19. Sings Greatest Palace Music (2004)

I'm not entirely sure what the point of Sings Greatest Palace Music is. In lieu of a Greatest Hits album, Oldham rerecorded a selection of songs from his lo-fi 1993-1997 Palace Music days, adding higher production values and more instruments. Some of the songs work -- "Riding" benefits from the addition of vocal harmonies and eerie Western movie strings. And I dig the honky-tonk version of "I Am a Cinematographer" a little. I mean, how many honky-tonk songs are there about cinematography?

But other tracks, particularly those off of "Viva Last Blues," which only the most pop-obsessed production snobs would call "lo-fi," lose their authenticity when ground through this weird Nashville hit-maker machine, where slide guitar and fiddle are added arbitrarily for no other reason than maybe those were the session musicians that showed up that day?

It all reminds me of the Gus Van Sant remake of Psycho, where the words and angles are the same, but it's in color and stars Vince Vaughn. Replace Vince Vaughn with Tim McGraw and you've got a good idea of why Sings Greatest Palace Music is the least essential album on this list.

18. The Brave and the Bold (w/ Tortoise) (2006)

Considering that the three lowest-ranked albums on this list include two collections of covers and a reworking of old hits, I think it's safe to say that Will Oldham is a much better songwriter than arranger. Here he partners with experimental rockers Tortoise on interpretations of Bruce Springsteen, the Minutemen, Devo, Elton John and others. And by "interpretations" this often means "adding a bunch of noise and calling it a day."

There's nothing wrong with noising up some classic songs. Yo La Tengo's “Little Honda" is a perfect example. But in that case, YLT preserved and even enhanced the best thing the original track had to offer, which was its gleeful, youthful energy and inertia. The same can't be said for Oldham and Tortoise's cover of Elton John's "Daniel" for instance, which is turned into a drony, repetitive soup of feedback and barely-intelligible vocals. Many of the tracks are so far-removed from their source material that it begs the question: Why didn't Oldham and Tortoise just write all new songs? They wouldn't be much more enjoyable, but at least they wouldn’t be entirely pointless.

The one exception is Springsteen's "Thunder Road." Oldham and Tortoise keep the lyrics and structure but throw out the rest, reworking the legendary Born to Run opener into a minor key dirge that bears little musical resemblance to the original. It's so unique that you'll barely think about the original, which is about the best metric there is for evaluating a good cover.

17. What the Brothers Sang (w/ Dawn McCarthy) (2013)

For Oldham's most recent album, he and his The Letting Go collaborator Dawn McCarthy crack open the Great American Songbook, covering 13 Everly Brothers songs. So do these old standards tell us anything about the 21st century? The oohs and aahs of "Milk Train" are certainly timeless, though I'm not sure what the world gains from "Somebody Help Me," a song written in 1966 covered here as a 1980's cock rock jam.

For an artist who's at his best exploring the fringes of American folk traditions, a cover of standards doesn't exactly play to Oldham's strengths. That said, he and McCarthy are obviously talented performers. And by sticking largely to the script, What the Brothers Sang is a vast improvement over Oldham's last collection of covers, The Brave and the Bold. However, in a discography that spans 19 albums, you can probably leave this one at home.

16. Arise, Therefore (1996)

After the effortless alt-country masterpiece, Viva Last Blues, Oldham retreated into the shadows once again (neither his name nor any of his aliases appear on this album sleeve). On Arise, Therefore, he’s armed with an incongruous drum machine, a fresh batch of lyrics that could be charitably described as "esoteric erotica," and no intentions to please his growing fan-base. Far be it from me to accuse an album of lacking confidence when it includes a song called "You Have Cum in Your Hair and Your Dick Is Hanging Out." But Oldham's wavering voice, perhaps meant to sound vulnerable, simply sounds unsure of itself. Few would call him a traditionally great singer, but like Morrissey and David Byrne before him, Oldham's vocal strength lies in his unwavering faith in own voice and its stylistic tics.

The album isn't without highlights like the hypnotic title track and the deceptively sunny closer, "The Weaker Soldier." But between the reluctant vocals and the cheesy drum machine, it sounds less like the work of one of the most significant voices of the past two decades and more like your blacked-out uncle bought a karaoke machine.

15. Days in the Wake (1994)

Oldham has said he doesn’t have Christian beliefs, but his relationship to religion is anything but simple. Within 7 minutes of "Days in the Wake," Oldham sings "God is the answer" 9 times. Maybe it's less about piety and more about a need to share his guilt (over sex? Over everything?) with someone who will listen.

For his second album, he’s still firmly stuck in the murk, as the listener's invited to make sense of Oldham's stream-of-consciousness lyrics, as vague here as ever before or since. The narrator kills a dog. Or maybe he is a dog? No, he's a horse. But he's making sounds like a sheep. On Days in the Wake, Oldham's poetics are just as obscure as on his debut, but they lack the strong sensory evocations that made that album such a memorable piece of Appalachian folk art.

But there is one positive change between Oldham's debut and his sophomore release: The guitar-playing. The amateurish chord mashing of There is No-One is traded in for intricate finger-picking and progressions that make Oldham sound like Elliott Smith had he split Portland for Kentucky, but kept the tape-hiss.

14. Master And Everyone (2003)

Will Oldham's career is a perpetual balancing act with stark lo-fi on one side and multi-layered full-band productions on the other. For 2003's Master and Everyone, the scales tipped to lo-fi for the first time since 1996's Arise Therefore. But despite the lower production values, Master is one of Oldham's most easily-digestible albums. What it is not, however, is one of his most memorable. Eschewing both the traditional storytelling of Ease Down The Road and the stream-of-consciousness sound and fury of his early work, Oldham opts for the easy-going repeated phrases of gospel music on songs like "Maundering," "The Way," and "Joy and Jubilee."

The songs are all very nice-sounding, and all the melodies and harmonies fit together as cleanly as Lego bricks, but I'm not sure there's a single guitar riff here that hasn't been played a thousand times before. Sure, simplicity has its own charms, but only if it makes you feel something. And sadly, Master and Everyone is as unambitious emotionally as it is musically.

13. The Wonder Show of the World (2010)

If you're wondering why Oldham goes full-bro on songs like "The Sounds Are Always Begging" (I can just picture him, rail-thin and shaggy bearded, playing it for a girl in his dorm room) it's probably because he didn't write the music, only the lyrics. Emmett Kelly of the Cairo King supplies the chords for Oldham's warbling words. Sure, the music’s a little generic, but it’s also catchy and sweet. And besides, despite the somewhat predictable chord progressions, Oldham's lyrics are as complex and cunning as ever. Opener "Troublesome Houses" is an endearing ode to the wrong side of the tracks, "With Cornstalks or Among Them" takes on the alluring oblivion of rural life, and the Bookends-esque closer "Kids" is a fine entry in the "Will Oldham barely resists despairing about death" micro-genre.

But while The Wonder Show of the World is a solid record, it often sounds as if Will Oldham is little more than a guest on Kelly's album. That's okay, but it would be a whole lot more enjoyable if it were the other way around.

12. The Marble Downs (w / Trembling Bells) (2012)

If Lie Down in the Light is the album most representative of the qualities we associate with Will Oldham, then get ready for the opposite of that. On The Marble Downs, Oldham partners with the Scottish psychedelic rockers Trembling Bells for a big, lush, kitchen-sink epic that recalls the indie rock symphonies of Sufjan Stevens. Admittedly, it's a little weird to hear Oldham sing over harpsichords and her majesty's horn section. There are even time signature changes, which I'm pretty sure are outlawed in Appalachia.

Sure, some on the songs go on a bit long, collapsing under the weight of the band's instrumental indulgences. But tracks like "I Made a Date (WIth an Open Vein)" and "Ain't Nothing Wrong With a Little Longing" are among the catchiest things Oldham has ever been involved with. It makes me wonder about the career Oldham would have had if he'd grown up in Scotland, drinking whatever they put in the water that makes Belle and Sebastian and Frightened Rabbit write such infectious songs. All the while, Oldham sounds as comfortable on technicolor Scottish moors as he does in the Kentucky lowlands. If listeners are less comfortable with it, well, that's their problem.

11. Wolfroy Goes to Town (2011)

Usually when musicians take a stab at a particular style then fail to achieve greatness, they either abandon that line of attack or keep going down the same road until nothing but oblivion awaits them (see Weezer). But Oldham has never let critics guide his artistic journey. And like on the excellent Beware, when he returned to the Nashville sound that failed him on Sings Greatest Music, here Oldham returns to the quiet, earthy, simplicity of his 2003 misstep Master and Everyone -- but with radically-improved results.

The stand-up bass and subtle orchestral flourishes bring Van Morrison's bucolic Astral Weeks to mind. But these are no loose, languid love songs. Sussing out a central theme of the lyrics isn't easy, but Oldham is clearly concerned with notions of power and oppression as on "New Whaling" where he sings of the "awful actions" of a king amid swirling call-and-response vocal harmonies. On the somber "There Will Be Spring," creatures "run in fear from you and me." It's hard to tell if he's singing about regimes or relationships, but Oldham is clearly made uncomfortable by his strength, singing "Nothing is better, nothing is best" on "We Are Unhappy," his most direct expression of existential grief since "I See a Darkness." Wolfroy Goes to Tow, like so much of Oldham's work, has a tendency to lull the listener into complacency with its beauty. But on repeated listens, the record's dark heart bubbles to the surface.

10. There Is No-One What Will Take Care Of You (1993)

The biggest shock about hearing Oldham’s debut album for the first time is his vocal performance -- rough and reliant on his Appalachian holler to stand out. But lyrically, he arrives fully formed, especially on "Long Before" where he evokes God and sex and death amid an ancient American South that feels somehow older than America itself. Here, as on later albums, the songs are less about character and narrative and more about sensations: The smells and sounds of often very unpleasant things, like William Faulkner with nylon strings.

But just when the darkness and obscurity seems too much to take, Oldham breaks into the gripping bar-room confessional "(I Was Drunk At The) Pulpit" which, while dark, is told with the focus and clarity of an alcoholic who knows he's had enough, but prefers the dirty drunken singing of ale-houses to the cold, perfunctory psalms of the church house. Even 20 years after its release, it remains one of Oldham's most powerful songs.

9. Superwolf (w/ Matt Sweeney) (2005)

Even though only a couple of these songs have drums, Superwolf is the closest thing Will Oldham has to an arena rock album. With the help of Chavez guitarist Matt Sweeney, Superwolf takes some of Oldham's most intimate and darkest lyrics and renders them in widescreen. As a result, the album's complex themes of sexuality and abandonment are magnified instead of getting lost in the hugeness of it all (more Terence Malick than Michael Bay).

On songs like "My Home Is The Sea," Sweeney's classic rock-inspired riffage is a welcome companion to Oldham's folk poetry, resulting in the best album late-era Neil Young never made. Sweeney also knows when you hold back as on "Beast For Thee" where the gorgeous music acts as a counterpart to Oldham's softly savage lyrics. But the best is saved for the gripping penultimate track, "Blood Embrace," which charts the dissolution of a relationship gutted by jealousy and insecurity.

Compared to the disastrous Sings Greatest Palace Music, where too much instrumentation killed any chance for intimacy and authenticity, Superwolf strikes the perfect balance, projecting the contents of Oldham’s brain onto a grand canvas.

8. The Letting Go (2006)

When Oldham recorded The Letting Go he was a long way from Appalachia: Iceland, to be exact. Is it obvious? The production is certainly more crisp than your average Will Oldham release, with immaculate vocal harmonies instead of mountain yelps, violins instead of fiddles (there is a difference). Whether that comes off as cold or beautiful or both is up to the listener. Some of the string arrangements do little more than create manufactured drama, like we saw with so many post-Britpop bands around that time.

But a good melody is a good melody no matter how hard you hit it with a glockenspiel mallet, and while longtime fans of the "punk from Kentucky" might not take kindly to Oldham having gone "full Godrich" (the producer was actually Valgeir Sigurðsson, but who can tell) few would argue with the level of songwriting sophistication Oldham had achieved at this point in his career . From the tale of conflicted lovers on "Lay and Love" to the snowbound affair of the title track, The Letting Go is a powerful album about facing cold truths about the ones we love.

7. Wai Notes (w/ Dawn McCarthy) (2007)

The only things that turn me off about the otherwise-great The Letting Go are the over-produced orchestral flourishes that create little more than faux-drama. Thank goodness then for Wai Note, a collection of demos recorded prior to The Letting Go which strips down those songs into raw, intense no-fi gems. It's Oldham's least-produced album since the Palace Music days, but as evidenced by The Letting Go, his songwriting and vocal abilities have vastly improved since those early records. The result is the best of both worlds: Deeply intimate performances (that could almost pass for early 20th century recordings) coupled with some of the best songs of Oldham's career.

In addition to wonderful tracks that didn't make it onto The Letting Go like the wild backwoods madness of "Signifying Wolf," many of these recordings are as good or better than the ones that made the cut, including a particularly raw and beautiful version of "I Called You Back." You don't need a 30 piece orchestra to create something grand and gorgeous, at least not if you're Will Oldham.

6. Joya (1997)

From the crunching chords and tense piano that kick off Joya’s opening track, it's clear that Oldham’s found his confidence again after the misstep, Arise, Therefore. (Boom, boom, the drum machine is dead). On songs like the lost friendship tragedy, "Antagonism," Oldham possesses a newfound control in his vocal performance, able to sound ashamed without sounding ashamed of his own voice. He also begins to make peace with the darkness inside himself, a theme he would fully explore to great ends on his next album, I See a Darkness, singing, "Why keep awful thoughts and feelings inside of thee / Why not mete them out ever so generously?"

Sex is another thing Oldham is able to consider with more levity than before. It's still a cosmic head-trip for him, but at least he's able to laugh about it as on "Rider." (Spoiler: Oldham's grandpa-beard is the thing being rode).

In a review of its bleaker predecessor Arise, Therefore, Drowned in Sound's Aaron Lavery writes that because of the stark production and uncompromising attitude, "There’s no hiding from these dark tales and the characters that inhabit them." That’s true, but at his best Oldham is more than a mere dispatcher of depressing stories. And I prefer my Oldham with a sense of humor like the one exhibited on Joya; not to soften the blows of his sad observations, but because it helps paint a more complete picture of the human experience.

5. Beware (2009)

In an interview with Uncut, Oldham said he was in awe of the session musicians brought in to rework old songs for Sings Greatest Palace Music. But for my money, they've got nothing on the group of players on Beware, Oldham's first full-fledged country album of new material. Maybe it’s because the songs on "Beware" were written with the "Nashville sound" in mind, but either way it vindicated Oldham's country music chops in the minds of fans who thought Sings Greatest Palace Music was basically an unmitigated disaster.

That said, the album doesn't really kick into high year until the fourth-track, "Death Final," a stately mandolin jam that finds hope amid pits of bodies and angels of death. Other highlights include the hilarious and derangedly catchy fiddle tune, "You Don't Love Me" which if nothing else will etch the image of Oldham's stomach jiggling onto your brain, and the Southern prom slow dance, "I Don't Belong To Anyone." It all leads back to one conclusion: Somebody needs to get Oldham a guest-spot on Nashville opposite Coach Taylor’s wife. Let’s start a petition. We can do this, people.

4. Lie Down In The Light (2008)

If you charted every Will Oldham album on a quadrant, with the Y axis representing "lo fi" and "hi fi" and the X axis representing "country" and "rock," then "Lie Down in the Light" would sit right in the middle. It may not be as grand and Gothic as I See A Darkness or as perfectly-crafted as Viva Last Blues, but in many ways it's the consummate Will Oldham album, bringing together every disparate strand of poetry and pop music that has shaped his career.

From the porch-swing folk of opener "Easy Does It" to the church organ waltz "I'll Be Glad," Lie Down in the Light guides listeners through over a hundred years of Southern music traditions including Kentucky bluegrass, Appalachian folk, and New Orleans jazz. As always, what brings it all together is Oldham's strange senses of humor, romance and dread that permeate every song. Lie Down in the Light sounded like swan song for how perfectly it summarized his career, but we all knew better: Oldham will almost surely keep making albums as long as his hands and vocal chords will let him.

3. Ease Down the Road (2001)

Is that a guitar solo? A guitar solo on a Will Oldham album? And I don't mean a wail of anguished skronk but a real slab of Steely Dan wonkery. When this noodling surfaces on the first track, "May It Always Be," it announces a side of Oldham we haven't seen before. And it's not just the crisp production courtesy of indie rock journeyman David Pajo that shocks. Here, Oldham embraces the no-bullshit storytelling approach of his alt-country peers like Wilco and Whiskeytown.

Following the dark, timeless poetry of I See a Darkness, Ease Down The Road is a bit of a come-down. But in the context of late 90s/early 00s alternative country, it's one of the best albums that era had to offer. The bouncy road-trip of a title track finds warmth, beauty, and humor in marital infidelity (only "a little guilt, and some guilt spilt"). And "After I Made Love To You," a personal favorite of Oldham, is as sweet and honest a love song as you're likely to hear anywhere.

2. Viva Last Blues (1995)

Has there ever been a greater leap forward in such a short period of time than the one between Days in the Wake and Oldham's third album and first masterpiece, Viva Last Blues? Even the Beatles needed Help! to get from Beatles for Sale to Rubber Soul. On Viva, Oldham teams with Steve Albini, who had just completed recording Nirvana’s In Utero, one of the most polarizing albums of all time. Unlike that album, where Albini indulged in and encouraged Cobain's most brutish, noisy tendencies, here the producer achieves a clean, bright, yet never overly-polished sound that finally allows Oldham's songwriting to blossom. It's not all that different from what Albini achieved on the Pixies’ Surfer Rosa, injecting white noise between each instrument and voice to highlight the care put into these compositions, without sacrificing a shred of authenticity.

And as if he was afraid of being drowned out by all the new instruments, Oldham's vocal performance is a revelation, particularly on the opener "More Brother Rides" where his voice is loud and snarling yet technically impeccable. Someone forgot to tell him that vibrato is supposed to be beautiful.

Throughout Viva Last Blues, Oldham's ever-strange lyricism is only complimented by the music's accessibility, particularly on the weird sexual conquests of "The Mountain Low" and "Work Hard / Play Hard." All Viva's missing is an overarching historical theme and it could've easily become as iconic and important to the modern hipster as "In the Aeroplane Over the Sea."

Viva Last Blues also features the best song Oldham's ever written, "New Partner." Here all of his signatures are on display, from the wild naturalism to the crippling guilt, yet it's all anchored to an ascertainable narrative about lost love and one hell of a melody. It may lack the epic sprawl and transcendental concerns of some of his other work (including the #1 album) but Oldham never made a record so inviting and easy to love.

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.