Playlist not downloaded correctly?

I recently ripped 7 CD's into iTunes and am subscribed to iTunes Match. I put all the CDs into a playlist but now that list looks and acts differently than other playlists. The songs will play individually when clicked but will not play one after the other as a playlist.

The faulty list looks like this:

And a "normal" playlist looks like this:

What's wrong and how can I fix it?

Thanks