My ipod won't play songs I bought from itunes, and it won't let me download new ones.

How Do I Download Songs Onto My iPod Nano?
IPod Nanos are portable multimedia players that allow you to playback songs and other content (e.g. video) no matter where you go. They come in a variety of memory sizes such as 4GB or 16GB (gigabytes) and work with iTunes to upload songs. ITunes is the iPod default management program which allows you to upload songs to its library, create playlists and sync music on your iPod quickly and easily. This simple process will have you jamming to your favorite songs in no time.


Downloading to an iPod Nano1Connect your iPod Nano to the computer using the USB cable. Launch iTunes if does not automatically launch. When you launch iTunes, it will display your iPod Nano on the left panel.
2Add music to your iTunes library. Click the "File" button on the top menu and click "Add to Library." Locate the song you want to upload to your player and click "Open" to load it to your program.
3Click the "+" button on the lower left panel to create a playlist. Type a name for the playlist and drag the uploaded file to it. To upload additional songs, repeat Step 2 and drag the uploaded additional songs to the created playlist.
4Drag the songs in the playlist up or down to select the order in which the songs will play.
5Sync your iPod Nano. Click the iPod icon on the left panel after importing songs and adding them to the created playlist. Click the "Music" tab and click "Sync music." Click "Select playlists, artists and genres" and select the playlist you created that contains the songs you want to upload. Click "Apply" to automatically sync and download the songs to your iPod Nano.
6Click the "Eject" button and disconnect your iPod from the computer.

Tips & Warnings
Click "Music Store" if you want to purchase a music file. Search for the song on the iTunes store and download it to the iTunes library.

To download songs to iPod nano: m Simply connect iPod nano to your computer. If iPod nano is set to update automatically, the download begins. Important: The first time you connect iPod nano to a computer, a message asks if you want to transfer songs automatically. If you accept, all songs, audiobooks, and other items are deleted from iPod nano and replaced with the songs and other items from that computer. If you don’t accept, you can still download songs to iPod nano manually without deleting any of the songs already on iPod nano. While music is being downloaded from your computer to iPod nano, the iTunes status window shows progress, and the iPod nano icon in the Source list flashes red. When the download is complete, a message in iTunes says “iPod update is complete.” If you set iTunes to download music manually, you can reset it later to update iPod nano automatically. For more information, see “Updating iPod nano Manually” on page 22. To reset iTunes to update iPod nano automatically with all songs and playlists: 1 Open iTunes and select iPod nano in the Source list. 2 Click the Options button and click Music. 3 Select “Automatically update all songs and playlists.” The download begins automatically.
if you need further assistance please let me know. Thanks, MIDWEst-tek

Test the songs that are not playing on the iPod in iTunes and see if the original file is still playable on iTunes if the song still plays re-sync your iPod could be when iTunes copied the song it must have failed or timed out, if that fails re-syncing try restoring you iPod Nano i have had this problem before and I just re-synced and it worked fine!

Green and ORANGE? orange indicates the iPod is searching for music.
UNDERSTAND this- when you play music in the iTunes app., you are hearing the music in your computer not the iPod.
1) Install the latest iTunes application.
2) Do a restore
3) sync your iPod

Did you use iTunes to put the songs on? This is totally essential to being able to see the songs on your iPod. download iTunes here

when you installed itunes did you check the box where it asked you to automatically eject ipod or manually eject?

maybe the you either need two get a new verison of itunes my ipod once wasnt regomize and it was because i needed 2 upgrade the itunes

iPod does not need any drivers only thing you need is iTunes if you dont have iTunes download iTUnes from here and when you connect iPod iTunes will detect it and there you can copy songs and syc play list and songs.

http://www.apple.com/itunes/

OK. Not that I know exactly what your issue is but I can definitely see a problem pattern. Couple of ideas...what are u playing this on...headphones or speakers....change to a different output medium...if you are using the FM transmitter...try it without it...use headphones etc. My thought is perhaps whatever you are playing on is shorted out and possibly sending power back into the ipod causing erratic behavior and/or reboot lockup. Second...clean the entire Ipod (reset to factory) and connect it to a different computer and transfer just ONE song and play it. Let me know about how this works out...i am curious about your issue.

Hello there! Wow... sounds like you've really been through the proverbial wringer with this issue already! You have indeed tried almost every step I would have suggested already, but here's another thing or two to try: 1) Burn an audio CD of this song. It's a true waste of a CD, but fortunately CDs are quite inexpensive! 2) Eject the CD. 3) In iTunes, find the problem song and add something to the title to make it differentiate it... for instance, if the song was, "Freebird", I would rename it, "Freebird CORRUPT". 4) Re-insert the CD, and now rip this new version of the song into iTunes. 5) Sync up your iPod and see if the issue is resolved. Hope this helps you out! =)