The Ghost Goes West (1935)This British production is probably the least well-known entry in this list, but it's absolutely worth tracking down. It has a number of plot points in common with the later picture, The Canterville Ghost (1944), but in this story the haunted castle gets moved to the United States by a wealthy American businessman (Eugene Pallette), and the ghost (Robert Donat) is forced to come along. Donat plays a double role here as both the ghost and his modern day descendant, which is handy for leading lady Jean Parker. More romantic comedy than ghost story, this is such fun that it deserves to be seen by more people, which is why I include it here. It also features the marvelous Elsa Lanchester in a supporting role.
I Married a Witch (1942)
Veronica Lake stars as Jennifer, the witch in question in this hilarious screwball comedy with a supernatural twist, and Fredric March is the cursed descendant of the man who burned her and her father (Cecil Kellaway) at the stake many centuries ago. When their spirits awaken from a long slumber, Jennifer and her dad intend to resume their persecution of the stuffy, wealthy Wooley family, but love upsets the plans for revenge. Fun special effects, a wicked sense of humor, and a fantastic cast make this a perfect pick for the season.
Cary Grant might not have liked his work in this adaptation of the darkly hilarious stage play, but audiences loved him and it so much that it has been a perennial favorite for decades. Frank Capra directs a pitch perfect cast, many of them reprising their roles from the stage production, and Jean Adair and Josephine Hull run away with every scene as the dotty old aunts whose "charity work" involves poisoning elderly men. Although there's nothing supernatural about the characters, the story takes place on Halloween and costars horror regular Peter Lorre; Raymond Massey plays the murderous brother whose role in the original play had been filled by Boris Karloff, but Karloff wasn't able to to reprise the role in this film.
The Canterville Ghost (1944)
Loosely adapted from the story by Oscar Wilde, this is a ghostly comedy with lots of laughs and a surprisingly sweet heart, thanks to charming performances by Charles Laughton, Robert Young, and Margaret O'Brien. Laughton stars as the ghost, Sir Simon, who hopes to break the curse of his long, lonely existence by demonstrating the courage that eluded him in life. When a group of American soldiers are stationed at the Canterville family castle during World War II, Sir Simon meets Cully (Young), who might be able to help him. O'Brien's role as a central character and the themes of courage and friendship make this movie a great choice for younger viewers.
Abbott and Costello Meet Frankenstein (1948)
Universal was happy to transform its iconic monsters into comedy stars for this wonderful installment in the Abbott and Costello series of pictures, in which the duo play Chick (Bud Abbott) and Wilbur (Lou Costello), two hapless freight handlers who unwittingly get tangled up with Dracula (Bela Lugosi), the Wolf Man (Lon Chaney Jr.), and Frankenstein's monster (Glenn Strange). Hilarious antics ensue as the monsters scheme to remove Wilbur's brain and use it to restore Frankenstein's creature. Even if kids haven't seen the original Universal movies starring these characters, they'll recognize the monsters and get a kick out of this delightful film, but it's a must-see for classic horror fans of all ages.