When your work history has so many holes that...

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...it looks like it has the mange, how do you deal with it in a resume (especially if asked to supply a chronological resume)? A job interview (if the interviewer asks about it)?

I usually fudged dates to cover long periods of unemployment or short-term jobs that weren't worth mentioning anyway. Had a few interviewers actually call a reference or two, but I don't think anyone ever went to the trouble to check exact dates.

I don't know if this helps, but when I was learning about writing resumes, I remember hearing that if there is a large gap in your work history and there's no answer for it, they will assume that you were in jail.

If it's true that that's what they're concerned about, it ought to be OK to tell the truth: "I had trouble finding work" or "I needed to take some time off after school to decide on a direction to take" or something like that. Because that would allay any fears about you being in jail.

I think a better format is a "functional resume" if you have gaps.