no cover pictures appear on ipod classic

Make sure your iPod is enabled to show the artwork:
1. Connect your iPod to your computer
2. Click on the iPod icon when it appears the iTunes Source pane to bring up the preference tabs.
3. Select the Music tab of the iPod settings. The iPod settings are displayed to the right in the main iTunes window.
4. Select the "Display album artwork on your iPod" check box.
5. Click Apply to save the changes. The iPod begins to update as soon as Apply is clicked.

If Zevoneer's tip doesn't help then this might...

*Why is artwork not showing on my iPod when it's there in iTunes?*
iTunes will display a cover in many of it's views provided at least one track from the album has embedded artwork. The iPod appears to load only the artwork from track one to create the cover flow and album views which means that it can sometimes fail to display art for albums even when you can see the art in iTunes. Further, when tracks are played on the iPod, artwork is displayed if and only if it exists in the currently playing track, so track one may show art while track two does not.

*How to find tracks without artwork*
To find all the tracks without artwork so that you can update them you can try http://www.stum.de/itunes-find-tracks-without-artwork/ for Windows or http://dougscripts.com/itunes/scripts/ss.php?sp=trackswithoutartwork for Macs. Use Google, Amazon, Discogs etc. to locate relevant images. Ideally these should be square, 320x320 pixels or above and borderless to give the best results in the various menus. If you have artwork for some tracks of an album, but not others, find the album in the main music folder, select a track with artwork, right-click (Option-Click for Macs) on the art & click copy, then select all the tracks of the album, use CTRL-I or Command-I to *Get Info* and then paste the image into the artwork box.

I say 320x320 because I believe (from using TouchCopy) that it's the size used in the iPod cache so if you're going to crop or resize you might as well work to that size. Otherwise 200x200 is probably good enough.

tt2