Learning Succinct Storytelling from Pop Songs

The best complete story arcs in four minutes or less.

Lately I’ve been taking a break from nonfiction book writing after finishing Parks and Rec (out April 7!). Instead, I’ve been indulging my creativity by playing more music, even attempting to write a few songs, and writing fiction. This has made me think more about the incredibly efficient way that some songs tell entire stories in just a few short minutes.

The songs I’m highlighting here span from the ‘70s to recent years, and, well, all of them except one are romantic stories. And even the one that isn’t is a … rather intense relationship. I guess romance is simply a surefire story engine. It’s actually a challenge to come up with a novel or a song that doesn’t have some element of relationship drama.

I’m a lyrics person, so I love everyone from Fountains of Wayne to Chappell Roan, Eminem to Taylor Swift. All of them have written their share of story songs, which by definition keep us listening to hear what happens next. Here are some of my favorites:

“Escape (The Pina Colada Song)” by Rupert Holmes

Okay, there are a lot of weird things here, most notably that this is a 1979 song, which means that I was 3 when it came out, and somehow it registers as one of the first/the actual first story songs that ever hit for me. I guess I was just hearing it when I was a little older, though I’m still fascinated by the fact that adultery and adult beverages rang so true for me so early. In any case, this tells the story of a guy (am I sure it’s a guy? anyway, it’a guy’s voice singing) who places a personal ad looking to cheat and ends up, O’Henry style, getting his ad answered by his own wife, or answering his own wife’s ad. Aww, I guess? The ‘70s were a weird time. I still fucking love this song, even though I am literally training to be a yoga teacher and one of the main lines is, “If you’re not into yoga, if you have half a brain …” I guess specifics get me every time. It’s also funny to me that I quoted this song in my online dating profile that led me to meet my partner of 15 years, Jesse.

“Fast Car” by Tracy Chapman

Chapman’s 1988 masterpiece re-emerged in mainstream culture a few years ago thanks to a loving 2023 cover by Luke Combs. We return to it for good reason. Three-act structure? You got it: “You got a fast car, I want a ticket to anywhere/Maybe we can make a deal, maybe together we can get somewhere.” Next: “You got a fast car, we go cruising to entertain ourselves/You still ain’t got a job, and I work in the market as a checkout girl.” And finally: “You got a fast car, I got a job that pays all our bills/
You stay out drinking late at the bar, see more of your friends than you do your kids.” So, she sings, “You can take your fast car and keep on driving.” Hetero-pessimism in full swing folks.

And yet, still, she returns to the refrain, remembering driving in the car when “I had a feeling that I belonged,” and “I had a feeling I could be someone, be someone, be someone.” Anyone else cry a little every time they think hard about that lyric?

“Good Luck, Babe!” by Chappell Roan

You just know when the opening lines are, “It’s fine, it’s cool,” that it is neither fine nor cool. I love an opening line that implies “things are not right here” without explaining everything. We soon have conflict, right in the build-up to the chorus: “I don’t wanna call it off, but you don’t wanna call it love.” And then we get to that soaring chorus, a.k.a. the thesis statement: You, whoever you might be, can kiss a hundred boys in bars—a lot of boys, a perfect image—but you, madam, “would have to stop the world just to stop the feeling.” This is high drama. The bridge, however, has the absolute showstopper of a scene: “When you wake up next to him in the middle of the night, with your head in your hands, you’re nothing more than his wife …” followed by the soft, then loud, “You know I hate to say, but I told you so!” I absolutely love a good dynamic delivery.

“All Too Well” by Taylor Swift

I won’t exactly say that I prefer the original five-plus-minute version to the epic 10-minute 2021 release as part of Swift’s re-recording of her album Red. What I will say is that a five-minute version has to be pretty great to excite folks about a twice-as-long version nearly a decade later. My god, the scarf in the first verse that she leaves at her lover’s sister’s house shows up again in the end: “But you keep my old scarf from that very first week/’Cause it reminds you of innocence/And it smells like me.” (Chekhov would be proud!) Indelible images accumulate like a freeway crash pileup: singing in the car getting lost upstate, he almost runs the red because he’s looking at her, the mom telling stories about him on the T-ball team, dancing ‘round the kitchen in the refrigerator light … all until “you call me up again just to break me like a promise.” It’s too real not to be about a specific somebody. A Google search will tell you the likely (famous) culprit if you don’t already know.

“Betty” by Taylor Swift

I could do an all-Swift list about storytelling, but I’m picking my two favorites here. “Betty” is part of a teen-love-triangle trilogy on the Folklore album, and while “August” is my favorite of those musically, “Betty” lays out the story the best. In it, a kid named James has wronged his love, Betty—”would you trust me if I told you it was just a summer thing?” Betty has found out from “the rumors from Inez, you can’t believe a word she says most times, but this time it was true … the worst thing that I ever did was what I did to you.” James builds all of this up through chorus repetitions: “But if I just showed up at your party, would you have me, would you want me? Would you tell me to go fuck myself or lead me to the garden?” What is going to happen at the party?

I never fail to get chills when Taylor-as-James brings her delivery down a bit quieter at, “So I showed up at your party … yeah, I showed up at your party,” then explodes into a key change: “Yeah I showed up at your party, will you have me, will you want me, will you kiss me on the porch in front of all your stupid friends?” OH MY GOD WE’LL NEVER REALLY KNOW, at least in my interpretation. He asks a lot of questions that aren’t really answered, except with what I see as a memory, or a hope: “Standin’ in your cardigan, kissing in my car again, stopped at a streetlight, you know I miss you.” He still misses her at the end! Was it all a reverie? Did he show up and did it go poorly? It’s all very Before Sunrise. The song “Cardigan” may or may not answer these questions, and I love that we can all have our own theories. But really, don’t miss out on “August,” which tells the story from Ms. Summer Fling’s devastating perspective. “Cancelled my plans just in case you’d call, back when I was living for the hope of it all … meet me behind the mall.”

“Hackensack” by Fountains of Wayne

One of this excellent band’s strong points was always storytelling. Their most famous song is “Stacy’s Mom,” a compact little narrative you don’t forget once you’ve heard it. But I prefer this dreamy ode to a former classmate who got famous. Can you beat this first verse?:

I used to know you when we were young
You were in all my dreams
We sat together in Period One
Fridays at 8:15
Now I see your face in the strangest places
Movies and magazines
I saw you talking to Christopher Walken
On my TV screen

Perfect details, I am fully seated and waiting to hear what comes next. R.I.P. to one of the great songwriters, Adam Schlesinger.

“Stan” by Eminem

Jesse and I recently re-listened to this song on a long car ride, and the new Apple Music update had defaulted my playlists to crossfade from one song to the next like a DJ. This if fairly dumb and annoying to me, but the point in this particular post is that it means that the ends of songs often fade out and get usurped by the next song before they really finish. Even though we’ve both heard this song countless times, we gasped when it cut off before the big reveal: “Come to think about it, his name was … it was you. Damn.” That’s some storytelling. Eminem builds it up in epistolary form, reading from a series of letters from a fan named Stan as his messages grow increasingly disturbed, possessive, agitated, threatening, and, finally, violent. Showing and not telling to the greatest effect.