So recently I've been ripping DVDs to my Zune in it's native 320x240 format. The problem is that ripping widescreen formats into 4:3 aspect ratio leaves those annoying black bars on top and bottom.

I'm not sure I understand your question but anamorphic material will always have to scale or stretch, there's no extra resolution there, it's the same number of pixels as a non anamorphic image by the ...