I would suggest that the best place to start is “Shadow Over Innsmouth.”
It’s a very well-constructed story with a great twisty ending. It’s got the “family curse” plotline that you often see satirized when cartoonists go after Lovecraft! I just love this story. So much fun.
Another good story is “The Colour Out of Space.” This is a wonderful, touching story that anticipates nuclear fallout, radiation poisoning, etc… From what I’ve read, H.P. Lovecraft was an avid reader of scientific journals, and it shows in this story. Very good character development, too. IMO, this story seems like it really happened, and I wonder somtimes if he’s really writing about a family that was excluded due to madness, sexual sin, or something else that caused their small town to reject them. OR…maybe he was writing about himself and his unusual and lonely family situation.
A third good story is “Imprisoned with the Pharoahs,” which was ghost-written by Lovecraft for Harry Houdini!
“In the Vault” is not part of the Cthulhu Mythos. It’s just a fun horror/ghost story. There’s actually an urban myth that is very simliar to this story. I wonder if the myth existed back in the early 20th Century, and if Lovecraft turned it into this story.
I agree about “The Outsider,” although IMO, this story reads more like Poe than Lovecraft. IMO, it doesn’t have the usual “fun” in it that many of Lovecraft’s other stories have. “The Outsider” is truly sad. Again, I wonder if Lovecraft was writing about himself. Is HE the “outsider” in this story? I think so.
For the poster who asked, “Cthulhu” is just a word. It has no association with Satan. “Cthulhu” is the “head god” of the Old Ones. H.P. Lovecraft created a milieu in which the Old Ones (the bad guys!) were defeated eons ago by the Deep Ones (the good guys!), but Old Ones still lurk under the water or underground (especially in basements, cellars, tombs, catacombs, and any other underground areas!) waiting to return and destroy the earth. (Bwoo ha ha!)
Most of the Cthulhu Mythos stories are about forays by various Old Ones back into Earth, mainly when evil misguided humans invite them back. The Old Ones and the evil humans are thwarted or defeated by good humans who often call upon the Deep Ones to help them. A lot of the stories have “near misses”–e.g., in “The Dunwich Horror”, Professor Armitage barely makes it to Dunwich on time to say the spells to stop Wilbur Whateley’s awful twin from eating up everyone in town!
Do these stories sound kind of “fun?” YES! They are fun!!! You cannot take H.P. Lovecraft stories too seriously! You cannot look for a devil in every story, because you won’t find one. Instead, you’ll find a young man who was invalid, lived with his two maiden aunts in New England, and wrote to expand his very small world and make it more exciting. In other words, he let his imagination run wild and free, and had a good time creating wonderful scary creatures and brave heros who overcame these creatures.
H.P. Lovecraft wrote with a twinkle in his eye. He was not trying to spread Satanism, he was just creating a really well-organized “boogey-man world” for kids and grown-up kids like me. His stories make you shiver, but it’s a “fun” shiver, the kind ot thing you do when you see kids dressed in Halloween costumes coming up your sidewalk.
Lovecraft’s use of exaggerated descriptive language makes them somewhat humorous; you find yourself reading wide-eyed, and then you sit up and say, 'Oh, come on now!" Only in Lovecraft stories do you see words like “lugubrious,” “gibbous,” and “ululations.” Great words!
Lovecraft corresponded with several young teenagers who became famous writers, including a teenaged Robert Bloch (author of Psycho). He was kind and encouraging to these young people.