Playboy is a monthly magazine, founded in 1953 by Hugh Hefner and his associates and targeted at adult men. The magazine is published monthly and features photographs of nude women, along with various articles on fashion, sports, consumer goods, and public figures. It also has short fiction by top literary writers. Playboy's use of "tasteful" nude photos is often classified as "softcore" in contrast to the more "hardcore" pornographic magazines that started to appear in the 1970s in response to the success of Playboy's more explicit rival, Penthouse.
- In a 1966 presentation for La Choy, the magazine is featured during a Superman-esque introduction which claims that Delbert the La Choy Dragon is "sexier than Playboy."
- A copy of Playboy can also be seen on the conference table for a Wilson's Meats Meeting Film.
- Kermit's mansion in The Muppets is decorated with various magazine covers. One of them is a doctored cover of the Fall 1982 issue of Playboy Fashion with Kermit and Raquel Welch. Although the cover has been manipulated for the movie, the two did once share the actual cover of Us magazine in 1978.
- In a "Co-Star Challenge" video published by People on September 6, 2014, Pepe says that his favorite place to go for a swim is the grotto at the Playboy Mansion.
The comic feature Little Annie Fanny, created by Harvey Kurtzman and Will Elder, featured a Miss Piggy appearance in the Dec. 1983 issue's installment, "Little Annie Fanny's Workout Show." In 1998, the comic was revived with different artists for two issues, and again Miss Piggy appeared.
In 1989, Caroll Spinney told The Chicago Tribune about getting stopped by a friend at a newsstand who spotted him thumbing through an issue of Playboy and said, "Hey I didn't know Big Bird read those kinds of magazines." Spinney claimed to only be looking at it for the articles and replied, "I'm not Big Bird. I'm Caroll Spinney."
Several artists whose work has appeared in Muppet/Henson productions have also contributed to Playboy.
- Shel Silverstein contributed several travelogues, cartoons and poems to Playboy since its early days.
- Harvey Kurtzman created "Little Annie Fanny" comics in Playboy.
- Cliff Roberts contributed to Playboy.
- Dean Yeagle contributed cartoons to Playboy.
- The Chicago Tribune "The Brain Of Big Bird Talks About His 20-year Love Affair With A Famous Character" by Robert E. Sullivan Jr, November 14, 1989