In the Aeroplane Over the Sea – Neutral Milk Hotel (1998)

In the Aeroplane Over the Sea - Neutral Milk Hotel (1998)

Has this remarkable outsider vibe, despite being one of the most acclaimed albums in history. An assortment of surrealism, idiosyncrasy, sorrow, pain, and beauty. Goddamn, is it beautiful… not in a conventional way at all, but listening to Jeff Mangum pour his heart out accompanied by marching bands, freaky organs, and musical saws is a fantastic, engrossing experience. The title track turns madness into stately beauty, sounding like a eulogy to someone who never actually existed but would’ve been your best friend if they had. And good luck not getting swept up in the bizarre emotions of Oh Comely, emotions I’m not even sure they have names for. Genius or insanity? I say both!

Choice Cut: In the Aeroplane Over the Sea

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Mule Variations – Tom Waits (1999)

Mule Variations - Tom Waits (1999)

Tom Waits has maintained a huge cult following since the ’70s despite never having had a hit, simply because he’s written a gigantic pile of great songs over the past forty years. And if you’re not part of the Tom Waits thing yet, here’s as good of a place as any to get on board. Those who want to hear his insane side will find it on What’s He Building? and Filipino Box Spring Hog, and those who are more into Tom as the jazzy singer-songwriter putting out his cigarette in the ashtray on top of the piano and taking a deep swig of whiskey will love Picture in a Frame.

Choice Cut: Come on Up to the House
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Bone Machine – Tom Waits (1992)

Bone Machine- Tom Waits (1992)

Tom Waits follows up his legendary ’80s trilogy with his twisted, demented vision of blues rock. Earth Died Screaming, In the Colosseum, and Goin’ Out West (which you might remember from Fight Club) not only reinvent the tired genre – it’s turned into the soundtrack to the apocalypse. Even the gospel song Jesus Gonna Be Here sounds like it came out of hell. We also get three of his greatest ballads, Who Are You, A Little Rain, and Whistle Down the Wind, as well the unclassifiable, undeniably moving I Don’t Wanna Grow Up. Tom at his most striking, most violent, and most tender.

Choice Cut: Whistle Down the Wind
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The Wild Hunt – The Tallest Man on Earth (2010)

The Wild Hunt - The Tallest Man on Earth (2010)

Kristian Matsson’s music is proof that they do indeed make ’em like they used to. Shit, in some ways, maybe even better. The Bob Dylan/Nick Drake comparisons are obvious, but you get a far wider variety of emotions packed into each song, and he makes you feel them on a much deeper level than I’ve ever got off of either. Even from the first time I listened to this, I felt some weird kind of longing and nostalgia. It makes me think of times gone by, people I’ve known, life, love, death, the past, present and the future.

Choice Cut: King of Spain
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