Top Ten Songs by Fiona Apple

With her first hit single at 18, Fiona Apple took MTV and the music world by storm. The depth and maturity of her self-composed songs impressed critics and fans alike. Each album reflects her deepening wisdom and self-analysis, and each individual song is like reading a page from her diary. All are intimate, making you feel as if you are living inside Fiona Apple’s mind. Below is a list of ten of her best songs from three albums.

1. Criminal

No list of Fiona Apple hits would be quite complete without a nod to “Criminal”, her first hit single. It’s an edgy tune about a girl who just can’t help using men. You’re not quite sure if her desire for forgiveness is sincere or if she’s being tongue-and-cheek, but it’s a fascinating song. You can find this Grammy-winning song on Fiona’s first album, Tidal.

2. Sleep to Dream

This Fiona Apple song is the first track on the Tidal album. It has strong drum beats and focuses on a girl who is fed up with being misled by her lover. She says she “doesn’t go to sleep to dream”; she is grounded in reality even though her lover is unrealistic and hiding emotionally.

3. Pale September

A touching song full of medieval references, it is a hidden treasure on the Tidal album. “Pale September” is an exquisite ballad about letting go of internal barriers and finding true intimacy with the one that you love.

4. Love Ridden

Another touching ballad, this Fiona Apple song is about breaking up rather than coming together. It’s a song that reflects divorce and the tenderness that is part of loving someone yet not being able to be close to them anymore because it’s just too painful. The lyrics are fabulous and you’ll find yourself singing it over and over again. It’s one of the most vivid songs in Fiona’s collection because you can see the entire ballad as a movie in your head. This song appears on her sophomore album, When The PawnâÂ?¦ (The title is a paragraph long so I am abbreviating it)

5. Extraordinary Machine

The Extraordinary Machine album went through some shifts and changes and some tracks were redone or let go of. However, this song survived the revisions of the album and is a testament to Fiona’s indestructible nature. On her official site, Fiona Apple says that this song represents how she feels about herself. It’s about being resilient and able to move through the ups and downs of life no matter what.

6. Tymps (The Sick in the Head Song)

From the newest Fiona Apple album, Extraordinary Machine, this song is about seeing an ex-lover and doing something foolish-like kissing him! It’s a self-evaluative song about whether she is really falling back into a pointless cycle with a relationship that can’t go anywhere or whether she’s just acting out of the memory of having loved someone deeply. It’s one of the more upbeat and catchy songs of the album.

7. Parting Gift

This is the first release from the Extraordinary Machine album. It’s a song about not listening to intuition about a relationship that really isn’t good for you. Fiona Apple remembers the beauty of how the relationship started but laments not listening to the signs earlier. It’s a tender song of reflection.

8. Fast as You Can

This was a hit from When the PawnâÂ?¦ which showed a significant break from Fiona’s Tidal album. “Fast As You Can” is just like its name implies: it’s a fast song with words jumbled together in interesting creations. Fiona admits that she’s more crazy than her boyfriend can handle and that if he knows what’s good for him, he’ll just push her away before she gets in too deeply under his skin.

9. The Way Things Are

In this song, Fiona Apple realizes that she can’t change and that she’s just better off leaving things the way they are. She wants to make up with a loved one, but she can’t even fathom of how to do that, so she agrees to just keep going as is, no matter what people say about her. This medium-tempo tune appears on When the PawnâÂ?¦

10. Shadowboxer

Another hit from Tidal, “Shadowboxer” is about being seduced and discarded, yet still feeling affected by your former lover. Fiona sings that she will become a “shadow-boxer” so that she won’t be seduced by the charm of her ex-lover ever again.

Bonus- 11. Paper Bag

It was hard for me to condense this down to ten Fiona Apple songs, so here is a bonus entry! This song is about having a deep hunger for someone but not being able to get the love that you really need. Fiona worries that her emotional issues are pushing her lover away even as she accepts that he’s immature.

Fiona has a unique way of combining music to lyrics. The first album was a smooth integration of piano, drums and lyrics and each album after that lost some of the traditional form as Fiona explored her own way of blending words to music. She has said on her official site that she wants each song to be it’s “own little world” that listeners can get lost in. Each time I loose myself in one of her songs, I find little pieces of myself coming back to me that I didn’t even know were gone.