Songs In My "Most-Played" Playlist That Shouldn't Be

Okay, this is a weird one to try to explain, so please bear with me. On my iPod classic, I have a smart playlist I created called "Top 2000 Most Played Songs," which is, obviously, a playlist of the top 2000 most played songs on my iPod. Being a smart playlist, it always updates as play-counts change. When I look at this playlist in iTunes, it is all perfect and has all the right songs. When I look at this playlist on my iPod, it has about five or six songs at the bottom of the list that should not be there... i.e., they are songs that used to be in the top 2000 most played, but have since been pushed out by other songs. However, the playlist clearly only has 2000 songs on it, so there are five or six songs missing that are supposed to be there. However, the songs that are missing are not the most recent additions, because I have been able to find them in the playlist. So I don't know what is missing. I have tried copying to play order, and it still has those five or six songs at the end of the playlist. I don't want those songs on the playlist. Why is it doing this?

The most likely thing is that your songs that you expect to appear in the bottom of the list, still don't have more play-counts than others.
What you are trying to say is that iTunes does not updates your playlist. So try the experiment. Activate "Plays" column in iTunes. Connect ipod, let it syncronize. Look at the bottom of the list, see what is there. How many counts for the songs you expect in the list? More than for the others? Less or equal? As I see in my library, the songs in the bottom have the same play-counts, some of them will be in the list, some not (alphabetically?)
Then disconnect ipod and check the playlist on the device.
Also you can add new conditions to your smartlist to filter bad songs.

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