anyone know of a utility that would allow you to randomly select files from one directory and move them to a target directory until you hit a filesize limit of X MB (650MB or 700MB, in case you couldn't guess)? Wish I had some C skills, probably a very simple program.

Hmm.. considered looking at the status bar of an Explorer window? It shows how much data there is in each folder. You could leave it open as a second window, drag'n'drop files on it, and always see how much space they need altogether.

well, as it stands right now, my main 'playlist' directory contains 1,781 songs, 9.4GB of data, and what I was hoping I could do was just randomly create some CDs whenever I felt like it by randomly trolling that dir for 650 or 750MB of data. The point being random, I don't want to go through it myself and pick out this song and that song, there's just too many.

whoops, 650 or 700 that should've read

Howbout this, browse to your playlist folder in Explorer then sort the music by maybe Filesize or Type which should mix them up then Select enough of them until you see ~700MBs in Explorer's status bar and drop them into another folder. Should only take about a minute or so.

that's an idea, but for me it wouldn't do the trick, as I would be looking to make ~10 *random* CDs, and doing so relatively often, not just one group, one time, that happens to be 650/700MB

Maybe this little tool can help you: Burn To The Brim. It was made to not waste space when backing up files. Perhaps it can be missused for your purpose. If you run linux, you might easily get away with a perl script. Mix that with a mysql database of all your files and you can allways have different files on each of your cds. Usefull for random backup over a longer period of time.

interesting, thanks Gecko, I'll give that a whirl and see how it goes. I see in the overview that it tries to use up the biggest files first, so I am not sure how well it will fit this specific job in the long run, but it looks like it'll help in other scenarios anyway. I vaguely remember a program similar to this for filling up floppies, haha

waddya know, there it is
FILL.ZIP Size: 32074 Date: 1988-08-07 Time: 01:38:40
Use this program to fill up floppies to their capacity.

well, I don't know why I didn't think of this before, but this will do the trick just as well I suppose. I found a mass renamer that will randomize filenames, and that'll accomplish the goal, if not as elegantly as I'd hoped, but accomplish it just the same.

http://www.automation-software.co.uk/prod_mr.htm