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13 of Playboy’s Best Halloween Cartoons

Cartoonist Gahan Wilson kept Playboy's funny pages spooky year-round.

Culture • October 31, 2026
13 of Playboy’s Best Halloween Cartoons

Playboy‘s cartoons are well-known for bordering on outrageous, but one of our longstanding cartoonist made sure our funny pages were downright spooky, too.

Gahan Wilson’s work spanned Playboy‘s pages for six decades, starting in 1958, when he sparked a relationship with the magazine’s founder after overhearing his commitment to keeping the publication “pro sin.” Before his death in 2019, Playboy had published more than 700 of Wilson’s cartoons, each of which sit between humor and horror.

On Halloween, we’re revisiting 13 of our favorite Wilson works to keep the spooky spirit alive.

“As I suspected — Mr. Harding, here, is possessed by demons.”

June 1974.

“To tell the truth, I wish this place hadn’t caught on with the werewolves.”

November 1980.

“Here comes your tomato surprise, sir.”

February 1988.

“I was just wondering, Mr. Parker, when you planned to come by and pick up Mrs. Parker?”

April 1995.

“They must be from a time when it was safe to meet in the park at night.”

November 1995.

“I see you’ve noticed my trophies!”

April 1996.

“No sacrifices until you buy the idol, sir.”

March 1997.

“The fangs stay!”

October 1997.

“…And there’s the fish that caught Henry!”

September 2010.

“I think it might be a good idea to avoid this one.”

November 2010.

“We’re doing everything we can for your husband, Mrs. Carter.”

August 2011.

“All right, count, let’s see that big, bright smile of yours!”

November 2011.

“Okay, you know what to do if they don’t give us candy.”

October 2014.

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