Fiona Apple Songs, genre exploration, and ranking her five studio albums. What are the best Fiona Apple Songs? Check out the Amazon Music Playlist, “Fiona Apple of My Eye” below.
Top Fiona Apple Songs and Albums
Fiona Apple has captivated audiences with her unique voice and deeply emotional songwriting since her debut in 1996. Over the years, she has released five studio albums, each showcasing her talent and artistry. From the hauntingly beautiful hit “Criminal” to the introspective “Every Single Night.”
This article goes over all 5 albums, the best songs, and includes a playlist with my 3 favorite tracks from each record and 4 songs you might not have caught, including a duet with Jurassic Park’s own Jeff Goldblum.
5. Tidal (1996)
Her debut album that made her a star. It features her distinctive voice, complex lyric structure, and heart-wrenching melodies. While this is the record that still, 28 years later, considered her iconic album, it is my least favorite from songwriter but only because I think her music got better as she matured. Only 17 when she recorded “Never is a Promise,” it shows her rawness and offers glimpses of the masterworks that would come along later in her career.
Featured Fiona Apple Songs from debut album Tidal:
“Criminal” – the grammy-winning single that put Fiona Apple on the map and is still probably her most recognizable song amongst the masses. The themes of guilt and redemption are universal and fleshed out beautifully. This song and video gave Apple the success she needed to sustain a bold and unconventional career as one of her generation’s greatest songwriters.
“Slow Like Honey” – by far my favorite track on this CD. It’s jazzy vibe is irresistible, the rich instrumental is classic, and the lyrics are beautiful. “When reality and fantasy lie too far apart…” The dreamy atmosphere shows Apple’s ability to evoke strong emotions. This song is one of m favorite of all time, by any artist.
“The Child is Gone” – This song touches the loss of innocence, the pains of personal growth, and contemplates on the passage of time. This is considered a hidden gem on the album, which unfortunately feels more like a collection of songs than a fully cohesive record. Nonetheless, when she hit it right on Tidal, she hits hit hard, raw, and with grace.
4. When the Pawn Hits...(1999)
Her second album marked a powerful evolution in her music’s sound and lyrical depth. Although it didn’t contain a huge hit like her first release, it separated her as an artist exploring themes that other singers who reached such heights in terms of fame wouldn’t dare touch. Again, this is only ranked as he fourth best because I feel the other three were so much better. This one still feels more like a collection of good songs than a complete album that seamless flows. Here are my three favorites from this one, the full title of which is pretty long.
Featured Fiona Apple Songs from follow-up album When the Pawn Hits…:
“On the Bound” – This track kicks off the album, setting an intense tone with deep piano chords and raw lyrical delivery. I love the explosion of poetry that happens early in the song and then rapidly descends to the beautiful wailing of “You’re all I need…” on repeat. This song demonstrates Apple’s vulnerability, strength, and her ability to confront emotional turmoil with fearless self-awareness.
“Fast as You Can” – The first single of the album, this energetic song blends the genres of jazz, rock, and alternative rock elements. The frenetic piano playing and dynamic vocals creates a delicious sense of urgency. The musical versatility on display here is fantastic. The lyrics suggest hints of addiction, including both the thrills of the high along with the cravings and submission to follow.
“I Know” – This hauntingly captivating ballad contrasts sharply with the album’s more intense segments. The song is a testament to Fiona’s lyrical prowess, featuring a heartfelt exploration of love, acceptance, and regret. Clearly about an act of betrayal or infidelity, it is an honest, chilling expression of love, pain, and resilience. (The iTunes exclusive version is slightly better than the album version but both are great.)
3. Extraordinary Machine (2005)
Six years after her second record, Apple’s third album marks a period of personal growth for the artist. The album is filled with intricate arrangements and poignant lyrics, forming a more cohesive offering. However, there is an evident frustration felt throughout that results in Apple at her most raw – for better and occasionally for the worse. This was my least favorite album for years and then after experiencing a pretty rough patch in my life, a lot of songs I had overlooked hit the spot hard and true. I had always loved the title track, “Better Version of Me,” “Parting Gift,” and “Waltz (Better than Fine)” but it wasn’t until later that I truly appreciated “O Sailor,” “Red Red Red,” and “Oh Well.”
Featured Fiona Apple Songs from debut album Extraordinary Machine:
“Better Version of Me” – This song’s upbeat tempo and whimsical instrumentation combines jazz elements with power lyrical design. Along with the title track, this strong song boasts an emergent voice that is triumphant over life’s adversity. These themes are in tense conflict with the more frustrated and scorned feelings prevalent on other tracks of this record. “The nickel dropped when I was on my way beyond the Rubicon…” It’s so good.
“Parting Gift” – This song can be interpreted as aimed at a lover, an addiction, or simply a habit that the singer used to love, but has outgrown. It exemplifies Fiona’s deeply personal writing style, reflecting on the end of a relationship with bittersweet clarity. This is one of the best songs about the complexity of letting go, moving on, and the lingering emotions that accompany such an act.
“Oh Well” – This raw, emotionally charged song lays bare the immense feelings of resignation. The sparse arrangement highlights her unique vocal talents, with the poetic lyrics taking centerstage. The song’s brutal honesty, presented in stark simplicity, makes it one of the record’s best tracks. This, along with “Red Red Red,” need to be experienced with a similar feeling of loss fresh in the listener’s gut to be fully understood.
2. Fetch the Bolt Cutters (2020)
The title of this one comes from an obscure quote on the TV show Bones, which I just think is quirky and very on-brand for Fiona Apple. This album, along with her fourth release, are the two Apple records that feel like complete works with a comprehensive concept. Staying in a similar musical space that she encroached with The Idler Wheel… This bold experimental journey breaks new ground in her discography. It is a testament to Fiona Apple’s bold creativity, pushing musical boundaries while standing firm in her distinctive vision’s foundation. Shameka, video seen below, is a great song that has a great story attached to it – look it up!
Featured Fiona Apple Songs from debut album Fetch the Bolt Cutters:
“I Want You to Love Me” – this song starts Apple’s first release after an 8-year drought. This track is a raw and powerful declaration of longing and vulnerability that is the most reminiscent of “Extraordinary Machine” than any other song during this last musical outing from Fiona. It has an unconventional structure and captivating lyrics, creating a compelling opening statement.
“For Her” – This song stand out among the other tracks on this stellar album. Clearly inspired by aspects of the “me, too” movement and a certain Supreme Court judge, this is one of the fiercest works churned out by Apple. The cowbell is utilized at a genius level and the screams come from the bottom of the singer’s throat, revealing her terrifying strength as an artist. Dealing with themes of trauma and systemic injustice, this striking arrangement makes it an unforgettable part of the record.
“Drumset” – I am partial to this song over others on the album that are on par with it for a simple reason, I’m a drummer and my drums are not at my house but a friend’s basement. This song felt special to me while it highlights Apple’s skill in using sparse arrangements to convey deep concepts and emotions. Flittering through feelings of loss and disconnection, it makes it a notable addition to the record. It was really hard to pick between this, “Shameka,” for which she won another grammy, the title track, and “Heavy Balloon.”
1. The Idler Wheel... (2012)
Not as long as “When the Pawn Hits…” the title of this one is still a doozy (see below). But this album is in my opinion, by far, Fiona Apple’s best album on the whole. It runs together seamlessly, it stays cohesive and doesn’t get impatient like in earlier albums. Rather than just a collection of songs, this one is her masterpiece with each song playing a vital role in the construction of the record. Not just my favorite record by Fiona, this is one of my Top 5 Albums of All Time.
Featured Fiona Apple Songs from debut album The Idler Wheel is Wiser Than the Screw and Whipping Cords Will Serve You More Than Ropes Will Ever Do:
“Every Single Night” – The opening track sets the tone for this album with deeply personal artsy lyrics played to a hypnotic melody. It captures the internal struggle of overthinking along with emotional turbulence. The vocals along with the minimalist arrangement make it an unforgettable introduction to a breathtaking work of art. The way she sings “brain” is mesmerizing.
“Werewolf” – Realistically, every track on this record deserves a spot as ‘featured’ song but I am restricting myself to three per album so there are definitely some songs I “regret” (wink wink) not including. But nonetheless, werewolf is a wonderful example of her whimsical and poignant storytelling ability. The song cleverly juxtaposes the ferocity of a werewolf with the complex emotions involved in a turbulent relationship. It is a showcase for Fiona’s talent for blending raw emotion with alluring narratives.
“Largo” – The closing track is a perfect sendoff marked by the prevalent themes of longing and self-discovery. This intricate arrangement guides the listener on a drunken stumble to play a live show at “the Largo,” suggesting it better to be “drinking” and “singing” and “stuff” than to stifle one’s creative spirit and succumb to the darkness of the void. It highlights her growth as a musical artist.
Here's a music video I made in 2014, featuring my daughter:
