20. Sufjan Stevens “All the Trees of the Field Will Clap Their Hands”
Our boy Sufjan, long before he was infamously ruining everyone with “Carrie & Lowell” in 2015! At the time I thought this was a (still kinda bummed-out) romantic love song. Turns out it was about religion, so yeah, just take your pick as to which of those makes you cry more now.
19. Stars “Your Ex-Lover Is Dead”
Maximalist, almost overture-esque heartbreak staple, straight out of your AIM away message. “Live through this and you won’t look back.” We would never! Right? Setting ourselves on fire does sound pretty appealing, though.
18. Calexico “Black Heart”
The ideal soundtrack for a creepy dusty horror movie set in the most desolate desert — or checking your student loan balance 15 years out of college.
17. Ra Ra Riot “Can You Tell”
Now you might think that the track immediately preceding this one, called “Dying Is Fine,” would be the album’s saddest song. Nah, it’s this one, all about unrequited love. You know, this seems like a good time to take a little break to just casually check on that guy I spent several years in my 20s hopelessly pining for, hold on.
16. Wilco “Ashes of American Flags”
Kids, listen up. Before the iconic Wilco was “dad music,” they were considered indie. Hip. Young. And now, more than 20 years since it came out, “Yankee Hotel Foxtrot” remains the decade’s defining album on isolation and general bleakness. With this song, you can also think about $3.63 Coke/cigarettes and finally understand inflation.
15. Modest Mouse “The Good Times Are Killing Me”
“Hey!” you say. “I just want to listen to this upbeat song without thinking about its ominous undercurrent or how my friend who introduced me to Modest Mouse’s music actually did sadly die from causes somewhat similar to the lyrics.” No. The answer is no, you cannot do that. You can go listen to “Float On” next if you want, at least.
14. Band of Horses “The Funeral”
Retired hipsters might think they’re indifferent to this song at this point, now that it’s appeared in just about every TV show in existence in the 17 years since it came out. Go watch the music video again and read the YouTube comments and get back to me.
13. Damien Rice “Cannonball”
“Cannonball” was somehow always playing on the radio when my alarm went off. Imagine waking to “Love, it taught me to lie/Life, it taught me to die” and then trudging off to your Shakespeare elective. Then imagine telling people now that you’re old enough to have had a clock radio in college — and that you majored in English. Ouch.
12. Jolie Holland “Black Stars”
Lyrics like “When you arrived it was as if we had both died” and “Blood bleeding red like my guitar” feel like they’re straight out of a 2000s emo song. Same effect, just in slow bluesy folk form alongside songs about the Civil War and morphine.
11. The National “Fake Empire”
Oh, you thought this song about trying to mentally escape from an overwhelmingly bad world as you first entered adulthood felt relevant in 2007, but maybe things would get better? That’s cute.
10. Emily Haines & the Soft Skeleton “Crowd Surf Off A Cliff”
This entire gorgeous piano-driven album proves you don’t need a lot of big dramatic guitars or a furious tempo to get those tears flowing. Failed love and failing at life, it’s a classic two-for-one!
9. Sparklehorse “It’s A Wonderful Life”
By this point we hope you could figure out that a song called “It’s a Wonderful Life” wasn’t going to be genuinely uplifting. This gorgeously sluggish waltz from the late Mark Linkous paints an abstract, aching picture while actually being written to address critics who accused him of writing too-depressing lyrics. Whoa, meta.
8. Death Cab for Cutie “Title and Registration”
Brace yourself, we’re entering … top 8 territory. It’s like a MySpace top 8 but there are no friends and instead, you just listen to music and cry in the rain as you look through your car’s glove compartment. In all honesty, we could do an entire 50-song ranking just of Death Cab songs. On the other hand, please don’t give my editor any ideas.
7. Neko Case “I Wish I Was the Moon”
The perfect song for a long, achingly pensive nighttime drive, now and then, though you’ll feel the “I’m so tired” on a dozen levels in your bones now. Please make sure to pull over when the road is blurred out by tears. Your nighttime vision already isn’t what it used to be. Have you gotten checked for astigmatism?
6. Elliott Smith “Better Be Quiet Now”
Welp (remember back then when everyone said “welp”?), this was inevitable in the sad indie category. A lot of the late, great Elliott Smith’s most raw and crushing music was released in the ‘90s, making it ineligible for this ranking but, rest assured, still fully eligible for your general sad listening needs. This underrated song from 2000 hits deep, whether it’s soundtracking a breakup, pandemic-era isolation, addiction, or just sitting around thinking too hard on a Sunday night. Hey, this whole playlist hasn’t been fun for us either over here!
5. Rilo Kiley “A Man / Me / Then Jim”
You already know a song from a noted emotionally devastating band that opens with an anecdote about someone who “hung himself with string” is not gonna be a good time. But that mournful slide guitar and “gradual descent into a life you never meant” in the chorus will continue to haunt you the most.
4. Bright Eyes “Sunrise, Sunset”
Again, an artist with many, many options for this list, but something about the “Fiddler on the Roof” intro to the jolt of the frenetic wail here still trips that claustrophobic inner despair button every time. And let’s just say if I’m assigned to rank 50 Bright Eyes songs next, I will be contacting OSHA or something.
3. Frightened Rabbit “The Modern Leper”
Bad news, my editor just said I can’t expense all the boxes of Puffs Plus or the additional therapy session from doing this list, so the only saving grace here is at least it’s almost done. Another brilliant and dark 2000s song from someone who tragically passed away (in a way that at least one person you knew and loved probably also did) is just cruel and unnecessary. And then another Julien Baker cover decades later, too? Come on. We’ve got plenty to cry about here without that.
2. The Antlers “Epilogue”
To be fair, the anguish of this song — and the entire concept album Hospice — transcends generations. Arguably, this one isn’t even the saddest, depending on which part of the relationship/sickness/death/grief cycle feels most relevant. But for us 30-somethings, we bet you’re going to cry even harder now than in 2009 because you’ve probably lost someone you love in a way that made all these songs feel very different in the years since. Sorry. At least their song “Putting the Dog to Sleep” came out in 2011 and isn’t here.
1. The Flaming Lips “Do You Realize??”
Hold up. How is a song from those psychedelic weirdos perhaps most widely known for performing in giant plastic bubbles, appearing on the SpongeBob soundtrack, and having a band name rumored to be inspired by an STI at the top of this list? Much like the timing of the 2008 recession right when we were supposed to be starting our careers, it sure feels like a cruel joke! But we’ll say it again: Our scientific ranking method doesn’t lie. Pick any lyric in this song, check a heavy, heavy box: mortality, grief, love, contradictory emotions, the vastness of the galaxies, the Earth’s axis. Add in the dreamy swirling chimes and other orchestral flourishes, and we’re crumpled in a sobbing ball under the covers, just like all the other times we heard it in the past 20-plus years. Even all the car commercials somehow couldn’t put a dent in its potency. All right, we’re done. Go call your mom now.
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