I have about 1000 songs on mine at the moment. But I swear using the Random function the player picks from about the same 50 songs 80% of the time only about 20% of the time picks one from the other 950.

I mean as much as I like 10AM Automatic by The Black Keys I don't want to hear it 3 times on a 20 minute train journey. It's kinda pissing me off a bit.

I have the same problem. I swear my 20GB Ipod picks from "blocks" of my library and plays them for awhile and then moves on to another "block".

mine too. i reset my play count every coupla days and it seems to help considerably.

I've been around too many cd players that grab the skits/interlude tracks when put on random.

This is one reason I don't like foobar. It will pick the same song over and over on random.

I think there's an alternative plugin you can use for better random playback. I've never tried it though.

Get it here. 7th from the top.