For me, the easiest way to delete old songs from my iPod is to do it manually. To do this, I visit iTunes, and I choose the option that allows me to change songs manually. If you look closely on the left side of the screen, you will see the word "iPod" under Devices.
Click on the triangle next to the word, and iTunes will give you a list of the songs that you have on that iPod. Now, all you have to do is Delete that song. Scroll over the song until it is highlighted.
Now go to the Edit menu and hit delete. That's it!
There are two ways of it. 1) connect your ipod to your PC through USB cable and go to that removable disk drive and open it. There you will see the list of your songs go to that file and press "Delete" from keyboard.2) Connect your ipod to itunes then highlight the songs by checking the box which you want to delete and press "delete" from keyboard.
Then just drag the playlist over.
Sync your iPod with iTunes. Then remove the song from the playlist in iTunes. Then sync again.
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