Valentine’s Day, the Vintage Playboy Way

Twelve cartoons from the archives that are bound to make you blush, or laugh (or both).

Entertainment & Culture February 14, 2026
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Valentine’s Day is for lovers, and in this case it’s for lovers of a good laugh. The romance holiday has always been a big one for Playboy, featuring steamy pictorials, full-book reflections on attraction and desire, and, of course, cartoons. From the droll to the skeptical to the downright quirky, these cartoons capture the silly side of not just love and sex, but the holiday itself.

Enjoy a few funnies from Playboy‘s archives to celebrate this Valentine’s Day.

“There they are again!” Michael Folks, 1971
Smilby, 1989
“To my valentine, Brad, with all my love, Betty.” Rick Stromoski, 1994
John Dempsey, 1987
“Safe sex, you know.” Peter Kohlsaat, 1994
Alden Erikson, 1996
“For us it was a case of love at first sighting.” Glenn McCoy, 1996
Mort Gerberg, 1996
“This is our latest. A combination love-and-hate potion. Very sophisticated.” Ed Fisher, 1996
Mort Gerberg, 1982
“Look, kid, from now on just shoot your arrows – then bug out!” Art Krusz, 1966
Michael Maslin, 1998

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