I tried playing from the file browser as well as from the database.
Here's something weird, when I hooked it up to a Vista machine, the rockbox folder game me a 'the folder or contents is corrupted' error message when I selected it. I tried the same thing on my normal Windows 7 machine and got no such error. I also scanned the file system in Vista and found some errors, so I guess something got corrupted but Windows 7 just didn't see it.
Reinstalling Rockbox fixed everything, I was just hoping there was an alternate solution. Thanks for the help!