The iPod is primarily designed as a device whose content is loaded onto it in a one-way direction from iTunes, where you do all your music organization. You make all your changes in iTunes and then sync them to the iPod, where you don't do much but passively enjoy the music. Aside from setting star ratings and having the iPod report Last Played dates back to iTunes, there doesn't seem to be much you can do with the iPod that's then reflected back into iTunes the way iTunes' information is loaded onto the iPod.
Navigate to Music on the iPod
As described in Find and Play Music on the iPod, navigate through the music on your iPod using the various subcategories of the Music menu. Drill down through Artists, Albums, Genres, Songs, or other options to reach the music you want to organize into a playlist.
Add Songs to the On-The-Go Playlist
Use the wheel to scroll to each appropriate item you want to add to a newly created playlist. This can be a single song, a whole album, an entire artist's work, or any other listed item in any of the navigation listings. Place the highlight over the item using the wheel, and then press and hold the Select button. After about a second, the highlight blinks a few times; this means that the item has been added to a new On-The-Go playlist. Repeat this process by navigating to further songs or other items; hold down the Select button to add each one to the new playlist. The songs appear in the playlist in the sequence that you add them.
Note
You can create new playlists using the On-The-Go mechanism, but you can't sort them manually or rename them. To do this, you must synchronize the iPod with your computer and then edit the playlists in iTunes. See Step 6.
You cannot add videos to an On-The-Go playlist.
View or Play the On-The-Go Playlist
At any time, you can go back to view the songs you've added to the On-The-Go playlist. To do this, first return to the Main Menu. (Press Menu several times until iPod appears at the top of the screen.) Then choose Music and then Playlists. Scroll to the bottom of the Playlists screen. The option at the bottom is On-The-Go. Highlight this option and press Select.
All the songs that you added in Steps 1 and 2 are listed in order on this screen. If you added groups of songs, such as entire albums, the songs in those groups are added in the order they're listed in the iPod's navigation lists.
Press Play/Pause to play the contents of the On-The-Go playlist as it stands.
Save the New Playlist
If you want to close off an On-The-Go playlist that you've been building and begin creating a new one from scratch, you can do so by saving the first playlist. Scroll to the bottom of the On-The-Go playlist screen. Two options are available: Clear Playlist and Save Playlist. Choose Save Playlist and press Select. On the next screen, you can either choose Save Playlist or Cancel; choose Save Playlist.
The On-The-Go playlist is saved as a new playlist with the name New Playlist 1. The new playlist appears right above the original On-The-Go playlist in the Playlists screen. The original On-The-Go playlist's contents are cleared.
You can now go back to your music and add more songs to the original On-The-Go playlist. If you save this new playlist, its name becomes New Playlist 2, and so on.
Clear the Playlist
To clear the contents of the current On-The-Go playlist without saving it, choose Clear Playlist from the On-The-Go playlist screen. Choose Clear Playlist in the confirmation screen. The accumulated songs are removed from the list, and you can start over from scratch.
Synchronize Your iPod with iTunes
When you connect your iPod to your computer using the Dock or cabletransferring newly added music to it and downloading the changes you've made while on the goyou'll notice that one or more new playlists have been added to the Source pane in the iTunes window: On-The-Go 1, On-The-Go 2, and so on. The numbers in these playlists correspond to the numbers of the On-The-Go playlists that you created on the iPod; for instance, New Playlist 1 on the iPod becomes On-The-Go 1 in iTunes. Even if you did not save the current On-The-Go playlist on the iPod, its contents are copied into a new playlist in iTunes with a number reflecting what number it would have been given if you had saved it.
During the sync process, the newly renamed On-The-Go # playlists are copied back to the iPod, the iPod's New Playlist # entries are removed, and the active On-The-Go playlist is cleared.
You can now rename the On-The-Go # playlists within iTunes, rearrange the songs in them, and delete the ones you don't want. (See Create a Playlist for more.) The next time you sync your iPod, the changes are transferred back to it to match the newly edited playlists in iTunes.