What does disappointment taste like? (but make it music)

A little backstory before the backstory

As I was writing and writing and rabbit-holing and delighting in discoveries for this edition of the newsletter, I realized that part of my passion for this topic isn’t just because sad songs help us gin up resilience when all seems lost. They do, yes. But also, I’m a writer and stand in awe at the craft of songwriters. While so much pain is squirreled away in our personal lives, songwriters resist the human urge to sweep pain into the dimly lit corners of our souls’ alleys and side streets.

But also, I’ve worked in music-adjacent industries for a decade—the GRAMMYs and Nokia’s music team forming a platform that was a regional-music-centric competitor to Apple’s iTunes, not to mention that many, many of my friends work in the actual music industry at labels or as music supervisors or executives or repping songwriters or even the founder of a songwriting school; then in my family, music is quite important with many relatives who are or were musicians and eclectic disc jockeys for cool indie radio stations. All of which is to say, with a network like this, I look at songs through a variety of lenses. This is not a “best of,” list and what I’ve gathered below is in no way definitive nor assembled with a “professional’s take.” This is me hunting and gathering ideals and fodder for good conversations I wish I could have with you, here. (With that in mind, feel free to share your personal faves in the comments.)

This post is about how powerful songs can sweep us away. The words and melodies that we connect with are so personal. Just one line can do it.

As you’ll see, this all started as an exercise to exorcise the pain of disappointment. And what I ended up with is a treatise on the power of putting word to pain, an homage to the magic of songwriting as a form of resilience, and a tour of a few of the greats who do it so well.

The Actual Backstory

A few weeks ago my sister-in-law told me that my 9-year-old niece experiencing true (9-year-old level) devastation when she learned that she would have to travel for a family wedding on the last day of Harry Potter camp.

Disappointment and Fear of Missing Out is so new at nine years old.

We’re just starting to understand choices and obligations and trade offs and all the BS that paves the way into our boring, disappointing adulthoods. At that age, it’s more than disappointing, it’s a heartbreak. In the adult world, it’s like missing out on a long-awaited wedding of a friend because of an unavoidable last minute work trip. (Or insert whatever painful adult moment has been a giant disappointment to you.)

I don’t have a child near this age and don’t know how to navigate the emotions of children with the capacity of speech,¹ but that doesn’t mean I don’t have ideas! (This is the exact kind of “helpful” advice that parents hate. I know this.)

But I really thought it might help my highly creative niece who is also a Taylor Swift fan; so I offered a suggestion: name the pain.

Maybe if she could name what she was feeling, she could accept it and move on from it. …Not just name it but describe it. Give it shape and color and texture and temperature. Bring that pain out of you and give it a separate life. Let The Pain be its own being. Give it form so that it is separate from you, so that you can see it for the radiating mass that it is, and so that you can ultimately free it.

Maybe she could get so absorbed in creating this avatar of her sadness, that she wouldn’t actually feel the sadness anymore.

In my own experience, disappointment washes over us with the power of a riptide, buffeting us back and forth, back and forth, between states of sorrow, so maybe giving shape to the emotional mass signals a release valve and we begin to recover from the anguish of a missed opportunity.

Maybe seeing The Pain as a separate entity helps us usher it out the door faster, before it becomes a toxic serum that gradually metabolizes into our emotional cellular network. …maybe.

Clearly, I was quite taken with this thought starter: what does disappointment feel like, look like, smell like? I kept thinking about how songwriters make beautiful the ugly; creating anthems to torment that ultimately help us all metabolize the poison of misery just a little bit faster.

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Photo by Lucas K on Unsplash

Originally, the title for this newsletter was going to be WWTD: What Would Taylor Do?

Appealing to my 9-year-old niece, I wanted to connect the dots for her in a sphere she understood: Taylor Swift lyrics.

While I have immense respect for Taylor’s considerable talent as a songwriter…and performer…and businesswoman, I’m not a Swiftie. I can’t immediately call to mind her cannon, but I don’t think she has one about Harry Potter camp.

But, boy, what fodder would missing the ultimate day of HP camp would have been for an early TS original. We can all guess that a younger Taylor would have assembled perfect words for the feeling of missing out on the thing that we really wanted.

In the world of Fierce Resilience, if I had a workbook with exercises for getting through hard times, this would be a chapter assignment: give your sadness an avatar. Give it a shape and form and let that be separate from you.

But in the weeks since this moment with the Harry Potter camp revelation, I kept thinking about those who do this so well. The pros. The songwriters who aren’t Taylor Swift (oh, them). And so the question that I started chewing on for myself is much bigger (and maybe it’s questions, plural), like: Why does pain feel better when we sing along to it? Why do we love having our hearts ripped out by music? And why (oh why) do sad songs seem to save our souls?

Instead of pretending like I have an academic answer, let’s take a tour through some of the best, some of the most popular, and some surprising sad songs that just work when we need them to.

Starting here.

If you’re looking for THE LIST, here’s one. This is based on a poll of 2,000 adults, and from what I can tell it was not assembled from any actual authority on music (so, all those friends and family I mentioned before, please feel free to write me back or add a comment because we’d love to hear your takes!).

But that list above is pretty solid. It has the big hitters on there like I Will Always Love You (by Whitney but I choose Dolly), Nothing Compares 2U (Sinead O’Connor, written by Prince), and topping the list, Everybody Hurts (R.E.M.). Some of the songs in this list are thematically sad but—to me—don’t necessarily evoke deep emotion. Boyz II Men’s End of the Road? Sure, sad, but it sits in a “nowhere zone” between more nuanced songwriting that evokes a personal sense memory and a banger we can wail to. By being neither, it doesn’t really hit my “sad song” criteria.²

The list below isn’t just my personal choices for sad songs. I rooted around the internet to see what lyrics provide solace for others going through tough times. But since I started this newsletter with Taylor Swift, I’ll start this list with her too…

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1. Exile - Taylor Swift ft. Bon Iver

As previously mentioned, I am not a Swiftie and therefore do not have innate knowledge of her cannon, but I do replay a few of her songs (currently it’s Cruel Summer for dancing with my toddler). Exile is one of those on repeat. A duet with Bon Iver,’s Justin Vernon is sung from the points of view of ex-lovers who see each other out one night. The harmony and lyrics make it very re-playable and irresistible to sing along to. (See the aside below.) The two sets of lyrics are sung over each other, mimicking an argument in slow-motion as each side replies in frustration before the other is even finished speaking. I know those arguments. Maybe you do, too. The anger, hurt and tension of those real life moments are palpable in this song.

An aside: I should take this opportunity to share that I’m a big singer. Not just a shower singer and obviously not like a professional singer, but I am the type of person who would (or has on multiple occasions) rent out a karaoke room with just one other person (or myself) to sing. I’ve also karaoke’d on very public stages and—more than once—chosen a song to sing in front of an audience that I had no business singing, to disastrous result. And I don’t care. Which means I’m also the kind of person with a list of songs in my phone to “practice” singing to….in all my spare time as a new mom. (But we shan’t let karaoke dreams wither on the vine!) All of which is to say — I like to sing, a lot. And that has influenced some of the songs chosen for this list.

So, yes, Exile wormed it’s way into my heart for the sake of it’s sing-ability, but ALSO, it nails that feeling of unresolved emotions hanging heavy between two people who are looking back just a little to see where it all went wrong and still speaking in the weaponized tones that lovers do when they start to grate on each other as the relationship starts to crack/ has cracked. This is on the list for its blisteringly realness of the complexity of a relationship dissolving; the ickiness of no clean resolution or break from the emotional fog.

(Another aside: this newsletter’s research took me down some really fun research wormholes; such as — Reaction Videos on YouTube. It turns out that my hope for these was grander than the actual quality of most of them, but I did enjoy this one. A youngish male YouTuber in a white t-shirt, tats and flat-brimmed White Sox hat. It seems that Swift is not within his normal genres but he’s diving in to listen for the first time. I loved the moment (@ 5:09) when he pauses in heavy reflection and gravitas to say, “I don’t think I’ve ever seen anybody write break up songs like Taylor Swift. Taylor Swift and Eminem.”

Well, true. And why are we not talking about that pair of songwriters more?! Have they collaborated? (Turns out even Yahoo! Entertainment asked this.) Will they? Did Taylor Swift perform an acoustic version of Eminem’s Lose Yourself in 2011? Yes.

But sadly there is no Em in this list.

Next up…

2. Soon You’ll Get Better - Taylor Swift

So, when I started researching just exactly what *would* Taylor Swift do to describe pain and sadness, I discovered a song she wrote about her mother’s cancer. Talk about putting words to your emotions and allowing for a much needed catharsis…

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This whole idea for the list and the suggestion — WWTD — came from a subconscious desire to explore the talent and toil of the songwriting profession because songwriters do our dirty work. They pick apart the hard parts of life, the moments we wish would pass us quickly, and assemble them into language our souls understand. Lyricism and melodies make it easier on us to both identify with the pain and to move on from it.

The College Years

3. Between The Bars - Elliot Smith

Earlier I talked about naming The Pain and giving it form and separation, which is Elliot Smith’s liberating and a heart-wrenching tactic in Between the Bars, where he speaks to alcohol as a person, that thing that’s helping push life away, push away the person he could have been and mute the person he is. As he loses the battle with addiction, he heels the freeing sensation of alcohol, telling him that he’ll be safe—away from who he is. “It’s literally a depiction of addiction itself seducing the addicted… it’s your drug of choice whispering in your ear.” (Redditor @Olelander)
The song’s moodiness hangs with the weight of despair.

Drink up with me now
And forget all about the pressure of days
Do what I say and I'll make you okay
And drive them away
The images stuck in your head

People you've been before
That you don't want around anymore
That push and shove and won't bend to your will
I'll keep them still

Smith’s real life pain was turned into beauty that helped me explore nuanced emotion in my college years. Helpful in that effort was the Good Will Hunting soundtrack on repeat in my CD player (yooo), and its six(!) Elliott Smith songs. (Not familiar with the soundtrack? It’s an eclectic smörgåsbord of B-side³ bangers.)

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4. Brick - Ben Folds

Hi, we’re back in my college era with Ben Folds’ most popular song, Brick.

Guys, let’s set the scene: a kid from North Carolina got his high school girlfriend pregnant and in 1997 he puts out an album that includes a song about it.
He. wrote. out. the. moments. leading. to. a. day-after-christmas, early-morning abortion.

Bold.

This is not a female take, with a point of view on pain or regret or sadness or relief. From the male view, it is detached yet soulful. Evocative yet observational. He wrote the thing that was happening, what he did not want to experience but had to. There are moments in life when we want to be anywhere else than where we are. There are times when we would pay anything to be in an alternate reality.

As a human, we may not be able to physically be anywhere else than in the situation we find ourselves in, but a songwriter uses their powers to transmute the pain for the rest of us. To help us all feel less alone.

A little more about Ben Folds’ unflinching ability to pull out the emotional Big Guns in an interview for Tidal: You went through some rough stuff, from a car accident to a girlfriend’s abortion. Did you decide early on in your music career that you’d tackle gnarly topics with humor and wit?

BF: Nah, I just really wanted to write good songs. And you can feel how much better a song can be sometimes when it has the momentum of truth behind it. Once you’ve done that and it’s a good song, it’s hard to take back. You can change a couple of names to protect the innocent, or change anything you want. It’s creative. But the feeling behind it should be honest. And it’s easier to do that if you’re evoking your own memories.

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Speaking of songs from the era of my formative years, let’s dial it back to the deep grunge era and a song Eddie Vedder wrote as he drove from San Diego to Seattle that landed on Pearl Jam’s debut album, Ten …

5. Black - Pearl Jam

There are many songs about angst from the grunge era but few that rip me up like Black.

If you really need to belt out some emotions, save your energy for the last few two lines and then just give it all up to the grunge power ballad gods.

I know someday you'll have a beautiful life, I know you'll be a star
In somebody else's sky, but why, why, whyyyyyyyyyy
Can't it be, can't it be mine

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A Surprising Choice

Someone, many people in fact, could/should criticize me for adding the next song to the line up, after a beloved Pearl Jam jam. But here it goes—I’m just going to say it: the modern, pop version of Black is…

6. Someone You Loved - Lewis Capaldi

Could it be called a cheesy pop song? Yes. But sheesh, if this had been out when I was going through a breakup⁴, it would have SLAYED ME. Also, the sing-ability is HIGH.

I was not planning to put this on the list, only include it as a casual parenthetical because it feels a little too modern and slick to be in the Cannon of Sadness, but I just re-listened and I’m giving it an actual place on the list. Because, it still rips my heart out, hitting a very specific moment of longing. (Remember in the video above I mention all the ways we humans try to ignore our emotions? Forgot to put, “dating someone” on the list.)

I guess I kinda liked the way you numbed all the pain
…I let my guard down
And then you pulled the rug
I was getting kinda used to being someone you loved

“I was getting kinda used to being someone you loved” HITS because you know the feeling of losing the thing you were afraid to lose just as you were getting confident in not losing it. It’s our old frenemie, vulnerability, biting us in the ass.

And THEN I dare you to watch the music video. Guys, I’m still crying.⁵

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”I’ll f*cking do it, darling.”

Talk about a heart-ripper.

7. The Show Must Go On - Queen

As I mentioned earlier, this newsletter isn’t just a listicle of personal tear-jerkers I play when I’m feeling down. I rooted around for a variety of songwriters who pull sadness’s venom from our hearts by putting their own hearts on the line.

Looking up the saddest songs on Reddit gave me some good ideas, one of them that never would have come to mind, The Show Must Go On by Queen. A little wikipedia journalism (Pulitzer, here I come) confirmed that, yep, this is an evisceratingly real moment captured, just barely:

It [The Show Must Go On] is credited to Queen, but was primarily written by guitarist Brian May.^[link] The song chronicles the effort of frontman Freddie Mercury continuing to perform despite approaching the end of his life, although his diagnosis with HIV/AIDS had not yet been made public in spite of ongoing media speculation that he was seriously ill.^[link] When the band recorded the song in 1990, Mercury's condition had deteriorated to the point that May had concerns as to whether he was physically capable of singing it. May recalls; "I said, 'Fred, I don't know if this is going to be possible to sing.' And he went, 'I'll fucking do it, darling'—vodka down—and went in and killed it, completely lacerated that vocal."⁶

(See the footnotes for a note on this video⁷)

And there you have it, the first half of my list of Songs that Rip Your Heart Open. I told you it was going to be random!

As I mentioned in the video above, I’d love to hear your thoughts. Leave a comment on social, write me back here, make a comment on Substack. I want to hear what songs break your heart only to mend it again.

And, when in doubt, consider, “I’ll fucking do it, darling” as the answer.

Until next time, xxM

1. My daughter is 18 months old. We’ve nailed crying and tantrums but not a discourse.

2. There is no criteria and this is a very imperfect list. Which is what makes it fun to assemble.

3. I’m sure that many of the tracks were not actually b-sides but the alliteration was too good to pass up. Music peeps, correct me!

4. Ok, so there is dispute what inspired this song. On one hand Lewis says he wrote it about his grandmother dying AND NOT his ex-girlfriend who went on reality TV and told everyone that this song was about her. I’m really rooting for her not to be the genesis of this for the sake of her being, as I can see, sorta rude to him. But also, it’s pretty hard to listen to this and not imagine a romantic situation rather than a grandparent dying.

5. This initial version of the video was made in partnership with a UK charity for organ donation. It’s a fantastic brand collaboration but knowing that it was driven with that lens makes me aware of all the emotional buttons it’s pushing. Survey says: I’m ok with it.

6. A note on resilience; 'I'll fucking do it, darling' is my new fucking battle cry.

7. From the YouTube Creator (@VinzA) who made this video: “What if The Show Must Go On had been performed live... Queen's last tours were in 1986 while The Show Must Go On was recorded in 1990, 1 year before Freddie Mercury's death. So this song has unfortunately never been played live ... To make this clip I needed 153 shots from Live Hungarian Rhapsody and a lot of patience;)” Bravo to VinzA! This took work!