The first song I heard by Sun Kil Moon was “I Know It’s Pathetic But That Was the Greatest Night of My Life.” It’s fitting that this was my introduction to Sun Kil Moon (the moniker of  San Francisco-based singer-songwriter Mark Kozelek), since the song captures something essential about Kozelek’s approach to music. “I Know It’s Pathetic But That Was the Greatest Night of My Life” is sung in modulated, rambling monologues crowded with detail, and the lyrics radiate a self-aware strain of vulnerability. All this, plus jazz riffs, delicate guitar work and an objectively lovely baritone voice. I was obsessed.

“I Know It’s Pathetic But That Was the Greatest Night of My Life” is about a woman Kozelek met after a show in Moscow; she was a missed connection, a lover he didn’t get a chance to love. “Later that summer I picked up my mail / She sent me a letter with a touching detail,” he sings. “I used up my minutes calling hotels / To find you that night but to no avail / I know it’s pathetic, she continued to write / But that was the greatest night of my life.” The delivery of the last line implies this might also have been the greatest night of Kozelek’s life, and the odd smattering of details he shares creates a barren but specific rendering of the moment. “Her name was Cayenne, so young and soft / Her hands trembled badly, her eyes trailed off / To bottles and objects around the room / My backup guitar, a tray of food.”

This is where he leaves us: some years ago, somewhere in Moscow, with a girl named Cayenne who neither he nor the audience will ever really know. Kozelek is always painfully aware of the enormity of what he’s trying to do as an artist, which is to explain not just a mood but his mood, not just a life but his life. Kozelek trades on specificity, which prevents the listener from relating through personal experience. Rather, the song asks for something requiring more work: that we might all try to remember a night that seems extraordinary in retrospect given the ordinariness of our current situation, or that we recall a person who represented something larger than themselves. The song wants us to reminisce freely about the things we cannot forget. It wants to remind us of our capacity for expanding to greet the promise of largesse.

This is a lot to ask, but Kozelek has made a career on the assumption that listeners are willing to engage deeply with music that doesn’t map neatly onto their own lives. His hypothesis often collides with a reoccuring theme: women Kozelek did not know very well, but who became subject matter because something about their existence engaged his imagination. This is difficult territory for any artist, because it raises questions about the ethics of mining material from other people’s lives — particularly when tragedy is involved, which it often is in Kozelek’s music.

In “Carissa,” a nearly seven-minute ode to his second cousin, Kozelek explains her life and death in a mixture of generalizations and detail. “Carissa was 35 / You don’t just raise two kids and take out your trash and die,” he sings, and it’s as heartbreaking as you’d expect. “She was my second cousin / I didn’t know her well at all but it don’t mean that I wasn’t / Meant to find some poetry / To make some sense of this, to find a deeper meaning / In this senseless tragedy. O Carissa / I’ll sing your name across every sea.”

Kozelek is singing about the shocking death of a relative he didn’t know very well, which is risky in the sense that it might seem at first like he’s capitalizing on the intensity of emotions engendered by premature death. “The last time I saw you, you were 15 and pregnant / and running wild,” he sings. Beyond the basic facts, Carissa’s life is mostly conjecture. But isn’t this what we all do, with everyone and especially with people we know only a little? We extrapolate; we imagine what it would be like to inhabit their life. And if they die — especially if they die young, in a tragic accident — the whole enterprise takes on a new urgency.

Kozelek is fascinated by women, and many of his songs are driven by their varied effects on his life. His lovers, his mother, his girlfriends, his relatives: Kozelek acknowledges his own subjectivity when he sings about these women, and in doing so he also concedes the necessary relationship between art and exploitation. Kozelek is culpable and also capable; it’s a joy and a surprise to hear the tender frankness with which he sings about the women who have inspired and razed and tended to his inner life. He sees these women incompletely, but he doesn’t claim to do otherwise.

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