Hi Alex_h1,
Thanks for replying. To answer your question, no - it does not only happen when the title of the album is the same as the band. I'm annoyed with myself that I used that screenshot because I realized its a poor representation of this issue. To be clear, further down the playlist, there were other albums by Crosby, Stills & Nash titled Deja Vu, Daylight Again, etc. and the issue was still present. It's either the whole playlist, or not at all.
On that note, I also confirmed this issue happened whether the playlist had different band names (like a compilation) within the playlist, or if the entire playlist is made up of albums of the same band name (typed exactly the same). So it was truly random.
However, as an update, I went into iTunes > View > Show View Options > Changed "View As" to "Songs", unchecked "Album" and then the album title stopped appearing under the song title name (on ALL playlists throughout iTunes).
But I'm still curious why it did it in the first place. Truthfully, I like it better with the album name in grey text under the song title. I just don't know how to get it back. Searching online, I only found one other person sharing the same experience, but no one replied to his post.
Any thoughts?