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The Wittiest Halloween Jokes, Riddles, and Puns

We fear vampires, and vampires fear tooth decay.

Grinning Halloween Lantern/Flickr
Source: Grinning Halloween Lantern/Flickr

Searching the Web for the very best Halloween humor has been a fun task—more than I could have imagined. I have to admit, though, that in my explorations I was obliged to wade through hundreds of really bad puns, which (with many a groan) I hastened to eliminate from consideration. But my detailed examination also yielded a great many delights. With surprised gratification, I learned, for example, that a vampire's favorite ice cream is veinilla (who would've thought?!) and that a ghost with a broken leg is called a "Hoblin Goblin."

As might be obvious, I take great enjoyment in all sorts of wordplay and creative punning. I also admire the cleverness of those anonymous individuals who feel free to make up new words simply for fun—as in one jokester who informs us that monsters can tell their future by reading their "horrorscope."

The liberty these modern-day jesters give themselves to celebrate this paradoxically dark, yet most whimsical, of holidays feels weirdly refreshing to me. After all, it is a time when adults can be kids again. In fact, Halloween parties for grown-ups may be just as common as those for children (possibly more so?).

As for the kids? Well, on this particular day they're given—or they take—the license to become (almost literally) the very creatures they previously may have most feared. And they're free to indulge in joyful silliness that's a lot less susceptible to parental criticism than otherwise might be the case. For this is a time when they can do things that ordinarily would be forbidden—or unthinkable: Like dressing up in outrageous (not to say, morbid) costumes and more or less demanding candy from strangers.

I still remember the year when I opened the door to some solitary ghoul and was (rather aggressively, I thought) greeted with the words "trick or treat!" A trifle annoyed by the coerciveness of his tone (and perhaps for the sake of experiment), I replied "trick!"—and was promptly squirted several times in the face with water from a concealed pistol. Who knew he'd actually come "armed"?! Still, on this special night of "licenses," I realized that this (to me) unruly child was quite within his rights. So I really had no choice but to wipe off my face and reach for the bowl of miniature Hershey bars.

Before presenting you with what I regard as the very best examples of Halloween foolery (or, well, lunacy), let me suggest something about how I chose these particular witticisms. In most instances, I had to distinguish between that which seemed (to whatever extent) forced, trite, or cornball, from what in my estimation appeared genuinely fresh, imaginative, or clever. And on many occasions, only a thin line appeared to separate the two. Most puns on the margin I rejected, though some did make the cut (though just marginally). "What did the boy ghost say to the girl ghost? ‘You look boo-tiful tonight.'" was relatively easy to cut—just too strained. But "What do birds give out on Halloween night?"—the answer being "tweets"—was, to my mind, cute enough to include (i.e., slightly shy of cutesy). . . . But what would you have decided?

Here are the finalists.

On Halloween, parents send their kids out looking like me. [And, if so, no wonder he never got any respect!] ~ Rodney Dangerfield

Halloween was confusing. All my life my parents said, "Never take candy from strangers." And then they dressed me up and said, "Go beg for it." I didn't know what to do. I'd knock on people's doors and say, "Trick or treat. No, thank you." ~ Rita Rudner

This Halloween the most popular mask is the Arnold Schwarzenegger mask. And the best part? With a mouth full of candy you will sound just like him. ~ Conan O'Brien

I dressed up as a veterinarian for a Halloween costume party. I had a lab coat. And I got a couple of stuffed animals for patients and put bandages on them. ~ Tracy Chapman

A grandmother pretends she doesn't know who you are on Halloween. ~ Erma Bombeck

Demons are a ghoul's best friend. ~ Anon

Being in a band you can wear whatever you want--it's like an excuse for Halloween everyday. ~ Gwen Stefani

Acting is like a Halloween mask that you put on. ~ River Phoenix

Halloween is the one night a year when girls can dress like a total slut and no other girls can say anything about it. ~ Lindsay Lohan

Eat, drink and be scary. ~ Anon

May your every wish be granted. ~ Ancient Chinese Curse [okay, doesn't quite fit but—just for fun—I couldn't resist throwing it in]

May your left ear wither and fall into your right pocket. ~ Arab Curse [ditto]

There are three things I have learned never to discuss with people: religion, politics and the Great Pumpkin. ~ Linus Van Pelt in "It's the Great Pumpkin, Charlie Brown"

© 2011 Leon F. Seltzer, Ph.D. All Rights Reserved.

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