Primarily a magazine of satirical journalism 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. It specialized in intelligent, thoroughly researched, irreverent pieces targeting the American media and entertainment industries. Some of its features attempted to present the darker side of celebrities such as Arnold Schwarzenegger, John F. Kennedy, Jr., Martha Stewart, and especially the real-estate tycoon Donald Trump and his then-wife Ivana Trump. Pejorative epithets of celebrities became a Spy trademark.
Spy briefly broke even in 1989, but was ultimately not successful as a business, particularly after a recession affected the U.S. economy beginning in the early 1990s. The founders sold the magazine to European buyers in 1991; several months later, Carter left the magazine; Andersen departed 18 months later, replaced by Tony Hendra. The magazine briefly ceased publication in 1994, was revived soon after under new ownership, and finally went out of business 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.
For a humorous magazine, Spy was often 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 lawyers to vet such potentially libelous material, but its stories often angered their prominent subjects, occasionally driving away advertisers.