You could argue that there are only two kinds of songs: those about love and those about the loss of it. Anyone who’s ever made a heartbreak-inspired mixtape or walked straight from last encounter with a lover to the nearest dive bar with a jukebox can tell you which kinds of songs are more soulful, soothing, and transporting. No offense to love songs—there are many great love songs—but it's the lonely ones.
Loneliness and silence certainly have terrific chemistry, but for me, loneliness and music are the better pairing. Great songs have made the most soul-crushingly lonely moments of my life bearable. The train ride in France when I realized my high school crush, a girl on my foreign exchange trip sitting just a few seats away, would go unrequited. (A friend slipped headphones over my ears and hit play on Bruce Springsteen’s Greetings From Asbury Park, NJ. I’d always hated The Boss; I’ve loved him ever since.) The breakup phone call from a young single mother I knew I shouldn’t be dating but was having too much fun to stop. (The relationship had started with all sorts of late-night debauchery, morphed into a few semi-serious months, and ended courtesy of AT&T. I sulked in my apartment and then blasted Radiohead’s "Everything In Its Right Place" defiantly.) Whatever the romantic tragedy, I could always find a simpatico singer to share in my misery or an agitated frontman to express my grief.
Lyrics are the most obvious ways to find solace in music, but as much as I love Hank Williams, when I’m so lonesome I could cry, I don’t want to hear him yodeling those words. I’d rather put on Pink Floyd’s "Wot’s…Uh the Deal" from Obscured By Clouds (yes, over the more obvious "Comfortably Numb"), adding a floater of hopefulness to the mix. "Let me in from the cold/Turn my lead into gold/Cause there’s a chill wind blowing in my soul/And I think I’m growing old." That is the ultimate pithy chorus about wanting to escape loneliness.
"Music was my refuge," said the great Maya Angelou. "I could crawl into the space between the notes and curl my back to loneliness."
Ironically, some of us also like to secretly revel in those times in our lives when we find ourselves forlorn. We want to sink into loneliness, awful as it seems. We want it to last.
Jeff Tweedy perfectly captures this paradox in "How to Fight Loneliness," one of Wilco’s most popular songs. On the surface, his advice to “smile all the time” sounds like a plausible suggestion for how to combat loneliness, a variation on “Don’t Worry, Be Happy.” The shuffling melody perhaps supports this, but the atonal piano, backwards guitar, and downcast delivery suggest otherwise. Tweedy continues to sing, in his soothing, perhaps medicated voice, “shine your teeth ‘til meaningless/and sharpen them with lies.” The smile, it turns out, is a ruse; Tweedy is pretending that everything’s A-OK, but it’s not. He’s lost this fight.
I spent a long time on the ropes after a breakup from a woman with whom I’d spent the better part of a decade, a woman who had seemed to be my soulmate but who had other ideas, listening to a sickeningly slowed down cover of “Six Months in a Leaky Boat.” Renamed “Six Mile in a Leaky Boat” for some reason by a band brilliantly called Winechuggers, the lyrics registered like a call to keep sinking, to submit to becoming a true outsider—someone immune to love and skeptical of relationships. “Shipwrecked love can be cruel/Don’t be fooled by her kind/There’s a wind in my sails/To protect and prevail.” The original, by the wholly underrated New Zealand band Split Enz, is a peppy new wave number that could never be construed as a downer song. That version’s joyous crescendo wouldn’t be out of place in a Broadway musical, even. But the singer of Winechuggers recognized the plaintive tone in the lyrics and turned it into a dirge.
Some of the songs mentioned here appear on this playlist I’ve made The Lonely Hour, even though, in a few cases, they triggered memories of moments spent alone that I’d prefer to forget. I’ve added some lesser-known tracks by cult artists like American Music Club (“I’ve Been a Mess”), some recent tunes that bring a fresher perspective like Courtney Barnett’s “An Illustration of Loneliness” and while I’ve left out great jazz, soul, and R&B laments over loneliness, it makes for a good soundtrack to a lonely night. (Be warned, though: It does skew heavily white-dude hopeless romantic, I’m afraid.)
Loneliness can be a maddening descent into insecurity, that place that makes you feel like something’s wrong with you and no one will ever love you. It’s hard to escape. In the end, you either trick yourself into coming out on the other side, smiling, or you go deeper, getting lost for a while, and you change. Either way, you emerge with a new favorite song.