What JavaScript regex do I need to distinguish between a comment and a file path?

I need a regex. It need not be complex but must cover all bases. Requirements follow:

The file pattern I am forced to follow is such that a file looks like this:

chest/.setup.js
chest/**/*-chest.js
--choppers something:hello-there/wasup
--respite  spoc
--chow ./chest//test.bootstrap#1
--chow ./chest/server.bootstrap#
--blow 200

I must support thousands of other files that have a similar look.

I want to support comments in these files using just one of // or #.

My code needs to rip out the comments from the file contents before processing using regex matching.

I haven’t decided which comment syntax to use yet (please no answers that lump both together since only one will be used).

A comment may be at the start of a line (commenting out the whole line) or on the same line at the end (commenting out everything after it).

File paths may be “naive” and contain double slashes like so … /path//to/file/example.js

Also remember that # is a valid filename character and filenames can contain spaces on some operating systems.

My questions are:

(1) What regex is needed to rip out comments if I use the // syntax?

(2) What regex is needed to rip out comments if I use the # syntax?

Please feel free to answer (1) or (2) or both individually but not together.

If there are any other considerations that you feel I should take into account, please advise. Answers preferred in ES5 syntax (an annoying restriction).

What JavaScript regex do I need to distinguish between a comment and a file path?