The Top 20 Pop/Rock Songs About or Inspired by Literature (Pt. I)

As ranked by moi

Let’s have some fun. A while back, I did a post on the best history based pop/rock songs of all time. That post came from listening to songs that had some basis in history, and ranking them both on their quality but also on their “historical” content. I found it a bit of work to do, since there are not that many songs based on history among rockers (understandably), but I did wind up discovering a number of really good songs in the process.

In hopes of repeating my success, I decided to dive into the world of pop/rock songs inspired by or about literature or literary characters. Literature and music have a much more direct link, as you may imagine, and though I knew of a few songs inspired by great literature, I knew there must be much more out there. And I was right.

For the top historical songs, I had a pretty rigid criteria as to what counted as “historical,” but with literature the connection is much more loose. My criteria for this list will take into account the relationship to the source material and the quality of the music, but also the quality of the lyrics—not only how well they use their literary inspiration but how inventive and satisfying they are. I make no claim to inclusiveness, or comprehensiveness; I found most of these song through internet searches save for a few songs. So feel free to contradict me in the comments and suggest songs that I missed. Let’s begin!

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20. The Doors, End of the Night (1967)

This is a really weird song, from a really weird guy in Jim Morrison. In reality, the song was written early the band’s history, about 1965. Morrison’s lyrics sound pretty much like some sort of psychedelic experience, unsurprisingly. The song’s title takes its inspiration from a novel by the French writer Louis-Ferdinand Celine, Journey to the End of the Night, a semi-autobiographical novel which ends with a murder and the narrator lamenting that he could not find “one single idea…far stronger than death.” Besides this lovely bit, Morrison also pilfered part of the song’s lyrics from the poet William Blake. The line "some are born to sweet delight; some are born to endless night" he took Blake’s 1803 poem "Auguries of Innocence." The song is very strange, but that psychedelic tone coheres with its lyrics so well that it makes it worthy of inclusion.

19. Metallica, For Whom the Bell Tolls (1984)

I am the first to admit I don’t like Heavy Metal that much. But one thing I learned researching this list and my one on historical songs is that many of them have been written by metal bands. The two bands who kept showing up on these lists were Steely Dan (whom we’ll hear from in due time), and Iron Maiden. Actually, Iron Maiden probably had more songs on both lists than any other band, but I just don’t like their music that much. Metallica, however, I can listen to *occasionally*. This song derives its inspiration from Hemingway’s novel of the Spanish Civil War, For Whom the Bell Tolls, and its lyrics describe the death of five soldiers trying to hold a hill, depicted in chapter 27 of the novel. They are not the best lyrics I’ve ever heard, but they depict the death of the men in pretty stark, brutal terms, which I found impressive. Also, it is a killer song.

18. David Bowie, We Are the Dead (1974)

Bowie’s 1974 album Diamond Dogs contains three songs inspired by George Orwell’s dystopian novel 1984, and “We Are the Dead” is one of them. Bowie at one point thought of adapting the novel (as a musical?) and these songs were the result. The lyrics of '“We Are the Dead” are written from the perspective of Winston and Julia, the characters whose doomed love is portrayed by Orwell. The song is eerie and the music hypnotic, but for some reason I thought the lyrics were a bit long-winded and didn’t fit together with the music as well as the other 1984-inspired songs on the album. Hence it comes in at seventeen.

17. Lana del Rey, Off to the Races (2012)

This is one artist I admit I never listened to before compiling this list, and though I found the song artfully done, I can understand why I never did before. Lana del Rey’s “Off to the Races” is an homage to Vladimir Nabokov’s controversial novel Lolita, about an old professor who seduces and exploits a very young teenage girl. Now, the term “lolita” has been universalized to mean any sexually active young girl, but del Rey specifically cites the novel itself, clipping the line “light of my life/fire of my loins” directly from the novel. (This is not the only song inspired by Nabokov on the album Born to Die, as there is another titled Lolitaas as well, that I did not find musically nearly as satisfying.) Okay, it’s creepy—call it pedophile Pop—but it is very well done in an artistic sense The song’s quasi-R&B sound combines with the teenage persona with which del Rey sings almost perfectly. And it is a very imaginative rendering of the novel, for whatever it’s worth. But yes, I am going to take a shower now.

16. Led Zeppelin, Ramble On (1969)

Led Zeppelin appears on this list a second time, again for a song that at least took some inspiration from a work of literature—the same work of literature, Lord of the Rings. The song comes from Led Zeppelin II, and its lyrics are mostly about a man who is leaving a woman to find another woman—not exactly the best story for references to “But Gollum and the evil one/Crept up and slipped away with her.” Reportedly, Robert Plant admitted in interviews to being embarrassed about the references, but when you are Led Zeppelin, nobody cares. Or at least I don’t. The song is so good and the direct references to LOTR have it at fifteen on my list.

15. Dire Straits, Romeo and Juliet (1980)

In my search for songs with literary themes/inspiration, I thought I would find a lot more references to the Bard, but they were far fewer than I would have guessed. Perhaps I didn’t search in the right places, but the best song in terms of music I could find was this lovely ballad by Mark Knopfler and Dire Straits. However, the lyrics are fairly pedestrian by my lights, and turn the story of the two “star-crossed lovers” into standard American English without much charm. (I know some people like Shakespeare turned into “street” English but they are WRONG.) Hence, this is as high as a song about the Bard goes on my list.

14. Cream, Tales of Brave Ulysses (1967)

The work of literature that came up the most in my search for literary songs was without question Homer’s Odyssey. (The Iliad came up a lot as well, though not as much.) The quest of Odysseus has fascinated many an author over the centuries, from Dante to Lord Tennyson, and there are even two films out or in production on The Odyssey as I write this. This song from the 60s supergroup Cream comes from their album Disraeli Gears, its marriage of psychedelic rock with lyrics that play up Odysseus’ seduction at the hands of Calypso makes for a literary classic. Psychedelics and literature seem together, as this is the second song which fits that mold on my list—but not the highest on this list.

13. David Bowie, Big Brother (1974)

The second Orwell inspired song on this list, Bowie’s “Big Brother” takes a haunting, sort of operatic song and fuses it with a sardonic take in which people clamor for “Big Brother” instead of fearing him:

Please saviour, saviour, show us
Hear me, I'm graphically yours
Someone to claim us, someone to follow
Someone to shame us, some brave Apollo
Someone to fool us, someone like you
We want you, Big Brother, Big Brother

The song is amazing, and uses the idea of “Big Brother” in an inventive way, but as satire it is a bit on the nose. Hence it just misses the top ten by a few slots.

12. Alan Parsons Project, The Cask of Amontillado

The Alan Parsons Project is another artist whose work I am not familiar with, but their 1976 debut Tales of Terror and Imagination: Edgar Allan Poe, is worthy of praise for its putting the works of Edgar Allan Poe into the pop music genre in inventive ways. The album features several song which channel more or less directly the mind of the morbid Poe, and of those on the album, “The Cask of Amontillado” is my favorite because of its haunting lyrics and use of grand synthesizer walls of sound that give it something of an operatic feel. The lyrics are haunting, if not spectacular, as they tell things from the perspective of Montresor, the narrator of Poe’s story.

11. Tori Amos, Jamaica Inn

Tori Amos is another artist I don’t often listen to much, but I found “Jamaica Inn” a charming and reflective use of literary inspiration. Jamaica Inn is the title of a novel by Daphne Du Maurier, in which a weekend at a hotel in Cornwall turns into an encounter with smugglers and unsavory local characters. The song picks this up and turns it into a melancholy of regret, making reference to Du Maurier’s most famous novel, Rebecca:

The sexiest thing is trust
I wake up to find the pirates have come
Tying up along your coast
How was I to know the pirates have come
Between Rebecca's

Beneath your firmaments
I have worshipped
In the Jamaica Inn
In the Jamaica Inn

The combination of wistfulness and lyricism means you don’t have to know much about the literary background to enjoy the song, something Amos noted in an interview. That combination makes it just outside the top ten.

10. The Cure, Killing an Arab

Yet another artist I don’t often listen to, The Cure’s “Killing an Arab” starts off our top literary songs of all time with a banger inspired by Albert Camus’s existentialist novel The Stranger, in which—spoiler alert—the protagonist kills an Arab. The novel became controversial as a result, apparently because critics don’t read, but the novel itself is about the indeterminate nature of one’s actions and choices (Camus was an existentialist, after all). I am not the biggest punk fan, obviously, but the song’s driving rhythm and moody lyrics make a great combination, exemplifying Camus’s dread perfectly:

Staring down the barrel
At the Arab on the ground
To see his open mouth
But I hear no sound

I'm alive
I'm dead
I'm the stranger
Killing an Arab

It’s that unity of music and lyrics I am looking for, even if these words aren’t exactly poetry.

9. Jefferson Airplane, White Rabbit (1967)

You knew this was coming, right? Jefferson Airplane’s evocation of Lewis Carroll’s Alice in Wonderland as a not-too-thinly-veiled—if veiled at all—allusion to psychedelic drug use or at least to strange experiences, is the probably the best use of literature in pop music for that purpose:

When logic and proportion
Have fallen sloppy dead
And the White Knight is talking backwards
And the Red Queen's off with her head
Remember what the dormouse said
Feed your head
Feed your head

Grace Slick’s vocals are subtle and powerful by turns, and the drumrolling, march like beat of the song make it a shoe-in for the top ten on my list, and you could argue it should be higher.

8. Jimmy Buffett, The Ballad of Skip Wiley

Does Jimmy Buffett really merit a place on this list? After all, didn’t he just write the same song over and over again? And the inspiration for his song—Carl Hiassen’s Tourist Season, a novel in which the protagonist decides that the only way to preserve Florida’s natural beauty was to start killing tourists—does that really count as “literature”? Didn’t the poet Wallace Stevens compare the state to a “venereal” mistress because of its dubious charms? Isn’t Jimmy Buffett just the musical incarnation of “Florida Man”? In short, why include him on this list?

Answer: I’m from Florida, and because fuck you.

Seriously though, “The Ballad of Skip Wiley” is a great song, wonderfully produced, and does in fact capture something of the seedy, roguish nature of the state, echoing the idea of “ballads” and folk songs of disreputable figures:

He was last seen atop of a mangrove
Perched like a wounded osprey
He was not meant to last
He belongs to the past And I hope he gets there one day

He's crazy and dangerous
But who else can you trust
He's the outlaw in all of us
The environmental terrorist

Buffett didn’t have much of a repertoire in terms of range, but what he did well, he did very well. The lyrics match the music perfectly, and most of all, in a list of songs that are normally very ambitious and kind of heavy, “The Ballad of Skip Wiley” is, above all, FUN. May the late Mr. Buffett be singing it somewhere over Jordan.

The countdown will continue in a future post, when we will discuss the rest of the top ten, as well as some honorable mentions, and reveal the Number 1 Literary Geek Song of All Time! Stay Tuned!