Playboy (stylized in all caps) is an American men's lifestyle and entertainment magazine, available both online and in print. It was founded in Chicago in 1953 by Hugh Hefner and his associates, funded in part by a $1,000 loan from Hefner's mother.

Known for its centerfolds of nude and semi-nude models (Playmates), Playboy played an important role in the sexual revolution and remains one of the world's best-known brands, with a presence in nearly every medium. In addition to the flagship magazine in the United States, special nation-specific versions of Playboy are published worldwide, including those by licensees, such as Dirk Steenekamp's DHS Media Group.

The magazine has a long history of publishing short stories by novelists such as Arthur C. Clarke, Ian Fleming, Vladimir Nabokov, Saul Bellow, Chuck Palahniuk, P. G. Wodehouse, Roald Dahl, Haruki Murakami, and Margaret Atwood. With a regular display of full-page color cartoons, it became a showcase for cartoonists such as Jack Cole, Eldon Dedini, Jules Feiffer, Harvey Kurtzman, Shel Silverstein, Doug Sneyd, Erich Sokol, Roy Raymonde, Gahan Wilson, and Rowland B. Wilson. Art Paul designed the bunny logo. Leroy Neiman drew the Femlin characters for Playboy jokes. Patrick Nagel painted the headers for Playboy Forum and other sections.

Playboy features monthly interviews of public figures, such as artists, architects, economists, composers, conductors, film directors, journalists, novelists, playwrights, religious figures, politicians, athletes, and race car drivers. The magazine generally reflects a liberal editorial stance, although it often interviews conservative celebrities.

After a year-long removal of most nude photos in Playboy magazine, the March–April 2017 issue brought back nudity.

By spring 1953, Hugh Hefner—a 1949 University of Illinois psychology graduate who had worked in Chicago for Esquire magazine writing promotional copy; Publisher's Development Corporation in sales and marketing; and Children's Activities magazine as circulation promotions manager—had planned out the elements of his magazine, that he would call Stag Party. He formed HMH Publishing Corporation, and recruited his friend Eldon Sellers to find investors. Hefner eventually raised just over $8,000, including from his brother and mother. However, the publisher of an unrelated men's adventure magazine, Stag, contacted Hefner and informed him it would file suit to protect their trademark if he were to launch his magazine with that name. Hefner, his wife Millie, and Sellers met to seek a new name, considering "Top Hat", "Gentleman", "Sir'", "Satyr", "Pan", and "Bachelor" before Sellers suggested "Playboy".

Published in December 1953, the first issue was undated, as Hefner was unsure there would be a second. He produced it in his Hyde Park kitchen. The first centerfold was Marilyn Monroe, although the picture used initially was taken for a calendar rather than for Playboy. Hefner chose what he deemed the "sexiest" image, a previously unused nude study of Monroe stretched with an upraised arm on a red velvet background with closed eyes and mouth open. The heavy promotion centered on Monroe's nudity on the already-famous calendar, together with the teasers in marketing, made the new Playboy magazine a success. The first issue sold out in weeks. Known circulation was 53,991. The cover price was 50¢. Copies of the first issue in mint to near-mint condition sold for over $5,000 in 2002.

The novel Fahrenheit 451, by Ray Bradbury, was published in 1953 and serialized in the March, April and May 1954 issues of Playboy.