Smiley Faces

From their first appearance over 40 years ago to their popularity as emoticons, the Smiley Face has become incredibly popular. Here are some smiley faces you can try on your pumpkins.

All Smiley patterns involve scraping for the border of the smiley if for nothing else. As a result all smiley patterns start at intermediate.

Print Pattern

INTERMEDIATE

The Smiley Face

Intermediate

The smiley face! A staple of the 1970s resurrected for emoticons today. Smile! Be happy! :)
Print Pattern

The Winky

Intermediate

While the first of the modern emoticons was the smiley, the winky was next. We all have something a little tongue in cheek to say sometimes, right? ;)
Print Pattern

The Sad Smiley

Intermediate

Everyone feels a little down from time to time. :(
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The Depressed Smiley

Intermediate

This is beyond sad. This is country music sad. Epic sad.
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The Shocked Smiley

Intermediate

Shocked, surprised or aghast, this smiley will always find you unexpected. :O
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Oh No! Smiley

Intermediate

Oops! Shouldn't have done that! :o
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The Freckled Smiley

Intermediate

It's a curse! They always come out more in the summer.
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The Scared Smiley

Intermediate

Zoinks! Any more scared and this smiley will pass out.
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The Screaming Smiley

Intermediate

More reality TV?
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The Widows Peak Smiley

Intermediate

Now this is style!
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The Howling Smiley

Intermediate

Wow! Party animal!
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The Evil Smiley

Intermediate

The smiley's evil twin! Here to raise Caine while he is Abel.
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The Evil Grin Smiley

Intermediate

This smiley is up to something!
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The Sleepy Smiley

Intermediate


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The Confused Smiley

Intermediate

What's going on?
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The Crying Smiley

Intermediate

Woebegone Smiley. Poor thing.
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The Anime Smiley

Intermediate

The smiley from Japan!
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The Pirate Smiley

Intermediate

What's the letter before 'S'? Arrrrrrrr!
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The Potter Smiley

Intermediate

This ain't no muggle.
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The Voldemort Smiley

Intermediate

Want to hear a Riddle? Lord Voldemort.
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The Vampire Smiley

Intermediate

This smiley isn't just Evil, it wants to suck your blood!
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The Walrus Smiley

Intermediate

Not a vampire and not Jamie Hyneman of Mythbusters, this is a walrus smiley.
Print Pattern

The Concentrating Smiley

Intermediate

Focus... Think...
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The Raised Eyebrow Smiley

Intermediate

You think Smiley patterns are too hard for you to carve. Really?
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The Pumpkin Smiley

Intermediate

He's all ready for Halloween!
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The Cross-Eyed Smiley

Intermediate

Clearly he's looking for his missing nose.
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The Eye Roll Smiley

Intermediate

Tired of all the fuss, are we?
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The Grinning Smiley

Intermediate

We're popular and we know it!
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The Disappointed Smiley

Intermediate

Not quite sad, but I'm sure we'll get there if the disappointment continues...
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The Cyclops Smiley

Intermediate

He's here to keep an eye on you.
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The Smirking Smiley

Intermediate

This smiley is good and she knows it!
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The Crazy Smiley

Intermediate

It's crazy! Crazy about being on this page, that is.
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The Lazy-Eyed Smiley

Intermediate

Wow! That one eye's got a mind of its own.
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The Grey Alien Smiley

Intermediate

Can you give me directions to Roswell?
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Saint Smiley

Intermediate

Call the Vatican!
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The Devil Smiley

Intermediate

Evil! Horned evil!
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The Alien Smiley

Intermediate

From beyond the Solar System!
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The Ghost Smiley

Intermediate

Dying to be carved by you!
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The Bizarro Dream Smiley

Intermediate

Wavy, twisted and not altogether normal, that's what this smiley is.
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The Spider Smiley

Intermediate

He's got his eyes on you.
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The Paranoid Smiley

Intermediate

This Smiley has discovered that just because it's paranoid doesn't mean that something isn't out to get it.
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The Super Smiley

Intermediate

The last smiley of a dead planet sent to Earth as a smile ambassador!
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The Wonder Smiley

Intermediate

This one's a real princess. She and the previous smiley are super friends.
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The Valentine Smiley

Intermediate

You won't just love this smiley, it will love you back!
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The Shamrock Smiley

Intermediate

When Irish eyes are smiling!
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The Canada Day Smiley

Intermediate

A Canadian smiley, eh?
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The Independence Day Smiley

Intermediate

He's a yankee doodle smiley.
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The Unibrow Smiley

Intermediate

Desperately seeking a razor and some wax.
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The Smiley in Profile

Intermediate

He doesn't seem to think this is his good side.
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The Granny Smiley

Intermediate

You love your granny, don't you?
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The Triangle Smiley

Intermediate

A new angle on an old theme.
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The Square Smiley

Intermediate

This smiley is a real square.
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The Cubic Smiley

Intermediate

And now the conversion to no curves is complete!
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The Yummy Smiley

Intermediate

Oh man, that was delicious!
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The Yummy Smiley II

Intermediate

Yum! The best candy!
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The Yuck Smiley

Intermediate

Ewww! Poison? No! Sour candies!
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The Doctor Smiley

Intermediate

Nobody uses the headband anymore, but our Smiley is a traditionalist.
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Robosmiley

Intermediate

Smile, or there will be trouble.
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The Real Eye Smiley

Intermediate

This one has real eyes. Spooky!
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The Real Nose Smiley

Intermediate

And now a real nose? All the better to smell us with???
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The Tired Smiley

Intermediate

Smiley is just bagged.
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The Fainting Smiley

Intermediate

I guess that the excitement of Halloween coming was too much for Smiley... He's fainted!
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The Greedy Smiley

Intermediate

Look out for your wallets! This smiley has dollar signs in his eyes!
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Beard Stubble Smiley

Intermediate

Is he cool or is he just lazy? Only Don Johnson knows for sure!
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The Stoned Smiley

Intermediate

Right out of the 70's, it's the stoned smiley!
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The Heart Smiley

Intermediate

All you need is love!
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The Peace Smiley

Intermediate

Ban the bomb! Give peace a chance!
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Target Smiley!

Intermediate

Secret agent? Hapless victim? Maybe someone just doesn't like smilies?
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Eyes In The Dark Smiley

Intermediate

Look out! Smiley has been possessed by the Eyes in the Dark!
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Smiley With A Monocle

Intermediate

Vision a little off in one eye only? Ever consider a monocle?
Print Pattern

The Frustrated Smiley

Intermediate

Oooooooo! I messed up that carving again.
Print Pattern

The Yawning Smiley

Intermediate

Bored now.
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The Shouting Smiley

Intermediate

CARVE ME!
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The Angry Smiley

Intermediate

Oh oh! What did we do?
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The Proud Smiley

Intermediate

Smug? Self-satisfied? No. Merely proud about a job well done!
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The Unimpressed Smiley

Intermediate

Wow. You carved a smiley face. Colour me underwhelmed. (This in no way represents the opinion of Pumpkin Jack. Make the effort and carve it!)
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Father Smiley

Intermediate

...or maybe Reverend Smiley.
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Iron Smiley

Intermediate

He's not invicible...
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The Egg Smiley

Intermediate

Sometimes I'm everything I'm cracked up to be!
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The Singing Smiley

Intermediate

Ah! Smiley is singing his little heart out!
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Teenage Mutant Ninja Smiley

Intermediate

Cowabunga!
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The Scarred Smiley

Intermediate

Scars are cool. They make me look manly. Chicks dig scars.
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The Snake Smiley

Intermediate

Don't make be angry or you will be hisssstory.
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Ouch!

Intermediate

Now that hurt!!!
Print Pattern

ADVANCED

The Mrs Smiley

Advanced

This is Smiley's wife. She seems just as happy about it.
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The Tongue Smiley

Advanced

Nyah-nyah-nyah-na-nyah-nyah!
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The Homina Homina Smiley

Advanced

Smiley just saw his wife...right?
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King Smiley

Advanced

The Lord of the Smileys.
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The Guilty Smiley

Advanced

Oooooo, what I did!
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The Sick Smiley

Advanced

I'm not feeling well. I think I'm going to...
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The Teeth Baring Smiley

Advanced

Wow, is he angry!
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The Cool Smiley

Advanced

Wearing glasses without a nose isn't easy, but once you've got it mastered, it's easy to be cool.
Print Pattern

The Embarrassed Smiley

Advanced

I think this one has trouble appearing here. Move on to the next smiley quickly.
Print Pattern

The Kissing Smiley

Advanced

Watch out! It might kiss you!
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The Party Smiley

Advanced

Party Smiley is in the house tonight!
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The Witch Smiley

Advanced

The witch smiley is going to cast a spell on you!
Print Pattern

The LOL Smiley

Advanced

Well, someone must have told a good joke!
Print Pattern

The Unicorn Smiley

Advanced

Look who's horning in on this page.
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The Shark Smiley

Advanced

This one would be happy to take a bite out of you!
Print Pattern

A Smiley with Piercings

Advanced

Piercings? Through the lip. Through the eyebrow. Through the nose. Nose?
Print Pattern

The Jolly Smiley

Advanced

Yo ho!
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Robot Smiley

Advanced

Smiling is illogical.
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Mr. S!

Advanced

I pity the fool that doesn't like Mr. S.
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The Moustached Smiley

Advanced

A nice stylish moustache!
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The Landlord Smiley

Advanced

You forget the rent. Bwahahaha!
Print Pattern

The Bearded Smiley

Advanced

Does this make the smiley look sinister?
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The Bow Tie Smiley

Advanced

Bow ties are cool!
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The Fez Smiley

Advanced

And fezes are also cool!
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The Hitler Smiley

Advanced

Nearly 70 years since his death and he can still invoke hatred, loathing and fear. One of the ultimate human embodiments of evil, I'm not surprised I've never seen a picture of Hitler smiling.
Print Pattern

The Cat Smiley

Advanced

Meow!
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The Klingon Smiley

Advanced

Are you a weak Federation Smiley?
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The Ultra-Brain Smiley

Advanced

This one could make your brain explode...but it wouldn't because it is so friendly.
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The Steampunk Smiley

Advanced

My goggles are the only gear I need.
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The Scuba Smiley

Advanced

Under the sea is where this smiley will be.
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The Facepaint Smiley

Advanced

Yeh flower power!
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The Brawling Smiley

Advanced

Ah! The good old hockey game!
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The Balaclava Smiley

Advanced

Is it cold or does Smiley not want you to know who he is?
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The Moose Smiley

Advanced

This smiley thinks it is a moose. Hmmm.
Print Pattern

The Bird Smiley

Advanced

And this smiley thinks it is a bird! Wait, is that beak real?
Print Pattern

The Ant Smiley

Advanced

Now where is that rubber tree plant? I've got high hopes!
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Old Smiley Eyes

Advanced

Okay, this is just creepy.
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The Creepy Eyed Smiley

Advanced

And this is even more creepy!
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The Beholder Smiley

Advanced

Carving is in the eye of the beholder.
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The Pope Smiley

Advanced

Holy Smiley!
Print Pattern

The Mountie Smiley

Advanced

He always gets his smiley!
Print Pattern

The Sherlock Smiley

Advanced

When you have eliminated the impossible smileys, whatever smiley remains, however improbable, must be the smiley.
Print Pattern

The Headphone Smiley

Advanced

Smiley is happy. He is listening to his tunes!
Print Pattern

The Vaudeville Smiley

Advanced

So what's smiley up to? Song and dance? Comedy? Introducing an act?
Print Pattern

Way Too Much Snow Smiley

Advanced

Oh no! Smiley is buried in snow!
Print Pattern

The Cylon Smiley

Advanced

How am I to kill Colonial Warriors when I only have one eye that goes back and forth and back and forth and back and forth and ...
Print Pattern

The Luchador Smiley

Advanced

Why is he smiling. Wearing that mask all day is HOT!
Print Pattern

The Bat Smiley

Advanced.

I'm Bat Smiley.
Print Pattern

The Ninja Smiley

Advanced

Ha! Snuck this one past you!
Print Pattern

The Wild Toothy Grin Smiley

Advanced

Wow! Imagine his dental bill!
Print Pattern

The Nurse Smiley

Advanced

Notice the smiley's classic nurse's cap. Pretty cool to be retro!
Print Pattern

The Sailor Smiley

Advanced

Ahoy!
Print Pattern

The Flower Child Smiley

Advanced

Flower power! Well Smiley is a child of the hippy era.
Print Pattern

The Smoking Smiley

Advanced

** Pumpkin Jack Public Service **

Poor Smiley! He thought smoking would be cool. It costs him a fortune, he has to leave his friends when they are out for the night to go have a smoke, he smells bad, he coughs constantly now and he has tried to quit three times now without success. He wishes he had never started smoking in the first place.


Print Pattern

EXPERT

The Bandana Smiley

Expert

Is he a pirate? A hippy? You decide.
Print Pattern

The Braces Smiley

Expert

Just think of how beautiful its teeth will be...I didn't think Smilies had teeth...
Print Pattern

The Hooded Smiley

Expert

Robbing from the rich and giving to the poor?
Print Pattern

The Medieval Smiley

Expert

This one will go medieval on you.
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The Viking Smiley

Expert

By Odin's beard, he will plunder smiles.
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The Cowboy Smiley

Expert

Yippie Kai Yai! Yee Haw! Ride 'em smiley!
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The Chef Smiley

Expert

Now this one is really cooking!
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The Ballcap Smiley

Expert

Batter up!
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The Top Hat Smiley

Expert

I say, good person, wouldn't you like to carve me on a pumpkin this Halloween?
Print Pattern

Smiley with a Toque

Expert

Love the pom pom! I guess it's cold.
Print Pattern

The Bowler Hat Smiley

Expert

What style! Is he Steed? Is he Oddjob? Maybe he's a steampunker!
Print Pattern

The Leprechaun Smiley

Expert

I wonder if he has a pot of gold?
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The Police Smiley

Expert

Upholding the smiley law!
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The Hard Hat Smiley

Expert

This smiley knows how to be safe.
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The Cthulhu Smiley

Expert

Don't go crazy carving this one!
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The Santa Smiley

Expert

Ho ho ho!
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The Bunny Smiley

Expert

The Easter Smiley? A Vorpal Bunny? Smilies, smilies, it must be smilies?
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The Egyptian Smiley

Expert

From out of the sands of time comes this ancient smiley.
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The Terminator Smiley

Expert

I'm back! Are you Sarah Conor?
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The Punker Smiley

Expert

Boy is he tough!
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The Masked Smiley

Expert

Who is that masked smiley?
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Darth Smiley

Expert

A Smiley with asthma and a deep understanding of the Force.
Print Pattern

The Dalek Smiley

Expert

I would be happy to exterminate you!
Print Pattern

The Cyberman Smiley

Expert

Submit to pumpkin carving or be deleted!
Print Pattern

The Sontaran Smiley

Expert

The residence is under attack by disguised immature humans. Perhaps a grenade or two might help.
Print Pattern

The Scarf Smiley

Expert

What an interesting scarf! And he keeps offering people something called "jelly babies".
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Frankensteins Smiley

Expert

If Dr. Frankenstein had his own smiley, this would be it.
Print Pattern

Indiana Smiley

Expert

Indiana Smiley and The Raiders of the Lost Emoticons.
Print Pattern

The Space Smiley

Expert

To the Moon!
Print Pattern

The Clown Smiley

Expert

Some people are afraid of clowns, but how can you be afraid of this little smiley?
Print Pattern

The Zombie Smiley

Expert

Brains!
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The Flaming Smiley

Expert

This smiley's on fire!
Print Pattern

The Mummy Smiley

Expert

All wrapped up and no place to go.
Print Pattern

The Ghoulish Smiley

Expert

You look good. Delicious in fact.
Print Pattern

The Borg Smiley

Expert

Resistance is futile. You will be assimilated. Carving is inevitable.
Print Pattern

Firefighter Smiley

Expert

An extinguished smiley!
Print Pattern

The Camoflage Smiley

Expert

He thinks this will help him blend in in the jungle...the urban jungle!
Print Pattern

The Reindeer Smiley

Expert

Is Santa missing a reindeer? No, wait, that's Smiley.
Print Pattern

The Smiley Wearing a Bicycle Helmet

Expert

Saftey first!
Print Pattern

The Conductor Smiley

Expert

All aboard!
Print Pattern

The Killer Plant Smiley

Expert

Feed me!
Print Pattern

The Lawyer Smiley

Expert

Wait until you see my fees!

As a sidebar, we at Pumpkinjack have the highest respect for those in the legal profession. Keep smiling!


Print Pattern

The Xenomorph Smiley

Expert

In space, no one can hear you smile.
Print Pattern

The Inner Sight Smiley

Expert

Are those eyes in there? Why don't you take a closer look?
Print Pattern

The Football Smiley

Expert

Touchdown!
Print Pattern

The Baby Smiley

Expert

Awwww! Isn't it cute?
Print Pattern

The Beret Smiley

Expert

Zis is da French Smiley, oui?
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The Army Smiley

Expert

Smiley's in the military?
Print Pattern

The Jester Smiley

Expert

This smiley is a jester. He can't fool us.
Print Pattern

The Sombrero Smiley

Expert

Is this the sombrero Smiley? Si!
Print Pattern

The Jolly Smiley

Expert

Yes, this is the full Santa! Before we only had Smiley in a hat.
Print Pattern

The Frozen Smiley

Expert

Smiley just survived an ice storm, then went through a deep chill arctic vortex. Poor Smiley!
Print Pattern

The Blues Brother Smiley

Expert

This is the 4th brother...Smiley.
Print Pattern

KISS Smileys

The Demon

Expert

That's makeup, right?
Print Pattern

The Star Child

Expert

He's a fan of 2001: A Space Odyssey.
Print Pattern

The Space Man

Expert

This one smiles Frehley.
Print Pattern

The Cat Man

Expert

Meow!
Print Pattern

Four Fantastic Smileys

The Invisible Smiley

Expert

Now you see her, now you don't.
Print Pattern

The Smiley Thing

Expert

Don't be so Grimm. Rock on dude!
Print Pattern

Smiley Fantastic

Expert

Sorry, reaching a bit with this one.
Print Pattern

The Smiley Torch

Expert

Burnin' down the house!