This retelling of "The Monkey's Paw," W.W. Jacob's 1902 short story, aired in Canada in 1991 on Halloween night and was directed by D.J. MacHale, the Orson Welles of AYAOTD. Two friends, Dougie and Kevin, decide to grow some balls and go trick or treating at Miss Clove's house, the neighborhood witch. After scaring the shit out of her, they return to apologize and she gives them a magical claw which grants the owner three wishes...with consequences. So what would two tweenagers filled with piss and vinegar wish for? Well, Kevin blows a wish to win a track medal, Dougie unintentionally kills his parents and then raises his grandfather from the dead. Super creepy vibe throughout the entire episode and Miss Clove's laugh still haunts my dreams.
4) The Tale of Old Man Corcoran
Brothers Jack and Kenny are two inner city kids (black) who move to the boring side of town and have a hard time fitting in. They're approached by a gang of neighborhood hoodlums who invite them to play a nighttime game of hide and seek in a graveyard. That would've been my first hint that there's something off about these kids. But Jack and Kenny go anyway and before the game starts, a raging lesbian named Cissy Vernon tries to spook them off by telling them the story of Old Man Corcoran, the grave digger who wields an axe and plays mouth harp. The scenes in the graveyard are eerie, sure, but it's the twist at the end that makes this episode super creepo and memorable.
3) The Tale of the Nightly Neighbors
Emma and her smartass brother Dayday are paranoid that their new neighbors, the Brauns, might be vampires. While they may just have over-active imaginations, you can't really blame them. The Brauns are from the Ukraine, only come out at night, and keep refrigerators of blood in their basement. Anyone in their right mind would bust out the crucifixes and garlic necklaces. The first and greatest of all the AYAOTD vampire stories, season 1's "Nightly Neighbors" features one the series' best endings. It also happens to be an ambiguous ending, something rare for a series flooded with happy ones.
2) The Tale of the Dead Man's Float
This is the first tale told by Stig, the Pig-Pen of the Midnight Society. This racy tale of teen romance features a chemistry nerd named Zeke who would do anything to get closer to swim team superstar Clorice, who obviously wants nothing to do with him. But Zeke wins her over by showing her an abandoned swimming pool he found while trying to "calculate the volume of the school." Don't laugh, Zeke probably hasn't discovered masturbation yet. But this pool was hidden away for a reason...a bone-chilling reason! It was built over an old graveyard, but one of the bodies was left behind and now their spirit enacts revenge on all those who dare go for a dip. The episode plays on the fear of drowning and hosts a gnarly looking spirit. To a degree, it also plays on Zeke's fear of taking his shirt off when he goes swimming, which many of us can probably say from experience, does not hide shameful physiques at all.
1) The Tale of Laughing in the Dark
"Pick the right door and free you'll be. Pick the wrong door and there he'll be."
This season 1 episode is cited by many as the scariest episode of all time and it's easy to see why -- it's got a fucking clown in it. The clown in this case, Zeebo, worked in a carnival during the Great Depression. Desperate for money (like every other schlub during this time), Zeebo stole the park's payroll and hid out in the spookhouse. But Zeebo was careless with one of his cigars and the spookhouse caught fire; burning Zeebo to death. As a memorial to the thieving bastard, the carnival rebuilt the spookhouse and put a dummy of Zeebo inside, dooming the place to be haunted. Years later, Josh (Christian Tessier, who would go on to play Lt. Tucker 'Duck' Clellan on Battlestar Galactica) decides to prove how tough he is by stealing the red nose off the Zeebo dummy. Urban legend turns into reality as Josh is visited by the ghost of Zeebo. Everything works out in the end (seriously, where the hell does a 12-year-old purchase a box of cigars?) but not before some seriously scary shit goes down. Everyone remembers the laugh, the balloon, the phone call, and all the other nightmare-inducing tricks that drove many to check our closets before bed. It's like the writer of this episode was pissed at his kids and decided to scar them and the rest of us for life.