1. I See A Darkness (1999)

On the album’s first track, Oldham sings of fading into oblivion as maggots rest on his arm, and that’s about as sunny as I See a Darkness gets. It’s a Gothic meditation on death and depression and the most direct artistic statement Oldham has ever made.

But if it’s so dark (which, make no mistake, it is) why do I feel uplifted by it? Maybe it’s because while the specter of our own demise hangs over the entire record, Oldham is able to recognize the absurdity in it all. After listening to songs like “Death to Everyone,” it doesn’t make much sense to fear something so inevitable. And yet it might make even less sense to not fear it. Then there’s all the anachronistic language and bizarre imagery ; biting monkeys, poking urchins, and arm maggots are just a few of the creature comforts that inhabit this world. But while you’d expect these tricks to put distance between Oldham and the listener, it actually brings us closer to the subject matter. Like all great works of gothic art, the imagery gives us a less terrifying vocabulary to talk about what terrifies us most.

Of course it’s easy for Oldham and me, hopefully decades away from death, to laugh in its face. (If you really want to feel the full impact of the title track, behold Johnny Cash’s Devastating Cover released three years before his death.) It helps too that Oldham deals with these issues by going beyond the sexual encounters and empty church hymns that gave him false solace in the past, looking instead to friends and true lovers.

At the end of “A Minor Place,” Oldham sings, “I thank the world it will anoint me if I show it how I hold it.” His prediction turned out to be right. With its ability to switch effortlessly from gut-wrenching melodrama to black comedy, I See a Darkness stands alongside The Seventh Seal and Synecdoche, New York as one of the best works of art about death ever created.