When the world first heard of one Fiona Apple, we really didn’t know just what hit us. The singer-songwriter from New York City is unlike any artist that came before her, and she also is clearly ahead of her time. Apple’s career had much promise in the late 90s, but many argue that the delays in her music production have hurt that promise somehow. Still, Fiona Apple’s appeal is difficult to explain because she’s in a league of her own. All five of her studio albums are landmarks in the industry, and here we’ve ranked them all from good to best.
5. Extraordinary Machine (2005)
It may be difficult to market an artist who’s not driven to be commercially viable, but that’s truly the basic factor that sets Fiona Apple apart from all the other apples in the orchard. Extraordinary Machine was finally released in 2005 after a six-year delay due to some record label-infused fiasco. While her music in Extraordinary Machine had clearly grown up quite a bit from her Tidal days, there were a lot of darker nuances in her lyrics that loom behind the whimsical sound of the entire album. The most popular namesake single is probably the most accessible song here, but there are still layers of rawness idly peering through in some of her phrases. Extraordinary Machine may be the last on this list, but it certainly doesn’t mean it has anything to prove to anyone. Apple did as best as she could under pressured circumstances, and she also managed to somehow stay true to her form.
4. The Idler Wheel is Wiser Than the Driver of the Screw and Whipping Cords Will Serve You More Than Ropes Will Ever Do (2012)
Entirely acoustic and somewhat strange to say the least, The Idler Wheel… is one challenging and fascinating album. It gives us Apple totally unrestricted, and we aren’t yet sure whether that’s the greatest thing or not. The sounds that Apple produced in this album are as haunting as ever, but not many melodies remarkably stand out. You may have to listen to a track repeatedly to get its gist, but you’ll soon find that most of her songs on The Idler Wheel… ages much like fine wine. Apple was destined to create a collection of songs that’s as bare as her lyricism is, and we believe she’s her best when it’s just her—stark as can be on her piano. We hear this unapologetically on Hot Knife, and it’s disarming how powerful Fiona Apple could really be. Ballads like Valentine remind us of a visceral Apple quality that looks a lot like pain but sound more like beauty.
3. Tidal (1996)
Fiona Apple’s debut album sits comfortably in the middle of this list. Although Apple was clearly underdeveloped and still unfocused during this time, this album marked the point when her genius was put on the pedestal. Whether that was good for her career or not is still debatable to this day, but the album did give us some unique and memorable classics. Criminal is angst-driven and full of raw personality—after all, she was still a teenager when the album was released. She showed skill in variety from the touching ballad Never Is a Promise to the playful samba approach of The First Taste. It wasn’t a surprise that the album went platinum after one year, but it also set a high precedent for Apple and her next album. Let’s just say that the multiple Grammy award-winner did not disappoint.
2. Fetch the Bolt Cutters (2020)
Grown up and middle-aged Fiona Apple is very much welcomed and even more refreshing than we ever could imagine. Fetch the Bolt Cutters was released in 2020 and happens to be Apple’s fourth studio album. To say that her sound has come back full circle is an understatement. She sounds like she’s having way too much fun on this album and it’s to everyone’s benefit. The catchy hooks and distinct Apple-esque piano phrases are scattered throughout Fetch the Bolt Cutters. Did Apple succumb to the pressures of commercial success? We believe it’s all just due to maturity and supreme confidence in her sound and her art. We can totally see the direction she’s headed to, and we all want to go along for the ride. It’s no surprise that Fetch the Bolt Cutters won a Grammy for Best Alternative Music Album and the song Shameika also won one for Best Rock Performance. After such a long hiatus, Apple made an unmistakable point with this album and we’re glad she did.
1. When the Pawn… (1999)
At one time, When the Pawn… held the world record for being the longest album title at 444 characters, but that’s the least of Apple’s achievements with this album. When the Pawn… became a huge success commercially, and it’s considered by many to be one of the best albums of all time. The complexity musically was nothing new for Apple, but lyrically, Apple exchanged her youthful explorations to deeper reflections on relationships, sacrifices, and pain. She put her flaws and her soul on the line, and as it turns out many people could relate. This was the first time that we truly got a glimpse of her sense of self with sultry ballads such as Love Ridden and Get Gone. Fast as You Can was the single that only someone with Apple’s talent could ever create. I Know was arguably the highlight of the album—Apple as she was singing about infidelity as if it was the industry that cheated on her. She came out on top as it seems today—proof that strength is abundant among those that go through life the hardest. When the Pawn… is easily the best studio album that Fiona Apple has ever created, but we believe there’s more great things to come from her.