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Gaps of more than six months -- Be creative if you can, like list jobs from Fall 2001-Spring 2002, or just from 2001-2002, if you think you can get away from it. Explain in the cover letter or interview what you were doing with that time if you think they will be suspicious (In interviews, I said, "I didn't want to rush into anything until I was sure it was what I wanted to be doing, and now I KNOW this is truly what I want").
If your experience doesn't line up, that is usually fine. It's what you as a person have to offer... Tell your life experiences and how they prepare you for things... You can make anything relate because whether you have been in law, fast food, retail, whatever, you still have to deal with similar concepts -- ethical decisions, high-stress situations, working with people with different personalities than your own, etc...
It's not how far you go back listing education/experience... it's why. Think about each thing you put on your resume and how you can use it to support why you are the bst person... list what you feel is relevant. (Only exception to this... don't list high school stuff unless you have a DAMN good reason)
GET IT ALL ON ONE PAGE!!! Can not stress this enough... You're experience does not require more than one page unless you are much older than you are. Learn the art of brevity...
GOOD LUCK!
(P.S. I swear I am not making this stuff up... I am a job-hunting/interview queen and these have all worked for me)
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