a question of synchronizing ipod classic

I made a playlist of my library.  It shows that I have 77 songs on my computer.  after syncing with my ipod, the ipod said I have 76 songs in the playlist.  the song I'm missing is roy orbison pretty woman.   not a big deal I know but I tried to synchronize twice.  I even added a new song to the playlist, and when I synced again he picked up this song, but still shows no pretty woman.  What have I done wrong?  any ideas how to add this song to my playlist of the ipod?  Thanks in advance

I know that apple company supports more portable ipod... < = so sad... so that I posted in the "Accessories" category, hoping someone can help... maybe not?

Tags: iPod

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