The assignment: Imagine you’re talking to someone who’s never heard your favorite artist. Create a playlist that doesn’t just introduce their music, but exemplifies why you love them.
The rules: You’re limited to:
- Five songs.
- Deep cuts.
- No covers.
- No live recordings.
The reason we’re doing this: Hey, why not!
The idea for these Deep Five playlists popped into my head when I wrote my Indigo Girls tribute a while ago. It wasn’t easy, but it forced me to relisten1 to, reconsider, and rediscover their music.
I really enjoyed the thought experience, so I invited others to do it as well. Here are the results.
Indigo Girls
By yours truly
Midnight Oil
By the Complimentary Spouse
Crowded House
Also by the Complimentary Spouse
Billy Joel
By Randi
Bruce Springsteen
By Eric2
Hey Dave, Where Are the Explanations?
I’ve deliberately left them out. The goal is for the listener to go into the playlist without anyone else’s commentary or ideas influencing the experience.
Deep Cut Footnotes
- Not a real word. It should be. ↩︎
- Eric had a good question when I invited him to do this: What counts as a deep cut? It’s a subjective term and, as Eric pointed out, hard to nail down for an artist whose catalog is as big as Springsteen’s. I hadn’t really thought about any criteria, so I said that if it feels like a deep cut to you, it’s a deep cut. I also told him not to overthink things, which is rich coming from me, as I am the King of Overthinking. ↩︎

