“Play Crack the Sky” by Brand New - The dark, brooding final track of 2003’s Deja Entendu that had me weeping in my emo hoodie over my breakup with my high school boyfriend.
“In the Aeroplane Over the Sea” by Neutral Milk Hotel - Really, any song from their 1998 album would do, so we’ll just go with the title track. “Some day we will die, and our ashes will fly from an aeroplane over the sea. But for now we are young, let us lay in the sun, and count every beautiful thing we can see.” Indeed, Jeff Mangum, indeed.
“Jet Black New Year” by Thursday - Always a bridesmaid, never a bride. This song never made it on to an album, just their 2002 “Five Stories Falling” EP, but be careful if you listen to it while driving because I’ve found myself caught up in the relentless final crescendo (that doubles as an ultra-clever countdown to midnight) going well in excess of the speed limit.
“California Love” by Tupac Shakur featuring Dr. Dre - one of the greatest rap songs ever recorded and the song that introduced me to hip-hop. I vividly remember sitting in my bedroom in my parents’ house in 1996, trying to clandestinely tune in to V103 on my little radio in hopes that I might hear it and feel like I was part of the West Coast party, too.
“A Perfect Sonnet” by Bright Eyes - My favorite song of all time, period. Released on 1999’s Every Day and Every Night EP, Conor Oberst’s tortured, straining vocals make the song swirl and rumble over a frenetic backing track. I’m honestly not even sure what it’s about, but it’s captivating.
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