Ten Brilliant Albums That Take Multiple Listens To Understand

Many of the best pop records of all time will click instantly. Michael Jackson's Thriller, Madonna's Like A Prayer and The Beach Boys Pet Sounds are full of buttery smooth songwriting that is easy to understand and delicious on the ears, and they all deserve the acclaim they collect. These next ten records relish in their difficulty and craft compositions and concepts that push the boundaries for music and as a result, can be tough on their first listens. These albums may be jarring and confusing at first but sticking with them will provide some of the most rewarding musical experiences of all time.


10. Xiu Xiu - Forget (2017)

Xiu Xiu have a long history of making music that can turn your average listener away, but Forget is not only one of their best records, but one of their hardest to fully engage with. Frontman Jamie Stewart can turn from whispering devilishly into your ear to screaming his brains out from a distant and if his erratic but brilliant performances weren't enough pinning them down into a genre can also be very tough. As the band bounces between new age goth, baroque and post-rock elements the pacing can often be dizzy, but as a cohesive experience the album shines.



9. Prurient - Rainbow Mirror (2017)

Prurient is an artist that can be tough to get into no matter what record you try but Rainbow Mirror is another level of difficult. Rainbow Mirror dabbles in pseudo drone style ambient compositions that capture lightning in a bottle and spread that momentum over incredibly long compositions, but that may be hard to fully grasp your first time around as the album is just over 3 hours and 20 minutes long. That is a lot of ambient time and makes it difficult to pay attention to the way they fold in and out of each other creating a final product but once you're able to step back and look at the whole thing, what is here is excellent. 



8. Animal Collective - Spirit They're Gone, Spirit They've Vanished (2000)

If you tuned into Animal Collective in 2009 when they dropped Merriweather Post Pavilion and never dove into the back catalog you may be surprised to see them here, but in the early days of the group Avey Tare and Panda Bear were dabbling in some incredibly experimental sounds. While is is technically a folk album long passages of blaring instrumentals recorded in a very low-fi style give it a harsh edge that won't remind you of Bob Dylan. Through harsh and grating instrumentals, strange vocal manipulations and difficult to follow song structures make Spirit both a tough series of songs to capture, but a very rewarding one. 


7. Earth - Earth 2 (1993)

Earth 2 is here representing most of the Drone genre. Compared to conventional ideas of music this ambient counterpart can just be so much to try and take in at once. Earth 2 is a brilliant trilogy of songs that span the entirety of drone as a compositonal experience, nearly start to finish it is layered with multiple fuzzed out guitars so blurred together it is so easy to lose yourself in the scope of it all. But once you've wandered through the record a time or two you can go in and really understand what the band is aiming for and once you understand one of the best and most difficult pieces a genre has, the rest will be easy as pie. 


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6. Captain Beefheart & His Magical Band - Trout Mask Replica (1969)

Trout Mask Replica is the father of the mentality that is ingrained in every album on this list. Captain Beefheart expressed his musical prowess by breaking all the rules and doing so in a way nobody to this day has been able to replicate. Trout Mask is the sound of calculated chaos, polyrhythmic compositions show instruments flowing in and out of each other seemingly randomly, but when you look at the whole picture everything is calculated that the nuances can be hard to see. It's a very grating listen that even gives many critics trouble but breaking through to see the genius behind the Mask, per say, is crucial to understanding one of the most essential pieces of experimental music ever. 


5. Sun Kil Moon - As Common As Light And Love Are Red Valleys Of Blood (2017)

Singer-Songwriter music can be very indulgent as many indie fans know, but nothing has ever quite eclipsed the indulgence of the third act in the career of Mark Kozelek. Common As Light is an absolute tour de force of simple but textured instrumentation weaving in, out and around long and personal tales told by Mark on this record. Pushing over two hours and with none of its 16 tracks clocking it under five minutes Mark is basically in the world of spoken word, and in that regard Common may be one of the most compelling audio-books you'll ever hear. As Mark connects the dots in his life and keeps his observations on America witty and timely listening along may be a tough ask for those less experienced with musical minimalism. But giving Mark a chance to woo you with his twisting and turning stories and diatribes is a fulfilling and captivating thing, once you realize just how good what he brings on this album is, you'll be happy to discover that there is much, much more.

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4. Joanna Newsom - The Milk Eyed Mender (2004)

There isn't a Joanna Newsom album that you can show to a radio grade music listener that they will enjoy the first time around. But if Ys pulled from elements of classical compositon and then tuned them into brilliant performances, The Milk Eyed Mender was writing its own textbook from the very beginning. The shorter tracks actually make this project a tougher listen to get a grasp on as the rises and falls of the tracks can sometimes happen in swells so quick that you don't even know what to be paying attention to anymore. And on top of this I will say the thing that makes myself and many other huge Joanna fans angry, her voice is very eccentric and can be an acquired taste, while she is a talented vocalist and a brilliant player getting used to all the elements on their own can be a challenge, but then putting them all together is another step entirely. 

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3. Matmos - A Chance To Cut Is A Chance to Cure (2001)

Matmos has a long history of pushing the envelope with creative concepts and interesting tactics to add detail, texture and experience to the electronic music they create. The bands critical moment came in 2001 with the brilliant concept album A Chance To Cut Is A Chance To Cure. The album is an electronic tribute to surgery chopped and screwed from sounds pulled from a surgical theater. From the rough and grating shrills of buzzsaws to the odd and detailed sounds of organs, skin and fat from a far beyond comfortable distance. The sounds are well detailed but its the mixing of them that is so brilliant, moments of explosive sounds are met by comfortable softness in a way that never lets you off your toes. Song after song they blend sounds that can be so unnatural for electronic music perfectly into their works for one of the most interesting projects ever to qualify for the genre.

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2. William Basinski - The Disintegration Loops (2002)

William Basinski's Disintegration Loops can be a touchy listen but it may be one of the most emotionally compelling pieces of ambient music ever recorded. First released in 2002 and then receiving excellent sequels over the next two years the albums are long, indulgent and detailed, the perfect storm for a difficult listen to think of as a whole experience. William had the brilliant idea to take prerecorded ambient tapes that had begun their decomposition and loop through them over and over again, capturing a small amount of deterioration each time. The result of this experiment is the overwhelming and compelling feeling of losing control. As the tapes become longer, less composed and less contained it mimics the feeling of your senses slowly disappearing as life slips away from you. Setting out after the task is a very difficult ask, but sitting down to listen to any of these in one sitting can be a brilliant experience, just don't be surprised if the whole thing doesn't click in one go. 


1. cLOUDDEAD - cLOUDDEAD (2001)

cLOUDDEAD is the album I had in mind when I set out to write this list in the first place. It's a compilation of 6 singles with A and B sides that the trio released throughout the late 90s into the 2000s. The project can be so hard to pin down because it exists within the realm of hip hop, but is so comfortably completely breaking all of its core rules. Using cloudy often ambient backing and abstract song structures cLOUDDEAD is rap in its most avant-garde, but so crucial to so many artists that experiment within the genre. Acts like Death Grips, Danny Brown and Clipping all seem comfortable in the face of one of the most difficult to fully understand hip hop albums of all time. Everything that makes hip hop great is here, textured and detailed instrumentals, brilliant lyricism and killer flows, but each is distorted just enough by its unique compositions and performance to make it a very difficult project for people to put completely together and judge as a full product. But once you give yourself to cLOUDDEAD, it will give back to you one of the most unique experiences hip hop has to offer and one of the most unique and influential rap albums of all time.

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