If you are updating automatically (syncing) all songs and playlists then delete the files from the iTunes library. In the iTunes Library highlight the file and press the delete key on your keyboard. If you're updating the iPod from a selected playlist delete the song from the playlist and it will remain in the library. Next time you connect they will deleted automatically from your iPod.

If you are updating manually, connect your iPod and when it shows in the iTunes source list click on the chevron (the little triangle) to the left of the iPod icon This will display the various icons for the iPod itself, Music, Movies, TV Shows and Playlists. Click on Music and you'll see the usual song list. Find the files on your iPod that you want to remove, highlight them and delete directly as above by pressing the delete key on your keyboard.

To select multiple items such as all the songs in an album, click on the first track in the list hold down the shift key and click on the last track to highlight the selection. Then press the delete key.

Answered by Deepak , an ibibo Advisor, at 12:59 AM on December 13, 2008

Connect your iPod to your computer, wait for iTunes to come up, select the "Music" section under your iPod on the left hand side, right-click any of the songs you don't want and delete them. They'll be deleted from your iPod but will remain in your iTunes library until you delete them from that as well.

Answered by ayisha , an ibibo Master, at 12:51 AM on December 13, 2008

If you prefer to manage the songs and playlists on your iPod separately from the way you manage them in iTunes, start by setting iTunes to Manually manage the content on your iPod.

Next, Click the gray triangle icon next to your iPod in the iTunes Source pane. This will allow you to see the contents of your iPod. You can add playlists and songs store in iTunes to your iPod simply dragging them to the iPod in the Source pane.

You can remove items from the iPod by highlighting them as they appear on the iPod and choose Delete from the Edit menu.

Answered by Suparna , an ibibo Master, at 12:15 AM on December 13, 2008