The Best Playboy Holiday Covers of All Time

By Brian Fairbanks

Playboy has never known what to do about the holidays. Each year, the magazine recycles jokes our grandfather learned in The Great War about Santa Claus coming down the chimney and joining the orgy around the Christmas tree. They usually have Santa looking in on Eliot Spitzer and Ashley Dupre, saying, "Ho ho ho!" But once in a while, the magazine gets the holidays right: dressing up the Playmates as young Mrs. Clauses, complete with lingerie and a present in the bedroom, if we would just follow their come-hither looks.

January 1954. Playboy was a tad on the late side for its holiday cover that season, but maybe because the December '53 issue was its first ... and featured Marilyn Monroe on the cover. While the follow-up isn't quite as memorable as the premiere, it still demands a place on this list for featuring the Playboy Bunny character gleefully eyeballing a pair of boobs.


December 1960. While it took Playboy a few years to find the courage to combine eroticism and Christmas (and this was before the days when Bill O'Reilly would have have thrown a temper tantrum over it), the last cover of the first year of the swingin' 60s was at least a step forward. Sadly forgotten model Teddi Smith is shown standing up in her finest sexy Santa suit, and that's all she needs to do to sell us on this issue: stand there.


February 1970. This one's cheating a bit, but we missed it on our Best Playboy Covers of the 1970s list. Sure, February is a bit past the holiday season, but it probably went out to subscribers right after New Year's and has a Valentine's Day theme, so that counts, right? None of that matters, anyway, when there is a naked ass to enjoy.


December 1970. Who would have guessed that a naked model in a Santa hat would be sexier than just a plain ol' naked model? Shay Knuth knew this before we did, and thankfully Playboy gave her to us for Christmas in 1970.



December 1972. As the rest of the country joined the sexual revolution that Playboy helped jump-start, the magazine decided to buck the trend and step back into the past with its December '72 edition. The cover featured a play on the classic Coca-Cola Christmas ads, except with an illustration of a hot naked chick playing Santa Claus. The only way you'll ever get to see anything like this nowadays is by joining us at Santacon.


December 1974. Mother of God, what is Playmate Robyn Douglass going to do with that candy cane? The outrage, the scandal, the sacrilege! I'll take two copies, please.


January 1976. We'll give you 12 reasons why this cover makes our list: Lynnda Kimball, Mesina Miller, Lillian Müller (Yuliis Ruval), Azizi Johari, Ingeborg Sorensen, Victoria Cunningham, Lynn Schiller, Laura Misch, Jill de Vries, Bridgett Rollins, Janet Lupo, Nancie Li Brandi. One for every lonely night of Christmas.


January 1993. Four boobs, one cover. You would be forgiven for having high expectations for 1993 after receiving this in your mailbox.


December 1996: Playboy's holiday covers bounced back in a big way in '96 with this Jenny McCarthy-led edition -- you know, before she was spoiled by Jim Carrey.


December 1999. As awful as Naomi Campbell's outfit is on the cover of Playboy's 1999 holiday issue, the supermodel at least had the hotness to make it work. But ... hang on a second ... isn't a landline phone what Ms. Campbell launched at her assistant that one time?


December 2000. This is exactly what you should get me for Christmas this year, Mom: a miniature naked Carmen Electra, trapped inside a tree ornament.