Jesse-
My dad has some program called Snag-It32, it allows multiple images on a clipboard at once. I'm not sure exactly how it works, cause I rarely used it. I can check next time I talk to him. I think it is freeware or at least share-ware. anything else will run you some $$$.
If you are ripping screens from DVDs you will need to turn hardware acceleeration off (or down.) To do this right-click on the destop, click properties, then in the properties window click the Settings tab, then click the advanced button, next you are going to want to click the troubleshooting tab and there should be a bar that lets you dial down the hardware acceleration. Turn it down as far as you need to to be able to get screenshots, which most of the time is off. This should get rid of any "wonkyness" and won't take a shot of just a black screen sice DVDs play on a different layer then the rest of the stuff you see on your monitor. Hardware acceleration compresses it all into one layer so that it is all visible and the print screen key will actually get what you see on screen.