This list was harder than I thought. I honestly thought it would be easy to scrape up a handful of funny horror movies, or scary comedies, or even unintentionally funny, Ed Wood-type movies. But the more I started poking around, the more I discovered a healthy and thriving subgenre, packed with potential classics. This year's hilarious, disturbing Black Sheep is just one example, as well as Fido (which I missed). There were also many shades within this subgenre, ranging from flat-out comedies with supernatural elements (Beetlejuice, The Witches of Eastwick) to horror movies with just a hint of the absurd (The Invisible Man, An American Werewolf in London) to spoofs (Young Frankenstein, Scary Movie) So I stuck with my original impulse and went with the ones that I found the "funniest" that were actual "horror" movies. Oddly enough, most of my choices went -- arbitrarily -- to zombies. I guess vampires and ghosts just aren't as funny.
1. Shaun of the Dead (2004)
I've seen this four or five times now, and I just don't get sick of it. On a purely technical level, it moves beautifully, from the camera setups and tracking shots to the fluid editing. It's so well executed that the jokes are more or less imbedded within the film, rather than jumping out of the film, so that it remains funny each time. Some of the subtler jokes get better each time, such as Ed's "two seconds." What's even more amazing is how well it works as both a character-driven movie and a zombie movie. It's so good, it even earned the seal of approval from the zombie master, George A. Romero (the boys, Simon Pegg and Nick Frost, went on to make cameos in Romero's Land of the Dead).
2. Army of Darkness (1992)
The debate rages on around Sam Raimi's Evil Dead trilogy: which one is best? I love them all, and Evil Dead II is my admitted favorite, but this third entry -- at one time entitled "Medieval Dead" -- is definitely the funniest. Bruce Campbell earned himself a lifelong cult following with his deadpan readings of lines like "boom stick," "primitive screwheads," "gimme some sugar, baby," etc. The drawback is that this film is definitely the least scary of the three films, but it does have its share of monsters, gore and creepy Harryhausen-like effects.