How can I automatically get album covers for music on my ipod?

MediaMonkey should do everything you need. The trick, however, is to "tag" the mp3s with the album art. The next trick is to enable album art display on the iPod. You shouldn't need anything else, and should be all set!

just a thought: try to optimize the pictures as much as possible because they take up space on your iPod. i'm assuming you have a 60GB iPod, but remember you actually only have 55.6 GB of space. personally, i don't see the point of album art unless you have space to burn, and i know i don't. it sound like you don't either.

I use http://www.yvg.com/itunesartimporter.shtml a free program that searches the Amazon database for album covers. I've found it to successfully find the artwok I need about 99.9% of the time. You simply open iTunes and iTunes Art Importer. Select the songs you want to find artwork for in iTunes (easiest to do album at a time), hit the search button and you get a list of possible matches. Select the one you want and hit the import button and voilla the artwork is added to the selected songs.

I used the iTunes Art Importer that mule recommends, but be aware that it requires http://www.microsoft.com/downloads/details.aspx?FamilyID=262d25e3-f589-4842-8157-034d1e7cf3a3&displaylang=en -- which isn't common, I don't think. If you've got something that can work, then stick with it, like twiggy said.

then stick with it, like twiggy said. this gives me the giggles, for some reason. additionally: to optimize album art for your iPod, turn off Album Art in the iPod preferences, and then turn it back on. this should also speed up the UI - large album covers tend to make it sluggish.

FWIW, I've been in the midst of a similar undertaking, but on a Mac. While there are several applications that will assist in this, I've found that they're hit-or-miss with album art, especially with compilations (even when flagged as such). So I've actually wound up doing this manually, using a combination of images.google.com and http://www.slothradio.com/covers/. This gives me the option of choosing which image I want to use. Handy tip if you do this: if you have the album selected in the iTunes library browser, you can drag the image directly from the web browser into the "selected track" cover-art pane and it will apply it to all the tracks (works on the Mac, anyhow). As to size--I think most of the images I've been dredging up have been 30 KB or less. Most of my MP3s are 3 MB and up. So the cover art adds 1% or less to the file size.

...you can drag the image directly from the web browser into the "selected track" cover-art pane and it will apply it to all the tracks (works on the Mac, anyhow). Works on the PC, too.

I have no personal experience with this program, but http://www.ipodsoft.com/index.php?/software/iart is from the same makers of iStory Creator, which is pretty cool.

There's a Konfabulator plugin called "iTunes Companion" that does an amazon image lookup for whatever's playing...