1. Halloween/Halloween 2
I count these two films as basically part 1 and part 2 of the same film, due to Halloween 2 taking place literally right after the first film ends.
Psychotic mad man Michael Myers escapes from a high security mental home and makes his way to his home town of Haddonfield just in time for Halloween. There he starts stalking a shy young girl named Laurie Strode (Jaime Lee Curtis), killing off her friends until it's just her left. Meanwhile Dr Loomis; a man who was the Doctor in charge of Michael Myers rushes to the town, he knows that Myers is pure evil and must be stopped. This film was really effective in that you never really have a good look at Myers, he appears in shadows, stealthily taking out his victims, in the end credits his character is named just as 'The Shape'.
Halloween 2 is a much more gory, and action packed film. Having been temporarily disabled at the end of Halloween he now makes his way to the Hospital that Laurie Strode has been sent to. This film features more brutal killings, more nudity,and more action than the first, and has a satisfying end.
2. Murder Party
Another film set during Halloween. I have mentioned this film before on here. Basically a lonely geek finds an invitation to a Halloween party. He dresses up in a ridiculous cardboard robot suit and heads to the party, only to find out it was actually a elaborate trap set by a group of hipsters to kidnap someone and murder them as part of an art installation. Quite a funny film, though expect plenty of dialogue.
3. The Fear 2: Halloween Night
Another film I have wrote about. A young man invites his friends to his grandparents house for a Halloween party where the guests are supposed to dress as their biggest fears. Very silly, and badly made film with terrible effects, but fun in a so bad it's good kind of way.
4. The Nightmare before Christmas
The fantastic Tim Burton claymation film. The film is set in Halloween town where the Pumpkin King Jack Skeleton has become disillusioned with Halloween, and sets his sights on taking over Christmas with disastrous results. Though set in Halloween town, the film is much more of a Christmas film, but can be watched for both occasions I think.
5. Halloween 3: Season of the Witch
The odd one out in the Halloween series as it is a stand alone story. An evil toymaker (a Ken Dodd lookalike) plans to hypnotise Americas children to murder their parents via hypnotic messages sent out on Halloween. Damn annoying hypnotism sound, but is very Halloweeny, and if you can last the damn noise not a bad film.