Jesse,
How many pages are you talking about? Your playbill should be 5 1/2 by 8 1/2 inches, or a regular letter sized sheet folded in half, and there will be four pages on each sheet of 8 1/2 by 11 paper. Therefore, the total pages on your playbill should be a multiple of four. 4, 8, 12, 16, etc. If you need fewer pages than one of these round numbers, you're going to have to leave some pages blank. Maximum blank pages will be 3. Anyway, take a number of blank sheets of paper, stack them and fold them in the middle. Now staple them, right in the fold. (The fold is called a gutter.) That's your booklet mock up. Turn it the right way and look at it as you would look at a finished playbill. Write the page number on each page. Dismantle your booklet. Look at each sheet. It marked with page numbers according to the way they should be oriented and printed in order to appear correctly when bound. Now set up your page on Word to print in landscape and make two columns. Each column will be one page of the playbill. If you had a four-page playbill, one page on your computer would be -- from left to right -- playbill pages 2 and 3, and the opposite side would be playbill pages 4 and 1. (Not 1 and 4!) I hope this makes sense.

If you absolutely can't get your program to produce the pages 2-up (2 program pages on one letter-sized sheet) in the proper order, or the instructions you've gotten here are confusing, set up a letter-sized sheet in landscape and create two columns on it. The columns will each be one playbill page. Type up your pages in the order that you'd like to read them in, print them out, and cut them in half so you have individual 5.5"x8.5" program pages rather than 2 pages on a sheet. Then either glue them down on a letter-sized piece of carboard in the order that NicH suggested, or take the pages to your local quick printer, show them what you want to do, and ask them to show you how to lay it out. You can ask their advice even if you plan to eventually photocopy the program yourself -- they get questions like this all the time and are usually happy to help you. Get an estimate on the cost to let the printer do it instead while you're in there, and you may find that it's cheaper to let them do it.

I agree with using Word Perfect - it is far better than MS word - easier to format a document the way you want rather than the way the program wants to format it. I have been able to make the pages come out easily in WP.