How do I fix wrong artwork?

I have an iPhone with about 1,000 songs, a lot of them are singles and not part of any special album. I spent weeks adding artwork to all of them so when I held the phone upright (portrait orientation), when a song played it always showed the right artwork.
Normally when using the iPhone in iPod Touch mode I hold it vertically in what I call Portrait position. I noticed that when I turned the phone sideways - landscape view - that songs not part of an album did not always show the artwork for that song, or just showed a blank grey screen. One day I decided to go through those songs in the album view in iTunes and add artwork to the ones which had no artwork.
Since then almost all my song artwork has gone down the toilet. In portrait view a certain song will play but shows the wrong artwork. If I check the GET INFO feilds in iTunes the right artwork is there but it won't show in the portrait orientation.
BUT, if I turn the phone to landscape view I see the album covers rotate until the right artwork shows. Have I ruined all my hard work or can I undo whatever I did? I am not fussed about the album view, would much prefer to use the phone in portrait view and see the correct artwork which is still in the data field but just not showing.
I am using latest iTunes with Windows xp, on a 1st generation iPhone. NOTE, the program did not give me the choice of listing my hardware as a 1st gen IPhone so I listed it as an ipod touch, the closest option.
thanks
Kim in Australia

Howdy Kathleen,
It sounds like your iPhone is syncing to your library, but seems to be getting stuck on the last step. I would use the troubleshooting in the following article to help you resolve that issue, named:
iTunes: Resolve USB-related alerts
See if the cable connection at the device or computer has come loose or unplugged.
Unplug the cable you're using to connect your iOS device from the USB port on your computer, and then reconnect it. Then unplug it from your iOS device, and reconnect it.
Remove any third-party battery packs or cases from the device and ensure that the USB cable is connected directly to the port on the device.
If your Lightning or 30-pin cable is connected to a keyboard, display or USB hub, try plugging it directly into a USB port on the computer instead.
Close any virtualization apps (such as Parallels or VMWare).
These apps may interfere with your computer's ability to communicate over USB if they aren't properly configured, or up to date. If this resolves the issue, contact the developer of the app to see if an update is available.
Restart your computer.
Restart your iPhone, iPad, or iPod touch.
If you're using an accessory or third-party cable to connect your device, try using an Apple cable with the device instead.
Update to the latest version of iTunes if you haven't already.
Disconnect other USB devices from your computer, except for your keyboard and mouse. Then, reconnect your iOS device. If the issue is resolved, reconnect the other USB devices one at a time. Make sure your iOS device is still recognized by the computer after adding back each device.
If one of these steps resolves the issue, but it comes back later, make sure you haven't changed how the device is connected. For example, check to see if you plugged the device into a specific accessory, or used a specific cable that reintroduced the issue.
Thank you for using Apple Support Communities.
Take care,
Sterling

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