Why do some playlists not work in shuffle mode?

New iphone 5, same music as on my old iphone 4. When I select shuffle a playlist, it flips through about 3 songs and returns to list page, doesn't play any.. Sometimes plays last song in list and then returns to list page. Is there a setting I'm overlooking? This is my fourth iPhone and have not had this problem ever.

- Try cleaning out/blowing out the headphone jack. Try inserting/removing the plug a dozen times or so.
- Otherwise their either a problem with the headphone or the jack in the iPod

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