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Vague Rant:
Is naming files using track numbers really a "hack" in any legitimate sense? It seems like fairly standard behaviour to have filenames as %track% - %title% (and sometimes %artist% in there somewhere for VA albums). It's kind of just the default case for anyone who wants their music ordered by track.

Something that might have you confused about your track ordering is the behaviour of some (I'd say inferior) DAPs which implement no sorting and read directly from the FAT (the index of your files). If you've reordered them in another application before copying them across, then barring Windows's sometimes awkward function (copying over the last file then starting from the first and working to the second-from-last is something XP loves to do), the files would be entered into the FAT in the order you see represented in Explorer.

Basically, on players that do this, the tracks are displayed in the browser in the order you copied them across, meaning there's no reason why "09 - Meet Me in the Basement.mp3" couldn't come before "01 - World Sick.mp3", and further, no reason your "XTC" directory couldn't come before "Dexys Midnight Runners"; it just depends what you copied first. With this behaviour you could have tracks "sorted" by a sane order without naming them anything meaningfully sortable, but it's a horrible burden to have to keep everything in order (although there are tools which do alphabetical sorting of the FAT itself, however these would once again ruin your track ordering) as any time you want to add something you need to remove everything else just to make sure it all goes back in the right place.

EDIT: In short, the only way to have tracks sorted by track number in an alphabetical (alphanumeric technically) sorting system is to have the track number in the filename. If you don't want track numbers in your filenames, the database is your only real option.

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