160GB Classic doesnt seem to update playcount in iTunes

There seems to be a bug with playcount updates, so you're not alone. Perhaps it can be fixed with another update someday. One possible contributor to this might be purchased games on the iPod. If you have played many songs since your last sync (>50) and then play one of the purchased games you may wipe out the recent play history since your last sync. I can't say for sure that's what's happening to you, but this does happen on my 5th generation iPod and it sounds exactly like what's happening with the Classics. Perhaps the Classics have other memory-hungry utilities (e.g. Coverflow) that wipe out the recent play history, just like games seem to. For me the workaround is to sync more often, or just avoid games.

did you make sure the song was played ALL the way through or skipped 9 seconds before the song ended ??
yes, I am sure that the songs played 100%. These songs play when the kids are in the car - many of them play at least once per car-trip, some of them play multiple times. There is no reason that the maximum number of plays should be 4 - many of them have played so many times, I can hardly stand it :) .
One possible contributor to this might be purchased games on the iPod
I did purchase the Soduko game - but I thought that update 1.0.2 fixed the playlist issue...

Please, please, plase help me out!!! I'd like to make a smartlist that play songs that haven't been played to play first. However, the way it is working now, the same songs play over and over and over again no matter how many times you play them (while other songs do not play at all...)

I have a plain ol' 5th generation video. Maybe Apple fixed it for the 5.5G, then broke it again for the Classic (wouldn't be the first time).
I'm not exactly sure what you are trying to add as I was specifically asking about the 160GB (or current 6G iPods) models.

I'm not exactly sure what you are trying to add as I was specifically asking about the 160GB (or current 6G iPods) models.

Sorry that you are offended that I brought up the 5th gen he was replying to me not you.

Anyway as said this is a known issue with the Classic, according to some the 1.0.2 update fixes this issue but I do not know as I no longer own the classic. Eitherway you'll probably just have to wait for a new firmware update or don't play games.

It happens on the 80 GB too, I'm afraid. It's such a pity, because Music Quiz is a blast! I hope they deal with it soon.