As far as I know, in the United States you can pay in any denomination for any goods purchased. That being said, any business can develop their own policies to prohibit certain types of payment (i.e. $100 bills at gas stations where they only keep $20 worth of change in the register). I have heard stories of people trying to pay with several thousand pennies, and get cited for disorderly conduct. Some states may also have their own laws governing legal tender.
All that aside, the laws are different in Canada. Although we no longer use the penny, the most pennies you can use in a single transaction is $0.25. You can spend up to $5.00 with nickles, $10.00 with dimes, quarters, and fifty-cent coins, $25.00 with loonies ($1 coins), and $40.00 with toonies ($2 coins) or $5 bills. Alas, not a lot of people are familiar with the Currency Act and it's not strictly enforced.