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51 Indie Songs From the 2000s Ranked by How Much They Can Still Make Millennials Cry

Ah, the 2000s. A simpler time, when a thousand weird mp3 blogs all named “Melted Acetate Owl” or something were a thing. Climate change and American politics were only, like, regular-bad. Indie music had it all: Sweaty danceable post-punk. Earnest folksy acoustic fare. Quirky eclectic pop. Garage rock revival and the revival of the revival. Emo-adjacent rock. Sadness galore in all genres!

Well, dust off your first-generation iPod and draw the curtains in your pathetic little apartment. It took us an unprecedented 114 crying interruptions, two breakups, and eight failed attempts to log back into our LiveJournals, but we did it. We’ve scientifically ranked 51 both extremely popular and lesser-known indie songs of the era based on how much they can still make you sob.

Also, we can already hear you yelling in the comments about what “indie” technically is or isn’t, and we’d appreciate it if you’d spare our aging ears and fragile hearts. This is a very big tent here, okay?

51. Air “Highschool Lover”

Let’s start out easy — this one doesn’t even have any lyrics! Except wait, the music itself is a little nostalgic and melancholy, and oof, it’s from the “Virgin Suicides” soundtrack. I don’t want to do these rankings anymore already.

50. Doves “Caught By The River”

All the instrumental hallmarks of the era’s big stirring britpop, but the lyrics just feel broadly emotional rather than outright sad. Rating: Mascara still intact.

49. Grizzly Bear “Two Weeks”

Okay, not inherently super depressing. More like “a routine malaise” — get it? This mega-hit was inescapable in every coffeehouse and other artsy space in 2009. Now your local artsy space is long gone and replaced by, depending on your location, either a Dollar General or soulless “luxury” apartments.

48. Cat Power “He War”

Ranked low on this list because we’re FINALLY over our college exes (mostly) and not punching walls while playing it on the Discman, but it’s still an iconic powerhouse of a song.

47. The Mountain Goats “No Children”

Everyone knows this one. The TikTok teens know this one. It’s made the rounds so much that even though it’s still pretty dark, it’s also kinda funny and it ultimately doesn’t hurt much (Julien Baker live cover notwithstanding, obviously).

46. The Walkmen “The Rat”

Nice when this classic rocker pops up on Spotify while you’re trying to “get your steps in” on a clunky mini-stepper on your living room carpet on a Saturday night. All your friends have kids and don’t even text you on your birthday. The line “Now I go out alone if I go out at all” feels pretty real now.

45. Keane “Everybody’s Changing”

From the poppier segment of the the Sad Soaring British Rock era. Still pretty but just moderately sad. Even though, yes, everybody is still changing and I still don’t feel the same.

44. MGMT “Time To Pretend”

Even when the beats were party-ready enough to shimmy around in your metallic American Apparel A-line skirt and the band’s persona was carefree and ironic, the lyrics were often still bleak. At the time you heard this song and thought the future corporate drone life described sounded bad. Turns out … it’s all bad.

43. Animal Collective “My Girls”

Back in 2009, this was a pleasant and possibly realistic vision: “With a little girl and by my spouse/I only want a proper house.” Now, have you seen Zillow and Tinder lately? Both are a nightmare, delete the apps from your phone right now.

42. Yeah Yeah Yeahs “Maps”

Another banger that you can dance to while magically still getting upset. The deep longing! The lyric repetition! The fact their biggest payday came from Beyonce sampling the song. What a world.

41. The Knife “Heartbeats”

Has there ever been a more emotional song about … a one-night stand? Didn’t think so. That’s the music era we’re dealing with here, folks. Bonus: Listen to the delicate José González cover, too, and cry in a more acoustic sort of way.

40. Of Montreal “Wraith Pinned to the Mist and Other Games”

Singing over a bouncy bassline about pretending you don’t exist and pretending you’re in Antarctica was mostly just good ol’ kooky fun back then. Now as the climate fully collapses, it’s more of a dire warning.

39. Cursive “The Recluse”

Seriously? Another song about a one-night stand that winds up hitting unexpectedly hard? Whether that’s still your life these days or you’ve been faithfully married forever, it’s time to feel things again with that spider metaphor.

38. Iron & Wine “Such Great Heights”

What an uplifting and spirited rendition of an already upbeat song. Listen to this beautiful acoustic cover while remembering that “Garden State” is almost 20 years old now. That’s old. But not in a cool retro way. In a cringy outdated way. Just like you.

37. VHS or Beta “Burn It All Down”

More of that extremely 2000s danceable bleakness. Little did we even know back in college how much more we’d want to burn it all down now.

36. Built to Spill “Liar”

“It takes up all your life/these decisions you make” was so deep and philosophical in your LiveJournal bio. Now the decisions are, like, whether to email or Slack your boss a polite request to finally take one vacation day and maybe which violent Netflix show to zone out to before not sleeping.

35. The Decemberists “Sons & Daughters”

Do you have kids by now? Do you not have kids? All right, good for you either way, but just wait until the harmonies in the refrain about the bombs. Oof.

34. Bon Iver “Skinny Love”

Is it a classic? Sure. Is it still sad? You bet. We’re going to rank it lower just because you’ve probably heard it enough times to build up some emotional immunity. I think that’s a thing. I also really don’t want to listen for the 7,000th time right now.

33. The Good Life “Album Of The Year”

The excruciatingly detailed tale of a failed relationship. No matter how many times you hear it, you’ll desperately hope that maybe this time, things will work out for the poor guy in the song. And also for you. (No such luck for either.)

32. Shout Out Louds “Wish I Was Dead Pt. 2”

We’re getting deeper into the list now, the tears are flowing, and there’s something just a little too comforting about those “were featured on ‘The OC’ soundtracks and are morbid but not in a metal way at all” sorts of songs.

31. The Postal Service “The District Sleeps Alone Tonight”

We’re dancing! But we’re sad! Here we go again with perhaps one of the best-known bands to perfect this devastating combo in the 2000s. You know this song. You probably also know The Postal Service is hitting the road on a 20th anniversary tour this year, and you may have even bought tickets while fretting about how your creaky back will cope and whether or not your credit card can handle the cost.

30. Interpol “Slow Hands”

If you still don’t know exactly what this excellent gloomy song is about, a commenter on a lyric discussion site posted, “Get off the internet all the time and maybe you won’t be sad” as the interpretation. In 2004. Maybe they were on to something, guys. Let’s try it.

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