My 160gb iPod is contantly rebooting itself during playback

No problems at all while syncing. However, when I am using it, it plays 4-5 songs perfectly, then it randomly reboots from the Apple logo. Any ideas/suggestions?

You may not have a backup of those files, then.  Have you checked for backup according to this knowledge base article:
http://support.apple.com/kb/PH1779

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    Apple Retail Store - Genius Bar                                                              

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