What song lyric do you find most haunting?

I happily introduced my significant other to the gentle, heartbroken music of folk crooner Sufjan Stevens back when we first started dating, but there’s one song she absolutely refuses to listen to with me: “John Wayne Gacy Jr.,” off of Stevens’ 2005 masterpiece Illinois. Our conflict boils down largely to a single line, which comes after two verses of describing the famed serial killer’s troubled childhood, and the terrible things he did as an adult: “And in my best behavior, I am really just like him.” Throughout the song, Stevens—an avowed Christian—refuses to condemn Gacy, or paint him as a monster, but it’s in those final moments that he pushes his empathy, and his self-loathing, to their limits, suggesting that there’s less separating him—or the listener—from a man who killed and raped more than 30 boys and young men than we might like. I’ve thought about that line a lot over the years, imagining the human moments when Gacy could maybe float above the forces that drove him to commit his crimes and just feel cranky, or tired, or happy, like the rest of us. My partner is less of a solipsist than I am, though, and thinks that level of empathy does a disservice to all the people Gacy hurt. She’s right enough that, these days, I usually just hit “skip” and move on to the bouncy rhythms of “Jacksonville.” But that doesn’t mean Stevens’ damning self-assessment isn’t still lodged deep inside my head. [William Hughes]

I like sad songs. Always have. There’s nothing more satisfying than blasting some real depressing music at 3 a.m. and just wallowing in the pain of existence, you know? All of which is to say, there are many sad songs I love very much that could have answered this question. But I’m going to go with one of the all-timers, a lyric that reduced an entire theater to awestruck silence when I saw it played live: “But don’t hate her when she gets up to leave.” That’s the last line of the last song on Neutral Milk Hotel’s 1998 classic In The Aeroplane Over The Sea, an album with some of the most poignantly written lyrics of its decade, if not all time. The entire album is a swirling morass of emotions: Singer Jeff Mangum touches on lust and loneliness, joy and grief, and longing for that which you know you can never have, all in a weird, dense metaphor about being in love with Anne Frank. The final song, “Two-Headed Boy Part 2,” lifts those human impulses up into the realm of the spiritual, positing that the unrequited love that has been torturing Mangum throughout the album is actually something holy. The “her” could be a lover, or it could be God herself, but either way, she’s given Mangum a transcendent gift. Her departure—and the fact that she was ever there at all—should be cause for gratitude, not bitterness. It’s a line I think about a lot. And, in case you’re wondering, I blubbered like a baby at that show, and loved every second of it. [Katie Rife]

I’ve mentally run through enough sad-bastard favorites from enough sad-bastard artists to fill a dozen pathetically transparent mix CDs for a dozen uninterested parties, but I keep circling back to one of the simplest and most plainly stated: “They want you or they don’t / Say yes.” I’ve always been struck dumb and/or tearful by the dual meaning of the two Elliott Smith lines that provide the title to Either/Or’s hushed coda, a resignation and a plea in one: “They want you or they don’t say yes”/ “They want you or they don’t—say yes.” From its title on down, Either/Or details these liminal states, and they’re especially affecting if you first hear them when you’re just starting to learn that other people get caught in overthinker’s limbo, too. It’s a poetry that Smith was singularly adept at, rendered relatable by the vulnerability of his voice and the bedside-intimacy of the production. I’m writing this on the first Monday after the end of daylight saving time; it’s only 5:42 p.m., but the sun seemingly went down hours ago and the whole world feels like “Say Yes.” [Erik Adams]

I feel like there’s a whole lifetime of experience captured in the abrupt opening lyric for Talking Head’s “Crosseyed And Painless.” “Lost my shape, trying to act casual,” David Byrne barks out with no preamble. While it’s not explicitly spooky, I’d qualify this as my most haunting song lyric inasmuch as it follows me around constantly. It pops into my brain with nearly every social interaction I have with someone who isn’t friends or family. It presents this idea that the amount of force you exert to appear like something resembling a regular ol’ human being grinds away at you until the whole structure falls apart. It’s not like I hate talking with people. Far from it! But due to my Gollum-like subterranean predilections, idle and utterly insignificant chats require a ridiculous amount of energy for me. It’s a constant triangulation of jokes (too many?), self-deprecation (“Ease up, you sound like a mope”), and just shutting up to be present. But lest that all sounds too negative, it’s worth remembering that Byrne has made a career of capturing sharp-edged alienation and pairing it with upbeat funk wave, which is a good reminder that there’s still harmony amid the dissonance. [Nick Wanserski]

Even thinking about it now, nearly 15 years after I first heard the song, I still get instant goosebumps just remembering listening to TV On The Radio’s “Dreams,” with its earnest lament “But you were my favorite moment / Of our dead century.” As with most songs, context is everything: The track rumbles along like a mourner’s cry, the key theme being how “all your dreams are over now, and all your wings have fallen down.” It’s an elegy of sorts for someone too blind and cruel to see the harm they’re doing, a common-enough idea for a song. But what elevates it into something beautiful—what haunts me, in other words—is the unexpected touch of love, the admission that for all their faults, this unnamed other was still the “favorite moment,” a testament to how love and connection overrides rational or pragmatic thought. It’s a stirring reminder of the impossible-to-separate mix of care and frustration that often attends our strongest relationships, and it just kills me, every time. [Alex McLevy]

A teen-pregnancy horror story more haunting than Bruce Springsteen’s “The River” has yet to be written. My friends and I were thrilled to get his double album in high school, finding instant favorites in “Out In The Street” and “The Ties That Bind.” Then toward the end of side two, right after “I Wanna Marry You,” things took a decidedly dark turn, as bleak as Bruce ever got (yes, even more so than Nebraska). A teenaged hormone-fueled couple heads out for some late-night visits at the river, until “I got Mary pregnant / And man that was all she wrote / For my 19th birthday I got a union card and a wedding coat.” The couple quickly slides into lower-class monotony, as the economy fails and construction jobs are hard to find: “Now I just act like I don’t remember / And Mary acts like she don’t care.” Then the narrator flashes back to the perfect summer evenings that landed him in the situation he’s in, the river representing all his youthful hopes and aspirations: “Is a dream a lie if it don’t come true / Or is it something worse.” Although the song is reportedly Springsteen’s tribute to his (still-married) sister and brother-in-law, the story of young dreams derailed by circumstance, as the song itself puts it, “still haunts me like a curse.” [Gwen Ihnat]