Every Fiona Apple album ranked from worst to best

Only a select few artists possess the ability to make audiences feel as though they’re gazing directly into their hearts while they perform. While lyricists may strive to express themselves fully through their songs, there’s often a limit to how much they can reveal before protective barriers start to form. However, Fiona Apple is an exception. Despite only sharing her world with her audience sparingly throughout her career, she has been unflinchingly honest and vulnerable every time she has released an album.

Throughout every era of her career, Apple has made it a habit to take the most beautiful piano ballad and find a way to break your heart casually. Whether that’s talking about the realities surrounding her as a young musician or writing cathartic tunes in the latter half of her career, each of her songs feels like opening a small window to her reality that few can touch.

And while most people have to go to artists like Bob Dylan or this kind of specificity, even Dylan couldn’t boast backing tracks this strong. Being equal parts baroque pop, soft rock, and wild art rock, every piece of Apple’s discography is about breaking new instrumental ground as well as lyrical, which usually means working outside of the piano to create rhythms that sound like controlled chaos half the time.

While there is a definite pecking order for where all of her albums fall, there’s no real use in debating over whether one of them is garbage or not. Apple isn’t one for making terrible albums, and even if they might not be the easiest to listen to all the way through, you’re in for a thrill ride no matter where you land in her back catalogue.

Fiona Apple albums ranked worst to best:

5. Extraordinary Machine (2005)

Any artist will want to put their best foot forward on any album. Even if not everything comes together, it’s better to let the songs speak for themselves rather than worrying if the production isn’t quite up to snuff half the time. But when looking at Extraordinary Machine, Apple deserved better than putting out an album that sounded like it was released kicking and screaming out of the studio.

Because while the songs are great, it feels like Apple is at a distance throughout the entire record. Though she and Jon Brion had something specific in mind for the record, it ended up getting glossed over in favour of newer production names, which leads to the album sounding a little bit dated.

Especially coming after When the Pawn Hits, this feels like a step down production-wise, even if the songs themselves can still stand on their own as beautiful. Then again, the fact that Apple and Brion even bothered to have their version of the album released afterwards is probably the best indication of why the album isn’t as celebrated amongst the biggest names in her catalogue.

4. The Idler Wheel is Wiser (2012)

With all of the label disputes over, Apple felt much more at home going into the next record. She had spent time working with other artists, and by soaking up the wisdom of people like Johnny Cash, it would have been impossible to capture the same energy she had 20 years before. It was time for her to expand, and The Idler Wheel is Wiser is the sound of a singer-songwriter still managing to keep things fresh over the years.

Because outside of the writing, the best aspect of this record is the instrumentation. People had come to expect piano-driven tunes at this point, but bringing in different strange instruments into the mix is what set her apart from the Liz Phairs of the world, especially with percussion that sounds like it’s ripped out of some dirty junkyard.

There are the makings of many good ideas on The Idler Wheel, but the only reason why it’s so low is that it was a harbinger of things to come. A very good proof of concept, but no one was truly ready for the emotional catharsis that would come one album later.

3. When the Pawn Hits… (1999)

It’s every artist’s worst nightmare trying to follow up a blockbuster debut. As much as people may have liked you from the word go, it’s hard to build upon everything when you don’t know why they even liked you in the first place. Despite everyone and their mother having the exact wrong reaction to ‘Criminal’, Apple ran away from her star power and turned in one of the best-sounding records of the 1990s.

The bar was already set high for Tidal, but listening back to some of these mixes, both Apple and Brion created any audiophile’s dream. Although everything about Brion’s work later on the soundtrack to Eternal Sunshine of the Spotless Mind is already here, Apple’s songwriting puts it one notch above everything else.

Across tracks like ‘Paper Bag’ and ‘Fast As You Can’, Apple reminded everyone that she was only beginning to impress us, usually building on the template she set on her first record and writing songs that feel much more lived-in. While When the Pawn Hits isn’t the first album anyone should pick up from her, you’re in for an absolute treat once you have the classics under your belt.

2. Fetch the Bolt Cutters (2020)

Picture this: it’s the beginning of 2020. Everyone is minding their own business when the beginnings of the Covid pandemic start in full force, leaving everyone confined to their homes and trying to make sense of the reality of living with one of the worst diseases of the modern age. Anyone could find themselves trapped inside their own heads after a while, but Fetch the Bolt Cutters was the sound of that feeling gaining sentience.

Throughout Apple’s fifth outing, she turns in some of the most batshit insane music any of her peers could have thought of. Whereas some of the tracks make more sense than others, hearing a kind-of pop song like ‘Shameika’ right next to the Captain Beefheart energy of ‘Relay’ or ‘Ladies’ is one of the most beautifully off-kilter moments anyone can ever have within the span of one album.

Right when it has your attention, though, Apple isn’t afraid to get dark about her past relationships, whether that’s cutting off the cycle of abuse on the title track or making one of the single most disturbing verses the 2020s will ever hear in the final moments of ‘For Her’. Other Apple records could get by through the sheer beauty of the melodies, but if those were the equivalent of acclaimed cinema, this is the disturbing arthouse movie that leaves people with a few scars along the way.

1. Tidal (1996)

When Apple first entered the scene, there was no guidebook for where she could go. Everyone was still knee-deep in the sounds of grunge and alt-rock, and even she was left of centre, she had no interest in catering to the riot-grrrl crowd and picking up a guitar. She got to where she was through pure beauty, and she didn’t bother watering down herself for anyone on her debut.

Whereas most young artists spend their debut twisting their sounds in different directions, everything about Apple’s trademark magic is fully formed before she was even out of her teens. Much like Bjork had done on Debut, this feels like a seasoned veteran in their element, whether that’s making something more tongue-in-cheek like ‘Criminal’, catering to the rock crowd on ‘Sleep To Dream’, or the raw emotional pain behind ‘Never is a Promise’.

Most people are still figuring things out at this stage, but this wasn’t any old debut; it was a warning. The starlets at MTV may have been trying to sell their audiences what they thought they wanted, but Apple was there to deliver the songs that people needed to hear.

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