Songs on iPhone playlist completely different from playlist in iTunes

I have a smart playlist "Most Played." It's pretty simple: Limited to 50 items selected by most often played. Works fine in iTunes, however the playlist on my phone contains 50 completely different songs in no order that I can make any sense of. In fact, they seem to be songs that I rarely listen to. I've tried altering the playlist, and even deleting the playlist and recreating it, but it still picks the same obscure 50 songs. Why would a playlist on the iPhone be different from the same playlist on iTunes?

I have the exact same problem. My "Most often Played" playlist which appears fine in iTunes and fine when viewing the list in iTunes (but on my iPhone) when I disconnect from the computer this playlist is full of songs I have listened to a couple of times and basically don't care for. I've tried renaming the playlist thinking it had something to do with the 'M.O.P.' naming scheme. I've deleted the entire contents of the playlist and re-synced, but nothing seems to change these weird songs from appearing in my most often played list. I noticed this after the 3.1 update, but can't be completely sure when it started. This is annoying. My plain old iPod maintains the library much better than the iPhone iPod. Any suggestions? Seems like every time we want the iPhone to act like an iPod, we have to do a bunch of tricks to get it to sort of work. Personally I blame it on windows compatibility, the more compatible Apple makes their stuff with windows, the less reliable and kludgy their stuff gets. (Sorry didn't mean to blame Windows, just frustrated.)

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Songs on iPhone playlist completely different from playlist in iTunes

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