Can't listen to Podcasts from 2007

I have a number of podcasts I've recently subscribed to, and I've downloaded earlier shows/videos from before January 2008. However, I can't transfer any of these to my iTouch. I select them, drag them to the iTouch, and nothing happens.
It's running the 2.0.2 software, and it never used to do this. It may have started after I upgraded it.

Hi zoarpirate,
If you are having an issue with your iPhone not playing podcast and other non-phone call sound through your Bluetooth headphones, and have already tried resetting without any change, I would suggest the next step is to back up any data on your iPhone and set it up as a new device. See this article for how to do so -
How to erase your iOS device and then set it up as a new device or restore it from backups
Thanks for using Apple Support Communities.
Best,
Brett L 

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