Can I use my Mac to play music stores on an old iPod shuffle? I want to plug my very old iPod shuffle it into my more current Mac and play from my shuffle's play list.  Can I do that and if so how?

I can see all the songs in "My Music" but cant play it.
This should be fairly easy. 


Simply select your iPod in the iTunes sidebar
Check the Manually manage music and videos box under "Options" (in the "Summary" screen).
Now you should be able to play your music from your iPod shuffle