You can compress your files into 32kbps mp3 files and fit most of them within 8 gigs. Might be a wise idea since iPod audio quality is shit anyway, even at a lossless format. Videos, forget it.
I know it seems like I hate Apple, but I don't. I hate their products. But I love them as a corporate marketing conglomerate and their target audience of average, naiive consumers who know little to nothing about digital media and sound. In fact, I bought $2K worth of Apple shares since I heard about the iPhone last week and there shares went up 7 dollars, making me a few hundred.