Ghastly Halloween Greetings in the Ghoulish Days of Old (Second Edition)

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Last year, I did a post on crazy vintage Halloween cards that many wouldn’t believe existed. Sure you might think vintage artwork has a lot of cuteness and nostalgia filled images all over it. But there are plenty of vintage cards with imagery that seems kind of creepy or outright insane to modern eyes. Sometimes you’d think the old card companies hired people on acid to design them, which would explain a lot. And Halloween is no exception. Now this witch picture is a rather conventional vintage card image we’d expect from the holiday. Sure she’s on her broom with a jack-o-lantern on her stick and holding a cat. It’s hardly a remarkable image. Yet, if you want to see more like it, then this isn’t the place for you. But if you’re bored by traditional vintage Halloween cards and came for laughs, this is the place. So for your reading pleasure, I give you another treasure trove of crazy Halloween cards.

  1. “When you’re away on Halloween/The world seems then as dark/As lanterns, ere their candles feel/The match’s kindling spark.”
From I-Mockery: "I'm pretty sure that girl is about to get killed by Phanto. She must've stolen his key. (Yes, that's a geeky old video game reference. Deal with it.)" Don't like the looks of this.

From I-Mockery: “I’m pretty sure that girl is about to get killed by Phanto. She must’ve stolen his key.
(Yes, that’s a geeky old video game reference. Deal with it.)” Don’t like the looks of this.

2. “Good luck for Halloween.”

From I-Mockery: "If there's one thing this image doesn't make me feel, it's good luck. Fear the evil albino pumpkin lady." Thanks, lady with the demonic jack-o-lanterns, I'll keep that in mind.

From I-Mockery: “If there’s one thing this image doesn’t make me feel, it’s good luck.
Fear the evil albino pumpkin lady.” Thanks, lady with the demonic jack-o-lanterns, I’ll keep that in mind.

3. There’s no worse bad luck on Halloween than having your path crossed by a black cat.

Okay, did those pumpkin guys try to bake that cat in a cake? Or did the cat just pounce on it to scare the freaky pumpkin people away? At any rate, the cat has every right to be pissed.

Okay, did those pumpkin guys try to bake that cat in a cake? Or did the cat just pounce on it to scare the freaky pumpkin people away? At any rate, the cat has every right to be pissed.

4. Always have a jolly Halloween.

I think it would've been better if the kid just kept his pumpkin hat on. Because he's a walking racist stereotype. Of course, you must expect these things from vintage cards.

I think it would’ve been better if the kid just kept his pumpkin hat on. Because he’s a walking racist stereotype. Of course, you must expect these things from vintage cards.

5. Kids, remember to be safe this Halloween and watch out for creeping jack-o-lanterns during the night.

From I-Mockery: "I'm afraid. That's not even my house that the evil black pumpkinface is peering into, and I'm still afraid." Yeah, that's one of the scariest jack-o-lanterns I've seen here.

From I-Mockery: “I’m afraid. That’s not even my house that the evil black pumpkinface is peering into, and I’m still afraid.” Yeah, that’s one of the scariest jack-o-lanterns I’ve seen here.

6. The man in the moon always likes when witches come out at night, especially if they’re hot.

Yes, the man in the moon loves flying hot witches flying around with their form fitting dresses. This should tell us the that the man in the moon is a perv.

Yes, the man in the moon loves flying hot witches flying around with their form fitting dresses. This should tell us the that the man in the moon is a perv.

7. “If something scares you and you want to run/Remember it’s only Halloween fun!”

From I-Mockery: "Yeah, remember that advice when the creepy old man invites you into his home for some "extra special candy". Don't run, for it's only Halloween fun!" Also, that little kid is freaking me out. Really.

From I-Mockery: “Yeah, remember that advice when the creepy old man invites you into his home for some ‘extra special candy.’ Don’t run, for it’s only Halloween fun!” Note this is called sarcasm. Also, that little kid is freaking me out.

8. You never know what spell a witch may cast on Halloween night.

From I-Mockery: "Look! She's removing all the dust from her broom and putting it into that pie to feed everyone with! What a bwitch!"

From I-Mockery: “Look! She’s removing all the dust from her broom and putting it into that pie to feed everyone with! What a bwitch!”

9. On Halloween night, be nice to the jack-o-lantern driver and his cart or else.

From I-Mockery: "Remember what that other card said about not running away because it's just Halloween fun? Well, forget that shit. If you see this guy, run... run as fast and far away as you possibly can. If you don't he'll put you in his twisted traveling "pumpkin-man towed by a haunted billy goat" show."

From I-Mockery: “Remember what that other card said about not running away because it’s just Halloween fun? Well, forget that shit. If you see this guy, run… run as fast and far away as you possibly can. If you don’t he’ll put you in his twisted traveling ‘pumpkin-man towed by a haunted billy goat’ show.”

10. “Halloween Greetings! Good luck and good cheer/May these be the spirits that haunt you all year.”

From I-Mockery: "Are those two little guys actually supposed to be the spirits of "good luck" and "cheer"? I only ask because one of them looks like an annoying elf and the other looks like a depressed miniature grim reaper. Not exactly the kind of spirits you want visiting you all year long."

From I-Mockery: “Are those two little guys actually supposed to be the spirits of ‘good luck’ and ‘cheer?’ I only ask because one of them looks like an annoying elf and the other looks like a depressed miniature grim reaper. Not exactly the kind of spirits you want visiting you all year long.”

11. Halloween greetings from the children’s white sheet and jack-o-lantern cult.

Okay, I know those are supposed to be ghost costumes. But to me they seem like cult robes. The kids' sinister faces don't help either.

Okay, I know those are supposed to be ghost costumes. But to me they seem like cult robes. The kids’ sinister faces don’t help either.

12. Scary skeleton wraiths with lanterns wish you Halloween joy.

No, I don't think you'll find Frodo and his friends here. Also, why are dressed in white and carrying lanterns?

No, I don’t think you’ll find Frodo and his friends here. Also, why are dressed in white and carrying lanterns? And that’s no way to hold a cat comfortably.

13. May you have a Merry Halloween from the garden vegetable patch.

First, why do the veggies have arms and legs? And why does that radish seem waving to me? That's messed up.

First, why do the veggies have arms and legs? And why does that radish seem waving to me? That’s messed up.

14. When carving a pumpkin, make sure a pumpkin head ghost holds up a light.

Okay, scratch that. In fact, you might want to run like hell. Because that scary jack-o-lantern guy might want to kidnap you for a sacrifice with his friends. He really wants to impress them.

Okay, scratch that. In fact, you might want to run like hell. Because that scary jack-o-lantern guy might want to kidnap you for a sacrifice with his friends. He really wants to impress them.

15. Halloween is always a time for sharing dark secrets.

The girl is supposed to read this boy's fortune. But I think she's thinking of far more unspeakable evil things to do to him.

The girl is supposed to read this boy’s fortune. But I think she’s thinking of far more unspeakable evil things to do to him. That can’t be good.

16. Ladies, remember that mirrors aren’t always 100% on Halloween night.

From I-Mockery: "Popular witch prank: make somebody think they're a two-headed freak." Yes, kind of looks like it.

From I-Mockery: “Popular witch prank: make somebody think they’re a two-headed freak.” Yes, kind of looks like it.

17. Remember to wallop a black cat this Halloween, kids.

On second thought, that's just cruelty to animals. Best to wallop the kids in this card. Or the creepy pumpkin on the broomstick.

On second thought, that’s just cruelty to animals. Best to wallop the kids in this card. Or the creepy pumpkin on the broomstick. The cat only deserves your pity here.

18. Halloween greetings from the two zombie pumpkins in the patch.

From I-Mockery: "It's like those two zombie pumpkins are just daring the little boy and his dog to hop the fence and grab that healthy pumpkin. That's just downright horrifying."

From I-Mockery: “It’s like those two zombie pumpkins are just daring the little boy and his dog to hop the fence and grab that healthy pumpkin. That’s just downright horrifying.”

19. “Happy Halloween! You best be careful what you do/Jack-o-Lantern will catch you.”

From I-Mockery: "I could care less about the Jack-O-Lantern... I'm more concerned about what will happen if the two little demons catch me." Same here.

From I-Mockery: “I could care less about the Jack-O-Lantern… I’m more concerned about what will happen if the two little demons catch me.” Same here.

20. Happy Halloween from the jack-o-lamp post. Hope he doesn’t catch you making out.

From I-Mockery: "Sure, Jack O' Lantern caught them kissing, what with the lipstick on the man's face 'n all... but it also looks like he caught the guy copping a feel. Happy Halloween, fella!"

From I-Mockery: “Sure, Jack O’ Lantern caught them kissing, what with the lipstick on the man’s face ‘n all…but it also looks like he caught the guy copping a feel. Happy Halloween, fella!”

21. On Halloween, it’s best that pumpkin head people should be on alert for scraggly witches.

Because they tend to gang up on pumpkin people and do terrible things to them. I don't like where this is going.

Because they tend to gang up on pumpkin people and do terrible things to them. I don’t like where this is going.

22. I call this card, “Scenes from a Demonic Restaurant.”

It's where everything seems to come alive but in a way that will haunt your dreams forever. Also, the devil is in the details on the menu.

It’s where everything seems to come alive but in a way that will haunt your dreams forever. Also, the devil is in the details on the menu.

23. If you break up with someone on Halloween, chances are a ghost will haunt your dreams.

Now this is just terrible relationship advice. Because what if you break someone's heart because he was being a jerk? Shouldn't that be permissible.

Now this is just terrible relationship advice. Because what if you break someone’s heart because he was being a jerk? Shouldn’t that be permissible?

24. “Wish you a lucky Halloween.”

What the hell is Cupid doing here? He's in the wrong holiday card. Not to mention, who the hell has a room with floating apples and a pumpkin mirror?

What the hell is Cupid doing here? He’s in the wrong holiday card. Not to mention, who the hell has a room with floating apples and a pumpkin mirror?

25. Not all jack-o-lanterns are creepy. Some can be especially helpful with finding lost animals.

However, in 2016, this picture of a orange headed guy grabbing a pussy has a dirtier dimension. However, in this case, he really does mean cat. And no he shouldn't grab them by the scruff of their necks. Still pretty creepy.

However, in 2016, this picture of a orange headed guy grabbing a pussy has a dirtier dimension. However, in this case, he really does mean cat. And no, he shouldn’t grab them by the scruff of their necks. Still pretty creepy. So is the moon.

26. In this game, you can either bite into an apple or a flaming candle.

For the love of God, please bite into the apple. God only knows what kind of sick Halloween games people played during those days.

For the love of God, please bite into the apple. God only knows what kind of sick Halloween games people played during those days.

27. Folks, on Halloween, remember to keep a look out for pumpkin headed children who might steal from your yard, especially the gate.

Now stealing a neighbor's gate is one thing. But pumpkin headed kids doing it, well, that's just insane. Seriously, those kids are freaky.

Now stealing a neighbor’s gate is one thing. But pumpkin headed kids doing it, well, that’s just insane. Seriously, those kids are freaky.

28. Best wishes for Halloween now let’s watch a love scene with pumpkin people.

Yes, if I were the black cat, I'd wonder if I was totally tripping, too. For God's sake, acid had to play a role in this illustration.

Yes, if I were the black cat, I’d wonder if I was totally tripping, too. For God’s sake, acid had to play a role in this illustration.

29. “Instead of flying your broom, how about I drive you in my new gourd car?”

Even the witch is like, "I can't fucking believe this!" As if these pumpkin people are freaky enough. Now they're driving giant gourds.

Even the witch is like, “I can’t fucking believe this!” As if these pumpkin people are freaky enough. Now they’re driving giant gourds.

30. On Halloween, a giant jack-0-lantern makes a great make out spot.

Not sure what's freakier in this picture. Is it the couple making out while the jack-o-lantern doesn't seem to mind? Or the gourd people watching it?

Not sure what’s freakier in this picture. Is it the couple making out while the jack-o-lantern doesn’t seem to mind? Or the gourd people watching it?

31. On Halloween you might see a lot of strange things happening.

Oh, shit, it's the children's jack-o-lantern cult again. And it seems the tree and rock cliffs have come alive. There must be dark magic afoot.

Oh, shit, it’s the children’s jack-o-lantern cult again. And it seems the tree and rock cliffs have come alive. There must be dark magic afoot.

32. Halloween is always full of surprises.

And it seems the clown is freaked out by the pumpkin jack-in-a-box as I am. Hope he comes out alive but I doubt it.

And it seems the clown is freaked out by the pumpkin jack-in-a-box as I am. Hope he comes out alive but I doubt it.

33. Halloween is always a time of great fun.

And it seems the pumpkin head guy is looking at the woman's ass as she bobs for apples near the fireplace. What a perv.

And it seems the pumpkin head guy is looking at the woman’s ass as she bobs for apples near the fireplace. What a perv.

34. If green goblins cross your path, always have a jump rope in handy.

From I-Mockery: "It's Halloween! You know what that means! Yep! It's time to dress up like a clown and a witch and bust out the ol' jump rope!"

From I-Mockery: “It’s Halloween! You know what that means! Yep! It’s time to dress up like a clown and a witch and bust out the ol’ jump rope!”

35. There’s no better thing to do on Halloween than bob for apples.

From I-Mockery: "If you think the girl is up to anything but no good, you're a fool. Those are probably fake apples floating in a vat of acid that you're about to dip your face into."

From I-Mockery: “If you think the girl is up to anything but no good, you’re a fool. Those are probably fake apples floating in a vat of acid that you’re about to dip your face into.”

36. “Don’t pass an owl on Halloween/And good luck is yours if you haven’t been seen.”

From I-Mockery: "If 'good luck' equates to meeting twin pumpkinhead pieces of red corn on the cob witches, I think I'll take my chances with seeing the old owl instead.

From I-Mockery: “If ‘good luck’ equates to meeting twin pumpkinhead pieces of red corn on the cob witches, I think I’ll take my chances with seeing the old owl instead.”

37. Join in the Halloween jollity.

From I-Mockery: "Okay, two things here: 1) I just learned that "jollity" is a word. and 2) That pumpkin is totally going to murder that girl and make the owl watch the entire gruesome act.

From I-Mockery: “Okay, two things here: 1) I just learned that “jollity” is a word. and 2) That pumpkin is totally going to murder that girl and make the owl watch the entire gruesome act.”

38. On Halloween night, remember to hide your head while you sleep. You’ll never know where the goblins or fairies are lurking.

This is especially true if your Halloween candy consists of some very powerful hallucinogens. But these fairies aren't watching over to protect this woman from the goblins, which are also quite freaky.

This is especially true if your Halloween candy consists of some very powerful hallucinogens. But these fairies aren’t watching over to protect this woman from the goblins, which are also quite freaky.

39. Anthromorphized garden vegetables wish you a joyous Halloween.

From I-Mockery: "When making a card that reads "Joyous Hallowe'en" you might want to have your quality control department double check it to make sure everyone in the picture looks joyous." I think they all want to murder the gardener in his sleep.

From I-Mockery: “When making a card that reads “Joyous Hallowe’en” you might want to have your quality control department double check it to make sure everyone in the picture looks joyous.” I think they all want to murder the gardener in his sleep. But that’s just me.

40. Why should a witch fly a broom when she drive into the sky on a flying corn cob?

Of course, at least she's riding a sustainable vehicle. Still, seeing her flying into space on a winged ear of corn sounds more like an acid trip.

Of course, at least she’s riding a sustainable vehicle. Still, seeing her flying into space on a winged ear of corn sounds more like an acid trip.

41. Hail Halloween from the jack-o-lantern on the stump.

From I-Mockery: "HAIL! I'm pretty sure that pumpkin has braces. Perhaps it's a commentary on the dental work you'll need after overindulging on candy?"

From I-Mockery: “HAIL! I’m pretty sure that pumpkin has braces. Perhaps it’s a commentary
on the dental work you’ll need after overindulging on candy?”

42. Apparently, black cats freak out over jack-o-lanterns.

From I-Mockery: "While the cat looks frightened, the chestnut doesn't seem to be screaming. In fact, it looks quite pleased with how things worked out. My guess is that the chestnut planned this whole "scare the cat" prank. The lesson we all learned here? Chestnuts are dicks."

From I-Mockery: “While the cat looks frightened, the chestnut doesn’t seem to be screaming. In fact, it looks quite pleased
with how things worked out. My guess is that the chestnut planned this whole “scare the cat” prank.
The lesson we all learned here? Chestnuts are dicks.”

43. “We hoot a Halloween greeting to you.”

Pardon me for thinking this. But I sure as hell hope that the flustered owl rips that little pumpkin headed brat to shreds. He has it coming.

Pardon me for thinking this. But I sure as hell hope that the flustered owl rips that little pumpkin headed brat to shreds. He has it coming.

44. For witches, jack-o-lanterns make great reading lights.

"Now please let me read where it calls for eye of newt and tongue of dog. It's before preheat cauldron to 350 degrees, cook for 3 days under the full moon, and serves 6. And no, I'm not trying to turn people in to frogs this time."

“Now please let me read where it calls for eye of newt and tongue of dog. It’s before preheat cauldron to 350 degrees, cook for 3 days under the full moon, and serves 6. And no, I’m not trying to turn people in to frogs this time.”

45. On Halloween, it helps that you steal the gate of luck before the scary floating pumpkins go by.

From I-Mockery: "Well, now we know why they were stealing it... they were stealing the Gate of Luck! Of course! Why didn't I think of that! If there's one thing I like to do every Halloween, it's stealing gates from people's homes!"

From I-Mockery: “Well, now we know why they were stealing it… they were stealing the Gate of Luck! Of course! Why didn’t I think of that! If there’s one thing I like to do every Halloween, it’s stealing gates from people’s homes!”

46. Happy Halloween and please make an offer for the Pumpkin King.

Because if you don't, he'll sure as hell make you an offer you can't refuse. This is especially if he finds you attractive like this woman.

Because if you don’t, he’ll sure as hell make you an offer you can’t refuse. This is especially if he finds you attractive like this woman.

47. A witch sometimes enjoys traveling in a pumpkin boat once in awhile.

From Tracy's Toys: "Where has she come from, and why didn't she just fly, as would have been traditional? Where is she going, in her broom masted pumpkin boat? Is she a good witch or a bad witch? She's smiling, but I suppose that's not a sure thing: the witch in Hansel and Gretel was probably smiling warmly right up to the time she tried to cook and eat her little visitors. Is that cat safe? Why isn't he in the boat too? I'm worried he's going to fall off. And just how seaworthy is that pumpkin boat? Is there any danger of fish nibbling away the bottom? Won't water come through the face holes? Seems like a major design flaw there. This is definitely a postcard that raises lots of questions."

From Tracy’s Toys: “Where has she come from, and why didn’t she just fly, as would have been traditional? Where is she going, in her broom masted pumpkin boat? Is she a good witch or a bad witch? She’s smiling, but I suppose that’s not a sure thing: the witch in Hansel and Gretel was probably smiling warmly right up to the time she tried to cook and eat her little visitors…”

48. Demons always know when to feed more fire to a jack-o-lantern.

And it seems that the pumpkin is craving for more wood. Demons need to keep up the pace.

And it seems that the pumpkin is craving for more wood. Demons need to keep up the pace.

49. Hope you can use jack-o-lanterns to light up when on the town trick or treating or partying.

From I-Mockery: "If only I had a dime for every single time I've seen this same old scenario take place on Halloween..." Because aren't pumpkins a bit heavy to use as lamps. This must be based on an acid trip.

From I-Mockery: “If only I had a dime for every single time I’ve seen this same old scenario take place on Halloween…” Because aren’t pumpkins a bit heavy to use as lamps. This must be based on an acid trip.

50. There’s no Halloween frolic like dancing under a creepy pumpkin head.

After the dance is done, it's said that the pumpkin will choose one of the girls who'd later be escorted as a virgin sacrifice. She would never be seen again since.

After the dance is done, it’s said that the pumpkin will choose one of the girls who’d later be escorted as a virgin sacrifice. She would never be seen again since.

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