Some random songs/albums won't play on iPhone

I bought an album off of iTunes but after I synced my iPhone to my mac, the songs won't play on the iPhone. I did a spotlight search on the phone and it says they are on there but they won't play. I have my phone hooked up to my computer right now and it says i should have 1818 songs on the phone but in the phone's about section it says I only have 1773 songs. The unplayable songs range from being imported cd files to purchased songs from iTunes. I've tried restoring my phone, performing some disk utility stuff, reimporting my library on my mac, a lot of restarting and what not. Can anyone help me out here? Thanks!

I've had the exact same problem, and I think it's related to the iOS 4.2.1 update. Certain songs will simply not play on my iPhone after the 4.2.1 OS update, even though they work fine in iTunes. I've re-synced multiple times to no avail. The problem also happens with ringtones, which means I've missed a number of alarms because the ringtone I chose for the alarm no longer works on the iPhone!
I really hope Apple is planning to release a fix for this. It is incredibly frustrating.

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