Playlist will not shuffle new songs I add to it

[mattgoold]

I keep a playlist of my favorite albums from the year and I listen to it on shuffle when I drive. Recently I've run into a problem where the playlist will NEVER play the songs from the latest album I added. I can't make sense of it and I'm losing my mind. Everything else works fine, shuffles everything else seemingly randomly and evenly, just completely omits the songs as if they were not on the playlist.