29. Kings of Convenience “Homesick”
The Norwegian Simon & Garfunkel that brought you the cute hit “I’d Rather Dance With You” also invites you to quietly revisit your early-adulthood philosophical crisis. “Homesick, ‘cause I no longer know where home is.” I mean, this would hurt less if “home” were a house you owned, but we all know that worked out for us.
28. LCD Soundsytem “New York I Love You But You’re Bringing Me Down”
We will allow you to slide this one up or down a little in the rankings based on your proximity to New York and your relationship with it. But the way the details ring even truer now is pretty upsetting no matter where you live.
27. The Shins “Caring Is Creepy”
That’s right, more “Garden State” soundtrack material! You know the “one day I’ll be wondering how I got so old” line? One day is here now, folks. And you still have three roommates and no dental insurance. At least the song holds up.
26. Sondre Lerche “Side Two”
On an otherwise mostly jaunty-to-effervescent indie pop album, this slightly dissonant dirge is always there to ruin our day. By the way, we’re the “tortured old” now, not the “tortured young.” Bye!
25. fun. “The Gambler”
This song will still ruin you if you, my millennial friend, also have Boomer parents who got divorced and will not be living out the tender story “The Gambler” tells. In fact, you may have started sobbing when you first heard it sung live. Hypothetically.
24. Hem “Half Acre”
If you prefer your weepiness in a delicate orchestral indie folk form, you’ll love this chance to reflect on all your regrets. “Do you carry every sadness with you?” At least the ending is hopeful — if you can make it through without trying to charge up your 2007 Motorola Razr2 to read old texts from your ex.
23. Arcade Fire “Sprawl II (Mountains Beyond Mountains)”
What’s sadder than the song you used to angstfully blast while driving past the “dead shopping malls” on the way home from your pathetic suburban job? That same song, but now you’re old and still at those jobs and now the band’s singer also has been accused of sexual assault. Cool, cool.
22. M. Ward “Chinese Translation”
Here we go again with the “deceptively catchy.” Just because you can sing along — and I’m pretty sure people even clapped along to this one at a show — that doesn’t mean it’s not a trigger for your 23,480th full-on existential crisis. Like hangovers, they’re much worse at this age now, too.
21. Feist “Let It Die”
Let’s go, it’s time to tear into the old wounds of your worst early 20s breakups. Remember, “The saddest part of a broken heart isn’t the ending so much as the start.” Open up those old Facebook albums you made private a while ago and really dig in!