I thought it would be easier to choose ten songs I’d never recommend, but to be honest it’s far more challenging than picking my favorites. The list of terrible songs is endless, so what criteria does one use? Terrible songs by great artists? Terrible but popular songs by terrible artists…

First Day of My Life—Bright Eyes This is the first day of my life Swear I was born right in the doorway I went out in the rain, suddenly everything changed Best of 2005, the first in what is now a series of 17 playlists. It was peak ‘oughts,’ an era that my fellow 365’ers consider…

Change — Big Thief I read a few years ago that the vast majority of us stop discovering new music after we turn 30. …

You Don’t Know How It Feels — Tom Petty I’d consider myself somewhat of an expert on break-up concept albums — Damien Rice’s O, The Cure’s Disintegration, Joni’s Blue anyone? All on repeat for life. But there’s one that stands out for me, based mostly upon the context in which it sits in my life. First semester freshman year…

Christmas in Hollis—Run-D.M.C. All attitude aside, I do love Christmas, and nostalgia is my eggnog. My family didn’t have a lot when I was growing up, but my parents saved money all year to ensure a special morning. The Lego set, a Barbie Dream House (for my sister, sorta), a Big Wheel, baseball…

Christmas in Prison—John Prine This is the second COVID Christmas, and the second year without John Prine, who died of COVID early in the pandemic. “Christmas in Prison” is a love song! No, it’s a Christmas song! No no, it’s a melancholic song about unrequited love! …

Anemone — The Brian Jonestown Massacre Anemone is a song about heartbreak, about those angry and desperate days following a one-sided breakup. To those who call it “heroin music,” like Chef David Chang, perhaps they’re right. Even though I’ve skipped that drug, I’ve always been drawn to heroin-addled artists: Lou Reed, most famously. …

Christmas Card from a Hooker in Minneapolis—Tom Waits Listen, it’s time for some real talk. Christmas is a dark ass day for a lot of people, and that darkness is buried under twinkly lights, jingling bells, and fake plastic trees. …

Everybody Knows—Leonard Cohen I saw Leonard Cohen at Red Rocks on June 4th, 2011, just under three months from his 75th birthday. His voice was shakier, but still vintage Cohen. He swayed across the stage for four hours in front of a rain-soaked crowd. FOUR HOURS. I don’t recall what I expected going…