isley, art director (1987–1988)
- Bruno Maddox, editor-in-chief (1996–1998)
- William Monahan, editor (1997–1998)
- John Norton, Advertising and Marketing Director (1987–1988)
- Henry Alford
- Aimee Bell
- Lisa Birnbach
- David Bourgeois
- Daniel Carter
- Jim Collins
- John Connolly
- Larry Doyle
- Josh Gillette
- Joanne Gruber
- Michael Hainey
- Bruce Handy
- B. W. Honeycutt
- George Kalogerakis
- David Kamp
- Walter Kirn
- Christian Kuypers
- Tim Long
- Jamie Malanowski
- Walter Monheit™
- Susan Morrison
- Cleo Paskal
- Daniel Radosh
- Paul Rudnick
- Elissa Schappell
- Nell Scovell
- Louis Theroux
- Anne Williamson
- 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 Presents: Spy Music (Vol I)
- Spy Magazine Presents: White Men Can't Wrap (Vol II)
- Spy Magazine Presents: Soft, Safe & Sanitized (Vol III)
See also 
- John Connolly (18 April 2010). "Steven Seagal Under Siege". The Daily Beast. Retrieved 25 March 2013.
- Dave Eggers (10 February 2011). "Spy". Google Books. Retrieved 12 May 2013.
- Spy magazine at Google Books
- Peter Hall, “Spy Magazine – 1986: Years after its demise the legendary magazine continues to exert a cultural influence,” Metropolis, April 2006 Issue, March 20, 2006
- Todd Leopold, “Spy magazine remembers ‘The Funny Years,’ ” CNN, November 16, 2006
- Ten Years Ago in Spy (retrospective site)
- "MONHEIT DEAD! Remembering Spy Magazine’s Elegant Blurbist, Messenger, and Nightclubber Extraordinaire"