I don't suppose any of you are lawyers?

Basically I'm writing a movie about a guy who starts wearing a Mike Myers (Halloween) mask as a way to cope with the outside world. What would I have to do to make this legal? The characters refers to himself as Mike Myers and everything.

Also, later in the movie he would meet a guy who dresses as Spider-Man. Same question: How do I make that legal to use in the film?

And yes, it's a comedy. Though I think a drama with that premise would be equally as amusing
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Give Mike a call. Not to mention Stan.
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Alter the names a bit? Mikey Myers and Spiderdude? lol spiderdude sounds retarded but it's just a suggestion. And you could change the mask a bit? idk

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Yeah...you can't do that without getting written permission from the owners of the characters.

Which you won't get.

Better re-write your script.
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As long as you are making this for your own personal amusement and not to make money in any way I don't think they would really care.
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well if you write the script and they want to make it into a full fledged movie or play than the movie company or w/e would prob take care of that (especially if its the same that made halloween), if its not going to be anything major and your not making money from it (or very little) than they probuly wont care