Andrew Listens to... the Five Greatest Stories in Songs (feat. John MacGaffey)
It's a bold statement to call out The Greatest in any field, but John makes a compelling argument for why these songs are iconic for their narrative value.
John: Despite loving poetry, I often struggle to pay attention to the lyrics of songs, so when Andrew asked me to write a guest post for his blog, I figured this would be a great opportunity to dive into the words of some of the best songs out there.
To lean as far into this as possible, I decided to write about the best stories found in popular music. It's an open-ended prompt, so to further narrow it, I wanted to also consider cultural impact and importance; as a proxy for this I chose to limit myself to Rolling Stone's "500 Greatest Songs of All Time (linked)."
The stories found in these songs are deeply moving – their themes speak to universal experiences that resonate across generations. They're all decades old, and their staying power is a testament to their craft.
Andrew: John is one of the most intentional music listeners that I know. And his blog (linked) was an early inspiration into starting my own. So I’ve been very excited to see what music we’d be listening to together. Of course with John there’s a balance of subjective feelings and quantifiable metrics. Keeping an eye on both the personal impact of these songs and their cultural weight is a very John approach. The list that he’s curated are all iconic narrative songs, capturing a half century of popular music and across 6 different genres. I think what pops the most for me is that all of these songs touch on the loneliness and yearning that come with being unsatisfied. I wonder what other stories fit that feeling.
Let's dive in:
Andrew Listens to…The Five Greatest Stories in Songs (Linked to Spotify)
Eleanor Rigby by The Beatles
The Boxer by Simon and Garfunkel
Fast Car by Tracy Chapman
Jolene by Dolly Parton
Mr. Brightside by The Killers
Piano Man by Billy Joel [Bonus]
John: Written by Paul McCartney, "Eleanor Rigby" tells the story of two characters, the titular woman and Father McKenzie. The opening line, pulled from the chorus and repeated twice, leaves little ambiguity regarding the song's theme: "Ah, look at all the lonely people."
In the first verse, we're introduced to Eleanor, who "lives in a dream" and is "picking up rice in a church where a wedding has been." Eleanor wasn't part of this wedding, and the backdrop of a recent, happy celebration provides contrast to her isolation.
She's "wearing the face that she keeps in a jar by the door," which incidentally was inspired by McCartney's mom's propensity for wearing a lot of Nivea cold cream (linked). However, in the context of the song, it serves as the metaphorical emotional mask Eleanor wears when she's out in public, presumably to conceal her underlying loneliness.
The chorus returns us to the opening line, but this time asks the listener two haunting questions:
All the lonely people
Where do they all come from?
All the lonely people
Where do they all belong?
We're then dropped into a new scene with Father McKenzie, who's "writing the words of a sermon that no one will hear." It's an emotional portrait of a man who's dedicated himself to religious community, but doesn't even have a congregation to preach to.
In the third and final verse, the two characters intersect, but under tragic circumstances. Eleanor died in the church with no family and not even a single person to witness the burial that Father McKenzie provides her.
Notably underscored by a string octet, the song provides commentary of urban alienation and the quiet sadness of loneliness. And in doing so, it shines a light on the forgotten and unloved members of our society.
Andrew: I love “Eleanor Rigby”. I went through a big Beatles phase in middle and high school and played a lot of Beatles covers on the piano. Of the whole Beatles discography, I’ve always had a soft spot in my heart for Revolver and how its saturated and budding experimental sound demonstrates an inflection point in their career. From that album, Eleanor Rigby was a real stand out. As John said, this three part exploration of the lonely and forgotten people paints a poignant picture, especially the third stanza, where the two lonely characters meet. But even then Eleanor has already passed and the priest is still alone. I’ve also always been interested in the lines from the song about Eleanor waiting at the window and picking up the rice in the church. It’s as if Eleanor is always at a level of remove from the events that she dreams about. Similarly, the image of Father McKenzie standing at his pulpit in an empty sanctuary. The tragedy perhaps is not just the loneliness, but how trapped these characters are at their level of remove, always desiring, but never changing.
John: "The Boxer" is a semi-autobiographical song by Paul Simon, written in response to feeling unfairly criticized by critics who were attacking his reputation in the late 60s.
Continuing with the theme of loneliness from our first song, it's a first-person narrative about a poor man navigating isolation in New York City. He's "laying low, seeking out the poorer quarters / where the ragged people go / looking for the places only they would know."
In the third verse, we learn that our narrator isn't getting any job offers, occasionally seeking comfort from "the whores on Seventh Avenue."
Omitted from the studio recording but included in the original composition and performed live, the fourth verse remarks on the passage of time:
Now the years are rolling by me
They are rocking easily
I am older than I once was
And younger than I’ll be
But that’s not unusual
This obvious observation is followed by a reflection:
No, it isn’t strange
After changes upon changes
We are more or less the same
There's room for interpretation here, but I hear this verse as an optimistic turning point in the song; even amidst hardship, there is something enduring about ourselves.
The narrator then expresses an urge to go home, "where the New York City winters aren't bleeding me," but then resolves to stay, metaphorically assuming the character of the boxer. He's battered, angry and ashamed, crying out "I am leaving," "but the fighter still remains."
The song represents facing adversity and obstacles in pursuit of something better. Its raw frustration, punctuated by the wordless chorus of "lie-la-lies" (originally a placeholder but ultimately left in), speaks to our capacity for resilience.
As such, it was a hauntingly beautiful choice for viewers tuning into the first episode of SNL after 9/11, which featured Paul Simon performing it (linked) live.
Andrew: To me “The Boxer” will always be inseparably linked to the movie “Midnight Cowboy” which came out the same year. In both cases, a young man leaves his home to come to the big city to make his fortune/escape his past, but is met with the reality of freezing winters, destitute conditions, and the growing realization that if he doesn’t leave, he will die. Also, both pieces point to the function of sex workers to provide comfort to the desperate, but show how abused these people are in the big unfeeling cities. “The Boxer” ends with the metaphor of the fighter in the ring, shouting out that “I am leaving, I am leaving” but still remaining. The unnamed protagonist of the song, like Eleanor and Father McKenzie, is trapped, yearning for release from the abuses of being alive, but unable to make the changes that would affect that freedom. In this case, perhaps this reluctance to move is romanticized. It’s heroic to take the blows and keep standing up. .
John: Tracy Chapman's 1988 hit "Fast Car" also speaks to fighting adversity, focusing on a woman trying to overcome the cycle of poverty. The song is addressed to her partner, whom she hopes can help. It opens:
You got a fast car
I want a ticket to anywhere
Maybe we can make a deal
Maybe together we can get somewhere
Any place is better
That last line is heartbreaking — she's in the worst place she can imagine, with "nothing to lose."
The second verse fantasizes about their future life: "You and I can both get jobs / And finally see what it means to be living."
We learn that the narrator quit school to care for an alcoholic father who says "his body's too old for working," but "his body's too young to look like this" — an arresting image. Her mom left her dad because "she wanted more from life than he could give."
The song then takes on a sense of urgency, repeating the opening line and asking if the car is "fast enough so we can fly away," followed by "we gotta make a decision / leave tonight or live and die this way."
The two decide to leave, and our narrator becomes optimistic: "I had a feeling that I belonged / I had a feeling I could be someone." And indeed she starts to, getting a job that pays all the bills, but her partner ends up spending more time at the bar than with their kids.
The final verse echoes earlier refrains, both lyrically and narratively, ending in confrontation:
You got a fast car
Is it fast enough so you can fly away?
You gotta make a decision
Leave tonight or live and die this way
It's a devastating conclusion, and the song musically never strays from its simple composition, letting the story speak for itself.
36 years after its release, the song made headlines in 2024 after Chapman and country singer Luke Combs performed it together at the Grammy's. Combs' cover of the song had become a hit the previous year, and the joint performance served as a beautiful tribute to Chapman.
Though Chapman won Best Female Pop Vocal Performance at the Grammys in 1989, Combs' cover led the Country Music Association to award her Song of the Year, the first time a Black artist has received that distinction.
When reflecting on the racial implications of that moment, it's hard not to think about Beyoncé's album "Cowboy Carter," with its commentary on genre definitions and the under-recognized contributions of Black artists in American culture.
But the enduring popularity of "Fast Car" only further cements Chapman's legacy as a brilliant songwriter and her ability to simultaneously speak to persistent economic inequality and the timeless yearning for something more.
Andrew: I was first introduced to “Fast Car” in my junior English class, which was built around American Literature, and the song was played as an example of the American Dream. That term “American Dream” was coined in 1931 by James Truslow Adams to describe how social, intellectual, and financial mobility were what made America different from the rigid social structures of Europe. This idea that every person has the ability to “make it” if they try has been called the national ethos. In literature however, many canon writers attempt to discredit or pick apart this idea, such as Steinbeck, Miller, and Carlin. In this song, Chapman is in the same conversation. Starting from zero, she’s hoping together they can make something. And the song follows their attempts to achieve that American Dream, for her to get promoted and move to a bigger house in the suburbs. But in the last stanza, we see that even when they achieve that upperward mobility, they’re still unhappy. In the end, all the mobility and achieved stability didn’t bring fulfillment or happiness, even when the Dream has been achieved. So was the Dream ever worth it? Is there a way to reach fulfillment? Chapman leaves us no answers, just waits unmoving on the precipice. Again, our protagonist yearns but is unable to move (“I got no plans, I ain’t going nowhere”). But then we’re left repeating the chorus, the memory of the joyful escape, with a loved one's arm wrapped around the shoulder and the feeling that she could be someone.
John: Dolly Parton's 1973 hit single "Jolene" cuts to the chase in its opening line: "Jolene, Jolene, Jolene, Jolene / I'm beggin' of you, please don't take my man."
Inspired by a bank teller (linked) who was flirting with Parton's husband, the song tells the story of a woman begging Jolene not to take her man. She pleads, "Please don't take him just because you can."
Our narrator is deeply threatened by the other woman, describing her striking appearance of "flaming locks of auburn hair" and "ivory skin and eyes of emerald green."
The song is about jealousy, insecurity, and feelings of inadequacy — particularly in the context of a close romantic relationship. The nuance of the narrator's appeal provides depth to an otherwise simple narrative. Rather than become enraged at Jolene, she asks for her compassion:
He's the only one for me, Jolene
I had to have this talk with you
My happiness depends on you
Though we're left without a resolution and never learn Jolene's response, the real-life bank teller never stole Dolly Parton's husband Dean, who stayed married to her until his passing earlier this year (linked).
Ultimately, the song's haunting melody, vulnerability, and catchy repetition earn it recognition from Rolling Stone as the #1 country hit of all time (linked).
Andrew: John conjured Cowboy Carter earlier in this review, but I want to bring her back to talk about “Jolene”. Beyonce performs a barnburning interpretation of the Dolly Parton stand by, in which she threatens to bring the heat against the seductress, declares that it would take more than “beauty and seductive stares” to “come between a family and a happy man” and that Jolene’s peace depends on her stepping off her man. While it’s a defiant and empowering declaration, it’s hard to take seriously when Jay-Z’s proven infidelities inspired Beyonce’s Magnum Opus, “Lemonade”. And in those cases, Jay-Z was not a seduced victim, but an active participant in the breaking of his vows. The queen doth protest too much by making the “other woman” the villain against her innocent victim of a husband. And ultimately this brings us back to the power in the original song, which is that Dolly Parton is helpless. She’s begging Jolene to not pursue her husband because Dolly cannot compete, with evidence that her husband has already fallen in love, talking about her in his sleep and calling out her name. It’s a deeply vulnerable song to write and in that way a universal experience for the listeners. The helplessness in the face of jealousy and the yearning to make it alright by just explaining what you need. In this way, Dolly’s helplessness is different from McCartney, Simon, and Chapman, in that at least she’s trying to do something. In the face of an impossible situation, she tries.
John: In the introduction to this post, I wrote that all of these songs are decades old. Reader, I regret to report that The Killers' 2003 song "Mr. Brightside," does in fact qualify for that distinction.
Setting aside the relentless march of time and the reminder from "The Boxer" that "I am older than I once was," it goes without saying that "Mr. Brightside" is in the upper echelon of songs that can get millennials screaming lyrics at the top of their lungs.
Similar to "Jolene," "Mr. Brightside" is also based on a true story and narratively short. The Killers' frontman Brandon Flowers wrote it after catching his girlfriend cheating on him in Vegas. Emotionally, it's the inverse of "Jolene," filled with rage. There are no asks for compassion here, just a dizzying panic:
Now I'm falling asleep
And she's calling a cab
While he's havin' a smoke
And she's taking a drag
Now they're goin' to bed
And my stomach is sick
The song earns its place on this list with the way its short lines cement its impact by reflecting a nearly hyperventilating narrator's state. Taking frequent short breaths to sing along to it, you can't help but start to feel an inkling of the narrator's anxiety.
He continues to spiral:
And it's all in my head,
But she's touching his
Chest now
He takes off her dress now
Let me go
And I just can't look, it's killing me
The song's repetition, broken up by a single verse ("Swimming through sick lullabies / Choking on your alibis"), only further underscores the narrator's vicious rumination. It's palpable.
But despite, or perhaps because of its repetition, "Mr. Brightside" continues to captivate listeners. Last year, it became the third most popular song of all time in the UK based on combined purchases and streams.
Andrew: “Mr. Brightside” is a song that confounds understanding. How does a song that couldn’t break the top 100 for the first year of its existence end up in the Guinness Book of World Records for being the longest charting song in UK history (416 weeks) and be crowned the Anthem of a Generation by the New York Times. In 2023, journalist Jessica M. Goldstein wrote, “If boomers gave the masses “Don’t Stop Believin’,” millennials can claim “Mr. Brightside” as the generation’s official entry into that canon”. And it’s a song about finding out you’re being cheated on and absolutely losing it. Compared to the other songs on this list, it’s a remarkably simple conceit. But damn if Brandon Flowers doesn’t perfectly encapsulate those feelings in their most palpable form. Like Parton, Flowers taps into a universal fear, the sense of panic that sets in when it turns out that the world as you know it is built on a lie. And needing to continue being a person while that world collapses around you. I’ve never been cheated on, but when I belt this song as karaoke, it bears the weight of every unrealized jealous thought or anxious worry. And, coming back to the theme, “Mr.Brightside” ends with Flowers singing, “I never/ I never”. It’s another moment of arrested movement, of indecision and being trapped. Even as Flowers feels that destiny is calling him, he waits.
[A Bonus Song]
John: I had to include one extra song on this list — the one that inspired the premise of this post in the first place. When I decided to limit the songs I could pull from to Rolling Stone's list I was dismayed to discover that Billy Joel's "Piano Man" wasn't included.
Instead they chose Joel's "Scenes from an Italian Restaurant." It's also a great song, but it pales in comparison to the character study in "Piano Man."
Released in 1973 and based on Joel's experiences as a performer, it tells the story of a crowd of regulars entering a bar from the perspective of the piano player.
I'm known among my friend group for playing this at parties at 9 o'clock on a Saturday, since it's the opening line of the song.
The narrator proceeds to evocatively describe a whole cast of characters, including the "old man sittin' next to me / Makin' love to his tonic and gin" and John at the bar who's "quick with a joke or to light up your smoke / But there's some place that he'd rather be."
In the chorus, the regulars implore our narrator to entertain them:
Sing us a song, you're the piano man
Sing us a song tonight
Well, we're all in the mood for a melody
And you've got us feelin' alright
But despite the piano man lifting patrons' spirits, there's a sense of melancholy throughout the song, and we return again to the theme of isolation found in "Eleanor Rigby" and "The Boxer": "They're sharing a drink they call loneliness / But it's better than drinkin' alone."
Just like the piano man's music boosts the mood of his listeners in the song, it's hard not to feel similarly "alright" singing along to it with friends.
Joel's masterpiece may not be recognized by Rolling Stone, but its inclusion in the Grammy's hall of fame (linked) and the Library of Congress' National Recording Registry (linked) more than make up for it.
Andrew: I’m so glad that John made an exception to his rule and included “Piano Man” to this list. It’s a song that lives very dear to my heart for many reasons. I was introduced to the song in my sophomore year of high school, when Veronica, one of our school’s piano prodigies, approached me about doing it as a duet for a school assembly. More shocking was that she didn’t want to play the piano, but rather the harmonica while I played the piano part. I learned it and practiced it a thousand times, so that I wouldn’t embarrass myself or Veronica. Unfortunately I stopped taking lessons soon afterwards, but for years, if I found a piano in the wild, I would sit down and play “Piano Man” note for note. After years of feeling like a failure as a pianist, it felt good to have this instantly iconic song in my back pocket. Years later, it became a friend group standby, played at house parties and weddings alike as we all stood in a circle and belted our faces off (some more harmoniously than others). And in between verses we’d gossip about whether the bar was a gay club (it isn’t canonically, but it should be). And I think what makes it so powerful is that it’s almost diegetic. We are singing with Billy Joel in the same way as his regular, and thus we become his regulars. And all of us have to contemplate that all of the regulars in the song are caught in their own ways: the almost movie star, the almost novelist, the almost politician, the businessmen slowly getting stoned. Then we have to ask ourselves, if we are also regulars, are we also trapped in our own stories? Are we going after the things that would bring us satisfaction, or are we trapped at the threshold, unwilling or unable to go through. But then Joel tells us that we’re sharing a drink called loneliness, but it’s better than drinking alone. So maybe, ultimately, the feeling of pause is a human fact of life, but if we can be in community in those moments, then maybe we don’t have to feel alone.
I want to thank John for this incredible gift of music and for his insightful commentary.
Next time: Andrew Listens to… Summer Jams