[neverending]

Classic
Frankenstein- Though Bride is my favorite horror film, I think without the first film as a pelude a lot would be lost, so I'd start with the original. Plenty of time later to get to the sequel.
Horror of Dracula- Bring on the other iconic monster with Hammer's masterful take on the tale, and introduce two iconic personalities, Cushing and Lee.

Gory
Well, my gory films won't actually be that gory. I'll reinterpret this category to mean films that up the ante with violence and scares.
Halloween- a near perfect masterpiece of terror.
Texas Chainsaw Massacre- Not that gory, but still violent and shocking.

Crazy
Repulsion- I'll go literal with this selection of a true masterpiece film depicting a woman's descent into madness.
Carrie- Original version. Some cheese factor, but Sissy Spacek and Piper Laurie elevate this film to brilliance.

Funny
Beetlejuice- It just doesn't get much funnier than this film while still managing some scares.
The Raven- My friend probably won't get why this film is so funny, but I don't care. I'll just be geeking out the whole time about Price, Karloff and Lorre.
I didn't choose Young Frankenstein because he needs to know more about horror before he sees that.

Nice post, Despare. It will be interesting seeing people's lists.