This has been bothering me for some time now, but it was one of those things that I just learned to live with. I’ve found in the past that it can be difficult to know what search term to enter into Google to find solutions for problems such as these.

So, what is the problem? I have a smart playlist that includes everything from my library, barring podcasts and audiobooks, that has a playcount of 0. As the tracks changed, the album art in the lower left-hand corner did not update. I would have to select iTunes and hit Ctrl L to select the track that was playing and have the album art update.

I decided today to try a quick search and entered this into Google: [itunes play shuffle album art doesn’t display].

That quickly led me to this post at macosxhints, whence I found another related post entitled
See album art for music in a shared iTunes library.

It says:

If you click on the top bar of the little album art window in the corner, and change it from “Selected Item” to “Now Playing”, you’ll be able to see artwork from the shared libraries as it plays. This has been working in iTunes for a few versions already, although it’s a bit hard to expose this functionality.

Here’s a screenshot showing the two options.

It’s just a small thing, but it had been annoying me for such a long time and it’s nice to have it finally resolved. Seemingly it will work with shared libraries too, although I haven’t tested that out yet.