Sex & Relationships
Playboy Undercover: The Almost 40-Year-Old Virgin "I am 38 and I still haven’t had my first kiss yet—which means yes.… I am a virgin too."
For decades, Playboy readers have been getting jiggy with the world's sexiest puzzles
For Playboy’s September 1960 cover, featuring Playboy Bunny Marli Renfro, art director Art Paul worked with a puzzle maker to create a one-of-a-kind jigsaw out of Don Bronstein’s photo.
That unique cover paved the way for actual Playboy puzzles later that decade. Toward the end of the swinging 1960s, Playboy began publishing puzzle versions of magazine Centerfolds. Over the next three decades, dozens of Playmates, including DeDe Lind, Gwen Wong and Marilyn Cole were featured on puzzles. From regular-size 300– to 500-piece puzzles to life-size 150-piece versions, the puzzles were a hit.
The puzzles became popular with fans and collectors. The famous resident of the Playboy Mansion was not immune to the charming games either: Hugh Hefner displayed them in the hallways and stairways of his home.
Longtime puzzlers and those looking for a pandemic pastime, rejoice! To honor its history with puzzles, Playboy chose two special covers (neither of which has ever been used for a puzzle before) and turned them into limited-edition puzzles. Like all Playboy covers, each has a unique story that might surprise you—or at least help you during Playboy trivia night. The backstories won’t make completing these brainteasers any easier, but they may just provide the missing piece that makes finishing them all the more satisfying.

For Playboy’s 20th anniversary issue, the creative team decided on a simple but classic cover design by Len Willis that highlighted the intricacies of the famed Rabbit Head logo. (Many bootleggers and knockoff artists have tried replicating the recognizable bow-tied bunny on fake merch, only to realize the icon is far more complex than they initially realized.) With photography by Dwight Hooker and some choice hand-modeling from February 1973 Playmate and 1974 Playmate of the Year Cyndi Wood, the cover welcomes readers to an issue full of fine journalism, including a Playboy Interview with Hugh Hefner himself.

This cheeky cover, featuring model Eva Maria (who was later photographed by Pompeo Posar for the December 1976 issue), was designed by then-associate art director Tom Staebler and photographed by Posar to promote a playful magazine pictorial called *Ripped Off.* Featuring work from seven photographers, the sensual nine-page piece shows lovers ripping up or tearing off various items while in the throes of lust—sheets, lingerie, panties, plastic wrap, wigs and even a mustache. If the opposite passion grabs you and you find yourself in the mood to put things together rather than tear them apart, we highly we highly recommend sitting down for some puzzle pleasure.