The second-saddest song of all timelines is “Dancing on My Own” by Robyn. Disagree? That’s cool, but you’re wrong. Want to physically fight me about it? Sure. Whatever. Get in line. Before we start throwing ‘bows though, hear me out.

It’s a song about regret, we can agree on that, right? The track opens with its speaker posted up alone in a Swedish discotheque, where she happens across a recent ex; it’s immediately clear she’s still in love with this person. Clad in a weird, bright feather-vest (per the now-infamous music video), Robyn dances like a woman possessed, like she’s fending something off. But that’s because she is.

          I’m in the corner, watching you kiss her, oh oh oh
          I’m right over here, why can’t you see me, oh oh oh
          I’m giving it my all, but I’m not the girl you’re taking home, ooh
          I keep dancing on my own

On the surface, there’s really nothing special about these lines. By the end of the song, though, it’s clear that’s something’s missing, and it’s something we really want to know: what exactly caused this relationship to fail?

We’re never given a forthright answer. After taking in the entire track, though—Robyn’s lunatic dance moves, her insistent, uncomfortable voyeurism—an answer begins to take shape, at least implicitly: She blames herself.

There’s a quiet wistfulness in the song, a distance from and respect for her ex-lover’s situation that, to me, an esteemed scholar of Norwegian dance-pop, implies that the speaker feels responsible for her relationship ending.

And this is where the real weight of sadness enters. Breakups suck. So does being racked with guilt and self-blame. Honestly, though, I think we all get that, and have since we were like 11 years old. “Dancing on My Own” is so affecting not because of what the song is about, but because of how Robyn handles it. The singer’s futility, but more importantly her inability to come to terms with it head-on, to speak its name, is what breaks my heart.

She has to turn away. She has to.

Enter Bonnie Raitt, whose music was the initial inspiration for this labyrinth, Harry-Potter-hedge-maze-at-the-TriWizard-Tourney of an essay.

You’ve probably heard “Nick of Time,” the title track from her lauded 10th studio album (also the name of a terrible 90s political thriller starring Johnny Depp—lots of sorrow there, too). It’s an initially woeful, anxiety-ridden meditation on the monolithic progression of time, how age overtakes us all, wholly and unrelenting.

In the song’s final verse, though, all of that changes. On the cusp of hopelessness, Raitt is rescued. “Just when I thought I’d had enough / And all my tears were shed,” she sings, “I found love, baby / Love in the nick of time.” And then there are fireworks, a wedding, etc. You get it. The song ends happily.

Question: So you’re saying a song that resolves itself and is actually really uplifting is the saddest thing you’ve ever heard?

Answer: Yup.

Hold on to your kids and pets, people, this take is hot enough to burn.

No, I don’t despair in the happiness of others. At least not all the time. And even though the last movement in “Nick of Time” is ostensibly one of total reconciliation, this doesn’t change just how devastating it is to me.

Ok, so the structure of the song is straightforward enough—there are three verses, a bridge, a few brief refrains, and a chorus. I’ve told you enough about the last one, but her first two verses are the ones worth talking about—complicated and bleak and strange—these are the ones that eviscerate me.

Raitt opens with “A friend of mine she cries at night / And calls me on the phone / She sees babies everywhere she goes / And she wants one of her own.” The friend’s fear, ultimately, is that she will soon be too old to have the child she so desperately wants: “She’s scared, scared she’ll run out of time.”

On a purely narrative level, this verse is pretty affecting. For me, though, the real suffering in these lines comes from somewhere else. Before spelling this out (because that would be too easy and I prefer sticking it to the man), it’s worth taking a look at the next verse in the song, since the pair enforces each other, and both work in the same way.

Next, the singer turns to her parents. “I see my folks, they’re getting old / And I watch their bodies change,” she says. The same refrain marks the end of this verse as well, a singular line standing by itself: “Scared to run out of time.”

So I have this friend, right. It’s not me. No, really, it’s not me. But he, I mean she, has this weird rash on her foot, and I’m wondering, for her, which anti-fungal cream works best.

If you heard me say this, you would be next to certain that I had a weird rash on my foot. It’s the oldest, and worst, deception technique that exists. In my mind, when Bonnie Raitt talks about the fears of her friend, and the deterioration of her parents, she’s actually talking about herself.

It’s no coincidence, then, that the last verse of the song is explicitly about the singer. “Just when I thought I’d had enough / And all my tears were shed,” it starts, “You came along and showed me / How to leave it all behind / You opened up my heart again / And then to my surprise / I found love, baby / Love in the nick of time.” This erases any doubt to me that all of the earlier fears expressed belong to Raitt more than anyone else.

When this first occurred to me, I was wrecked.

I had heard “Nick of Time” before, but really hadn’t paid much attention to it. To be honest, this essay started about Raitt and the complicated image of Americana, and it would have turned out fine. Like being caught in a thunderstorm I didn’t see coming, though, I was overwhelmed by something bigger than me. I was soaking wet and I didn’t want to be.

I’m ashamed of a lot of things, and I have a lot of insecurities, too. For the most part I’m too afraid to admit them. This could be because I care too much about how people think of me, I’m not actually sure. My job, for example, is one of them. As a freelance writer, it sometimes feels like I’m not actually employed. That’s hard for me to admit, and it makes me self-conscious, especially when I’m surrounded by so many passionate, ultra-successful people my same age.

So often I just won’t talk about it, that is, until something good happens. I recently started writing for a well-known local publication, interviewing high-profile visual artists and writing about their work. I love doing it, and it’s respectable in my mind, so of course I’ll bring this up in conversation.

This is very likely just projection on my part, but I see this entire complex playing itself out in “Nick of Time.” Be it from shame, or fear, or both, Raitt addresses her real fears, but does so behind a paper mask. Only in the end, when things find a neat resolution, does she come out and claim success.

At this point I should clarify: I fully believe Robyn and Bonnie Raitt are aware of what they're doing, and the speakers in their songs are personas—in literary terms, the unreliable narrator. Whether or not they're intended to represent themselves or meant to depict a complicated and painfully human emotional complex, I can't say.

What I can say, though, is that both of these songs represent something important in the realm of the ballad. Sad music is my thing. Ask anyone: sometimes I will actually bench press while listening to the Sun Kil Moon's cover of "Ocean Breathes Salty."

While it's impossible to say what exactly draws us to melancholy music, one thing is for sure: there is so much of it that sucks. Without throwing out names like Hawthorne Heights or Aerosmith, I'll say that there are probably at least 100 terrible sad songs for each one worth listening to.

Music is music, though, so a lot of this is way too subjective and visceral to understand, but there's something special, and something definite, about these two. Here's what I know. The actual content of a ballad is endlessly repeated: lost love, death, uncertainty. We've heard it all.

For me, what's more important than showing suffering in these tracks is showing how suffering is dealt with. And honestly, it's not pretty.

It's full of self-deceit and insecurity, of people not knowing how to face difficulty, so they turn away. It's painfully vulnerable. It's human. It's so meaningful to me because I've handled difficulty this same way, and I'll probably continue to.

For example, right now, I’m thinking of excuses to give my old friends about why I can’t go to our ten-year high school reunion this year, since running into that weird kid who’s now a NASA engineer doesn’t sound particularly appealing. Here’s a list of the good ones: car problems, copperhead bite, too many people ask for my autograph whenever I go back home.

Yeah, they’re all actually terrible, and this is probably a pretty bad way of dealing with a problem, but at least I guess I can admit that now.

—Jack McLaughlin