Songs That Teach History

My Mixtape’s A Masterpiece is a weekly feature in which a guest compiles a playlist around some theme. This week, Kiley Fox assembles 12 songs that teach the listener about some historical events. Read Kiley’s thoughts on each song and listen along to the Spotify playlist on top and/or the YouTube playlist at the bottom of the post.

Wreck Of The Edmund Fitzgerald

As a public historian who concentrates on indigenous folk music, the sweet spot for me is songs that tell history. Music is its own emotion and using it to tell these stories is a wonderful way to not only learn history, but to feel it as well. Music is also an incredible learning tool for remembering concepts. Next time you want to learn something that you definitely want to remember, turn it into a song. Or better yet, just listen to this playlist of songs that includes music that either teaches you history straightforwardly or inspires you to research deeper.



1. “Enola Gay” by Orchestra Manoeuvers in the Dark

Much darker than their signature song “If You Leave”, but you wouldn’t know it from the upbeat nature of this jaunty tune. Enola Gay was the name of the bomber that dropped the atomic bomb on Hiroshima. The plane was named after the pilot’s mother and the bomb itself was named Little Boy. Thus the scathing line, “Is mother proud of little boy today?... It’s never ever going to fade away.” This song prompted their manager at the time to threaten to quit if released. They released it anyway.


2. “The Wreck of the Edmund Fitzgerald” by Gordon Lightfoot

Gordon Lightfoot was well known for a catalog of songs that told stories and taught history. After reading about this particular shipwreck, he composed this song, because the tragedy touched him so deeply. The song is mostly factual, but Lightfoot did take a couple liberties for flow. The Fitzgerald was actually headed to Detroit, and there is no evidence the main hatchway gave in. He later changed that line so as not to mislead the public.


3. “Istanbul (Not Constantinople)” by They Might Be Giants

I know it seems silly this one is on the list. Frankly, it is the earliest way I remembered the relationship between the two as a kid. I liken it to how the song “M-I-S-S-I-S-S-I-P-P-I” taught me how to spell Mississippi. Again, it sounds silly, but turning information into a song will help me remember pretty much anything. It is how I taught my kids to memorize my phone number. No, I did not use the “867-5309” tune from Tommy Tutone, though it is amazing how many people remember that number that goes nowhere.

Fall of Constantinople

4. “Dallas, 1pm” by Saxon

This is a classic rock song that still goes hard. It references the assasination of JFK somewhat graphically for a mainstream song. I theorize that it got more leniency, because Saxon is a British metal band, and also due to the fact that JFK was a beloved president. The radio chatter is especially haunting.


5. “The Palace of Versailles” by Al Stewart

Al Stewart loved making political songs. This one about the French Revolution remains unfortunately all too relevant. There is something wonderfully disconcerting about the use of modern synth on a tune based on William Byrd’s “Pavan: The Earl of Salisbury.” It feels almost symbolic of the clash between tradition and the modern needs that outgrow it.

6. “Spanish Bombs” by The Clash

This song was released on the legendary London Calling album. It is artistic, original, and the kind of inspired mess that makes you do your research, because what the hell was Joe Strummer trying to say here? On the surface it is a narrative about the Spanish Civil War from the viewpoint of a nationalist freedom fighter. It also has a chorus sung in Spanish which does not actually make sense with the verses. There is a lot going on in this track. Just as there are a lot of complicated layers to these kinds of uprisings.

Spanish Civil War

7. “Putin” by Randy Newman

People seem to forget about Randy Newman being a passionate activist as well as a tried and true smartass. He has the musicianship of a masterclass composer while having the sense of humor and ego of a jester. He is a national treasure, and “Putin” as well as the accompanying music video is pretty hilarious. It is exactly the kind of thing Putin would probably hate the most. Good for Randy Newman.

8. “American Pie” by Don McLean

You had to know this would be on the list. Let’s talk briefly about it though. A core memory and soul shaping moment for me was when my high school history teacher played this and asked us to list as many possible references to history. Don McLean purposefully made so much of this cryptic and vague so that it could apply to different people and events. What’s most surprising is how much of this song is actually autobiographical and in reference to his childhood and coping with it. I won’t spoil it for you. You can look it up. That’s what learning history is about. No ChatGPT allowed on this assignment either!

9. “The Death of Emmett Till” by Bob Dylan

I have complicated feelings about Bob Dylan, but I believe passionately about his importance to folk music. It’s because of songs like this that tell the truth about the oppression in America that makes me put him up there with the likes of Pete Seeger and Woody Guthrie. This track about the hanging of Emmett Till is one that shouldn’t be forgotten. It’s an injustice we still can’t seem to correct, and one that still plays out every day. If you love Bob Dylan, I recommend Jesse Welles, who I see as his contemporary counterpart.

Funeral of Emmett Till

10. “Join ICE” by Jesse Welles

And here is Jesse Welles. My family, both immediate and extended, are all big fans. He has the cool, calm, and collected swagger of being progressive without being sentimental. His music is the youthful voice we need that reminds us there is no argument. There is right, and there is wrong. Nothing less will do. As for this song, there is a great live performance of it from the The Late Show with Stephen Colbert. This level of shade is the chef's kiss.

11. “Strange Fruit” by Billie Holiday

I’m guessing you see a theme here. The reason being is that history is written by those in power, and it is essential that we keep the voices of the oppressed alive and furious. Music and art is critical to this endeavor. We cannot forget, and we cannot forgive until a change has been made. While made famous by Billie Holiday, this song stems from a poem written by Abel Meeropol about anti-lynching and was published two years before Holiday’s release of the song.

12. “The Triumph of General Ludd” by Chumbawamba

I have included Chumbawamba on a Mixtape list before about hidden revolution songs. They remain one of my favorite bands of all time for their innovation, musicianship, risk taking, and commitment to the resistance. I chose this one from their album English Rebel Songs 1381-1984 in which they cover historical songs of rebellion. This one references the Luddite Rebellion which is often misunderstood as people against the technology of the Industrial Revolution. This is not the case. It is important to note that the rebellion was in protest to the extremely low wages, and abuse of textile workers in trade for inhumane capitalism. The technology was simply the means and the destruction of it was integral to breaking the cycle.



Kiley Fox

When Kiley isn’t laughing at her own terrible puns & dad jokes, she can usually be found studying archaeology, talking about dinosaurs, or watching movies with dinosaurs. Proudly a layman of film, she doesn’t care if you think her opinion sucks. She does however feel it’s important that you agree folded over chips are the best chips.

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Summerween 2026