Late last year, we published a pretty epic list of incredibly tough books for extreme readers. Our readers clearly like a challenge, because it drew heaps of discussion, and as such, we thought we’d extend the challenge to other areas of pop culture. First up: music! Here’s a selection of 50 albums that we think make for particularly challenging or difficult listening, because they’re emotionally harrowing, technically demanding, or just plain old make your ears hurt.

1. Aphex Twin — Drukqs
His Selected Ambient Works, 85-92 is a bona fide classic, and one of the most visionary and important electronic albums — or any other sort of albums, for that matter — of the 1990s. This later release is a whole lot less accessible, but even on first listen, it presents some moments of startling beauty. It does also present plenty of moments where the casual listener might find themselves asking, “What the actual fuck is this?” Stick with it. It makes sense. I promise.

2. Autechre — Confield
You can pick pretty much any of Autechre’s albums here. It’s not that they’re interchangeable — indeed, their career has undergone several distinct periods — but more that they’re all variations on a theme, which is abstract, cerebral, intimidatingly complex electronic music. See also: Squarepusher.

3. Atari Teenage Riot — The Future of War
The future of war, it appeared, involved someone taking a sledgehammer to a Commodore 64 and recording the results. Hey, it’s better than drones and dirty bombs.

4. William Basinski — The Disintegration Loops
It’s not so much difficult as it is immersive and weirdly beautiful — but still, at the end of the day, you’re listening to the same tape loop for an hour.

5. Björk — Drawing Restraint 9
Our Icelandic heroine’s most out-there moment, made as a soundtrack to her husband Matthew Barney’s similarly, um, ambitious film. Björk’s work has occasionally flirted with this level of weirdness — Medulla, in particular, was pretty strange — but this is easily her most “difficult” release, for better or worse.

6. Boris — Flood
Like standing next to a glacier and listening to it inch its way toward sea level. Except amplified about a gazillion times, and played at the other end of an aircraft hangar by four crazy Japanese musicians.

7. John Cale — Music for a New Society
Arguably Cale’s masterpiece, but also his most challenging record, largely due to the air of paranoid despair that surrounds its songs. The album has a particularly distinctive sound, based around weirdly distant production and sparse piano accompaniments. The songs themselves are more like freeform narratives than anything resembling traditional verse/chorus compositions, and their subject matter — as the title might suggest — is pretty much unrelentingly bleak.

8. Can — Tago Mago
Clearly, all of Can’s music is an… interesting listening experience, especially if you’ve not come across it before. Their early work, from when the famously erratic Malcolm Mooney was their lead vocalist, is particularly intense. But the second half of Tago Mago is just batshit crazy.

9. Captain Beefheart — Trout Mask Replica
Perhaps the most famously deranged record in the rock ‘n’ roll canon, and one that’s either going to prove the most amazing thing you’ve ever heard and/or give you a headache. (One doesn’t preclude the other, although in your correspondent’s experience, to be honest, Trout Mask Replica inclines more toward the latter than the former.)

10. Coil — Musick to Play in the Dark, Vol. 1
Are you shivering? Yes. Yes I am.

11. Miles Davis — Bitches Brew
One of those records that keeps cropping up on Greatest Albums of All Time lists, and one whose historical significance can’t be denied — the crazy rhythms, the fusion of rock and jazz sounds, the spirit of unconstrained innovation. But Jesus, have you tried to listen to the damn thing? It’s hard work. Best of luck.

12. Death Grips — No Love Deep Web
An aural experience best approximated as being punched in the head repeatedly by an intimidatingly large man.

13. The Dillinger Escape Plan — Calculating Infinity
When people talk about “math rock,” this is what they’re referring to — music that sounds like someone is trying to work out Fermat’s last theorem on guitar. If it makes your brain hurt, you’re not the only one, but it’s fascinating listening nonetheless.

14. Faust — Faust
The strangest band to come out of the great creative explosion in 1970s Germany, and considering their contemporaries were the likes of Can and Popul Vuh, that’s saying something.

15. Flying Lotus — Cosmogramma
On Twitter yesterday, someone asked Flying Lotus if he likes acid. His response: “Loved. We are taking a break for a while.” And listening to this record, yes, you can definitely see that at one point in his life, FlyLo must have been very fond indeed of psychedelics. Bless.

16. John Frusciante — Smile from the Streets You Hold
From Frusciante’s “dark” period, i.e. the time he spent holed up at his house in the Hollywood Hills, shooting terrifying quantities of heroin and letting all his teeth fall out. There’s a curious, naïve beauty to parts of this album, but by god is it ever pretty harrowing listening.

17. Diamanda Galás — The Litanies of Satan
If there really is a hell, this is probably what Old Nick plays to meet you at the gates.

18. Godspeed You! Black Emperor — F#A#∞
Godspeed’s debut, and perhaps still their most demanding record. It’s like listening to the end of the world, except that instead of some dramatic explosive apocalypse, everything comes to an end in a slow, drawn-out grind. (It works best if you have the vinyl version, because the needle locks into a groove at the end, meaning that, as the title suggests, this album technically lasts forever.)

19. The Knife — Shaking the Habitual
Go on, listen to “Old Dreams Waiting to Be Realized” all the way through. Every time around.

20. Liars — They Were Wrong, So We Drowned
They have settled into something of a groove of late, but Liars’ early albums were as notable for being radically different from one another as they were for being strange and intense listening. This record, in particular, bewildered pretty much everyone when it came out (as sprawling concept albums about witches are wont to do).

21. Lightning Bolt — Hypermagic Mountain
Not quite as intense as the band’s all-action live performances, but still, not the sort of thing you put on for a quiet Sunday morning, either. Not unless you have some hardcore post-party cleaning to get done, anyway.

22. Mansun — Six
They’re remembered these days as Britpop also-rans, which is a shame, because Mansun were one of the weirder and more fascinating bands to come out of the UK in the late ’90s. Their debut album Attack of the Grey Lantern was strange enough, with its tales of stripping vicars and egg-shaped Freds, but it was only warming up for the feast of weirdness that was Six. Featuring narration from Tom Baker of Doctor Who fame (no, really), it was a concept album, I guess, although the concept in question really only made sense to Mansun themselves.

23. The Mars Volta, generally
And speaking of crazy concept albums, here’s your one-stop shop. Drug comas! Bedlam! A weird diary their sound guy found in a car!

24. Melt-Banana — Charlie
Just like having a brain aneurysm, only crunchy.

25. Merzbow, generally
And if lasting through Melt-Banana doesn’t tie your synapses into knots, this should do the trick nicely. Hey, you read this far — you can’t blame me.

26. Micachu — Jewelry
Features a vacuum cleaner being used as an instrument, among other things, which should give you a pretty good idea of what to expect here.

27. Mr. Bungle — Disco Volante
Of all his myriad projects, Mr. Bungle has always been the outlet for Mike Patton’s strangest creative urges. And they don’t get much stranger than an experimental free-for-all named after James Bond’s yacht.

28. My Bloody Valentine — Loveless
It’s a classic, sure, but MBV’s sound takes some getting used to, mainly because they extracted sounds from guitars that no one had really managed before (or since, for that matter).N Once you do, though, you realize there are some pretty wonderful pop songs buried under all the layers of distortion.

29. Neutral Milk Hotel — In the Aeroplane Over the Sea

30. Joanna Newsom — Have One On Me
It’s intimidatingly long, for a start, and Newsom’s, um, distinctive vocals have always been an acquired taste. With an album so sprawling and ambitious, there will always be moments that don’t quite work, but Have One on Me is worth sticking with, because it contains some of Newsom’s best songs, as well as some of her most demanding.

31. of Montreal — Hissing Fauna, Are You the Destroyer?
Kevin Barnes’ masterpiece, and also the album wherein he undergoes a metamorphosis into a black trans woman by the name of Georgie Fruit. A demanding concept, an emotionally wrenching collection of songs, and one particularly lengthy composition that feels like a fever dream (“The Past Is a Grotesque Animal”) — this one’s got it all.

32. Yoko Ono — Between My Head and the Sky
Ono has been given something of a raw deal by history. It doesn’t matter how much weird and wonderful art she makes; to the man on the street she’ll always be the one who broke up the Beatles. But then, y’know, fuck the man on the street, because some of Yoko’s work is just as interesting as anything Lennon and McCartney ever made. This album, in particular, is an underrated gem, featuring Cornelius, Yuka Honda of Cibo Matto, and her son Sean on guitar and multi-instrumental duties.

33. Radiohead — Kid A
If it’s a struggle now, imagine how poor Radiohead fans felt circa 2000, when they discovered that their heroes had spent the three years since OK Computer suffering mental breakdowns and creative crises (and listening to Warp’s back catalog, clearly).

34. Lou Reed — Metal Machine Music
Hey, at least you’re not the publicist who had to try to push this on its release.

35. Shabazz Palaces — Black Up
The most fascinating hip hop release of recent years, and also one of the least approachable. Its oblique sounds and fractured, arrhythmic beats make it a far cry from the simple kick/snare template of conventional hip hop, but it’s worth sticking with, because once it clicks, Black Up makes perfect sense, and is most excellent indeed.

36. Slint — Spiderland
A post-rock touchstone, and a demonstration of just how far rock ‘n’ roll could depart from its conventional structures while still maintaining a guitar/bass/drums template. Spiderland is definitely an acquired taste, and not a record that appeals to everyone, but its influence and ambition alone make it, if nothing else, interesting listening.

37. Elliott Smith — From a Basement on the Hill
Difficult in that it’s one of the most emotionally demanding records you’ll ever hear, especially if you’re familiar with Smith’s story (and who isn’t these days?). Songs like “Kings Crossing” and “Strung Out Again” are particularly hard work given their author’s struggles with drugs, but it’s the quietly heartbreaking “Twilight” that’s this album’s centerpiece, and arguably the best (and most forlorn) song Smith ever wrote.

38. Soft Machine — Third
Space rock! This was apparently inspired by listening to Bitches Brew, which makes perfect sense when you listen to it. Soft Machine were never particularly interested in making conventional rock ‘n’ roll, but this record took their experimentalism to an entirely new level. God only knows what people made of it in 1970.

39. Sun Ra, generally
I mean, we’re talking about a gentleman who was convinced he visited Saturn at some point during the 1930s, an experience that informed both his music and his general world view.

40. Sunn 0))) — Black One
Features, inter alia, vocals from a claustrophobic man locked in a casket, which is about as terrifying to listen to as it must have been for the poor bastard to record.

41. This Heat — Deceit
Falling somewhere between Can and Throbbing Gristle, English late-’70s experimentalists This Heat’s music is an underrated pleasure, so long as your definition of “pleasure” involves someone playing several albums simultaneously while hitting a saucepan with a hammer. It’s fascinating listening, though. And speaking of Throbbing Gristle…

42. Throbbing Gristle — D.o.A: The Third and Final Report of Throbbing Gristle
None of the great English industrial pioneers’ albums are easy listening, but only one of them contains “Hamburger Lady,” perhaps the most flat-out disturbing song ever committed to vinyl. And it’s this one!

43. Scott Walker — Bisch Bosch
At some point during the 1980s, Scott Walker underwent one of the strangest career transformations in 20th-century music: from largely forgotten ’60s crooner to waaaaaay-out-there experimental maverick. His albums since have only gotten stranger and stranger, and you could really choose any of Tilt, The Drift, or Bisch Bosch here — but only the latter contains a seven-and-a-half-minute ballad about Nicolae Ceaucescu. And fart noises.

44. Tom Waits — Swordfishtrombones
And while we’re talking about weird transformations, what about Tom Wait? He went from down-at-heel barroom balladeer to… this?

45. White Noise – An Electric Storm
Experimental electronic music from the 1960s! I’ve written about this album a fair bit before on Flavorwire, so suffice it to say that it involves sampled orgasm sounds, a soundtrack to “a black mass in hell,” and contributions from Delia Derbyshire of Doctor Who theme fame. It still sounds remarkable, nearly half a century after its release.

46. Whitehouse, generally
Whitehouse have long concerned themselves with making “extreme electronic music,” and they do it oh so well. This makes the likes of Atari Teenage Riot sound like slap-happy chart pop, and that’s before you even get to the lyrics, which concern fun topics like rape and child abuse. Hilariously, they’re named after British “morality campaigner” Mary Whitehouse.

47. Xiu Xiu — Knife Play
Music just wouldn’t be the same without Jamie Stewart. And if you think his songs are deranged, you should see his Twitter account.

48. Frank Zappa — Shut Up and Play Yer Guitar
You’ll never be able to play it quite like this, though.

49. John Zorn — Kristallnacht
The title suggests that you’re not in for a fun listen, and sure enough, Kristallnacht is Zorn’s most challenging and discomfiting work (and that’s saying something.) “Never Again,” in particular, with its unrelenting soundtrack of breaking glass, is pretty difficult listening, but also deeply moving and thought-provoking.

50. And finally… free jazz, generally
I haven’t written a great deal about jazz here because it’s not really my field of expertise, but honestly, if you can get into free jazz, you’re a braver person than I am. Godspeed.

(Source: http://flavorwire.com/434857/50-incredibly-tough-albums-for-extreme-listeners)

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