No, it messes up ur ipod :(
Download itunes to your computer and then download a song from itunes store to itunes then hook up your ipod and your done
When you hook it up to iTunes for the first time
Simply hook your iPod up to iTunes, and select restore from the iPod menu.
You hook it up to a computer, go to itunes on internet, then buy apps.
You go to your iPod section on iTunes after you hook up your ipod, and check the box that says "automatically sync songs to iPod when hooked up"
on an ipod nano you just hook up itunes and it should pull up if your ipod is connected to the computer. if not go to "my computer" and it should be there and you can open it so it will work.
If it is saying you should hook it up to iTuens, it is not broken. You must, as it says, hook it up to iTunes, register your iPod, and download the latest software for it. Then, the iPod becomes useable. Your iPod is not broken, and this usually occurs if it is a new iPod.
delete the pictures off of itunes, then hook your ipod up to your computer and sync.
your iPod should have a connector that's plugs into your computer. Then when you hook up your iPod, something called Itunes, should come up. you can put a CD in your computer, and then if you have itunes open, the songs will go onto itunes. When your iPod is plugged in, itunes is up, and you have music on your itunes, something that says your iPod is in should be to the side. like if you use your name, it would come up as, "so and so's iPod" Click and drag songs to that, and then wait for your iPod to finish syncronizing. I hope i helped!!!
once you have purchesed some songs on iTunes, hook up your iPod to your computer. Then open up iTunes. when it recognizes your iPod, click it. (it should be on the lower left side of the screen.) then click the "snyc" button which should be on the lower right corner.
No you can't I have tried the only way you might be able is thrue a jailbroken iPod but again I don't know also might depend on generation