re:
I think depends on the job you are trying to get and the job(s) you've had. For example, I've been at the same place for 16 years and had a multitude of positions there. If I were to look for another job, I wouldn't go chronologically because that would only be one entry. I'd instead focus on the positions I held and how they related to the job I want. For example instead of year by year, I'd list position 1, position 2, etc.
One other word of advice, in many companies a human doesn't even read your resume at all. It's scanned through a software program that is looking for key words. If you know what kind of job you're looking for, it pays to know what key resume words are associated with it.
I'd highly recommend looking at sights such as monster.com and salary.com for some resume advice.
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