If I have two W2's and one is less than $500, do I have to file it on my taxes?

yes. All income has to be reported. If you earned more than $6300 then you are required to file a tax return. All income from all sources has to be reported.
If you earned less than $6300 for the year, then a return is not required. However, if any taxes were withheld from that income, then you "should" file a tax return anyway, to get those withheld taxes refunded to you.

Yes, you do. You must claim all W-2s that you get.