Fiona Apple (who doesn’t seem to have an official website so here is her Facebook Page, last updated in 2015) is an absurdly talented songwriter/musician/singer who has only released 4 albums in 21 years (and released her most recent one five years ago, though she’s released some interesting things since then). Which she sings, it sounds like she’s been hit with the worst news ever and is using every ounce of strength to keep herself from shattering. She could sing “The Thong Song” and it would sound like a heart-wrenching story about a woman who will never, ever, ever get to see that thong. You’d weep.
I’m going to go out on a limb here and say that every “canon” Apple song is pretty much great which makes ranking her songs (at best) a foolish endeavor. Still, I endeavored foolishly.
I’ve loved Apple since she debuted. However, for a number of years (specifically years that overlapped the release of 1999’s When the Pawn Hits the Conflicts He Thinks like a King What He Knows Throws the Blows When He Goes to the Fight and He’ll Win the Whole Thing ‘fore He Enters the Ring There’s No Body to Batter When Your Mind Is Your Might so When You Go Solo, You Hold Your Own Hand and Remember That Depth Is the Greatest of Heights and If You Know Where You Stand, Then You Know Where to Land and If You Fall It Won’t Matter, Cuz You’ll Know That You’re Right.) I was dating somebody who despised her with the heat of a thousand fuming Courtney Loves. Not that Courtney Love hates Fiona Apple, just that she, you know, hates people from time to time. As a result, I didn’t really resume my interest in her work until 2005’s shorter-titled Extraordinary Machine. As it happens, that means I only missed the one album and I was able to quickly catch up with her catalog. I recommend buying and downloading everything she’s ever released (with one possible exception, see #18).
And we’re off…
18. Pure Imagination
From a 2013 Chipotle Ad. No, Seriously.
I have three cover songs by Apple on this list and two of them are just perfect. This one is, uh, sort of misguided. Its a cover of “Pure Imagination” from Willy Wonka and the Chocolate Factory. I confess, I might be unfairly prejudiced because this was essentially recorded for a Chipotle ad (though both the song and the commercial could stand apart from the campaign) and I think I get the logic of pairing Apple with this song. I suspect somebody heard her version of “Across the Universe” and tried to find another sort of dream-like song for her voice. The thing is, this is a song that benefits from Wilder’s deliberate coldness in the original – it’s a world of pure imagination, but there’s something slightly sinister about it. I mean, people can imagine some pretty scary things. Apple doesn’t do cold. I feel the barely restrained emotion in her voice (which is generally profoundly effective) strips the song of its darker undertones. As a result, the song sounds a little too on the nose. This ism thus, officially the only song sung by Apple that I don’t especially care for.
17. O’ Sailor
From 2005’s Extraordinary Machine, First Single
So anyhow, every song from this point on is pretty great. The parent album of “O’ Sailor” – Extraordinary Machine – has a long and stories history that is partially shrouded in myth. The myth says Apple’s label withheld the record. The truth appears to be that Apple herself withheld it because she was unsatisfied with certain elements of the production. Before the album was finally released, a bunch of the tracks (with the original production) leaked and a “Free Fiona” campaign was launched by her fans to get the label to release the album. Anyhow, as with all of her albums, this one was quite excellent. “O’ Sailor” was the first single and the accompanying video was nominated for a whole bunch of Music Video Production Company Awards. There doesn’t seem to be a website for Music Video Production Company Awards, so we’re just going to have to trust Wikipedia.
16. The First Taste
From 1996’s Tidal, Fourth Single
6 of the 18 songs on the list (1/3) are from Apple’s debut album, Tidal. She was 18 or 19 when the album was released and its a heck of a debut. Indeed, it would be a heck of a record no matter how old she was when it was released. Apple’s songs tend to be about romantic loss or about longing. “The First Taste” falls into the latter category. There’s a man she’s been flirting with and she’s longing for that first kiss that hasn’t yet come – and she’s beginning to doubt that it ever will. There’s some terrific spider imagery at the heart of this song (which reminds me of Joanna Newsom’s fantastic “Have One On Me”) and a recognition that should this love even be consummated Apple expects to be consumed. No love burns as hot as young love.
From 1996’s Tidal, First Single
Another track from Tidal, this was her first ever single and it really set the expectations bar pretty high for Apple. I mean you might not ever be able to again live up to the quality of this single. I’ve ranked it at number 15 which tells you how successful I think she’s been since. I find the lyrics to “Shadowboxer” to lean a little heavily on cliché but, hey, Apple was 18 or so when she wrote it. I’d be proud to write a song as good as this even if it was cliché-laden. This is a song of romantic loss and from the maturity and honesty in Apple’s voice I can only assume there was an 18 or so year old boy out there who really stamped her heart flat.
14. Parting Gift
From 2005’s Extraordinary Machine, Second Single
“Parting Gift” is another bitter break-up song. There’s some speculation online that part of the reason Apple takes so long between records is that she doesn’t make music unless she’s been recently dumped. I don’t know nearly enough about her personal life (I don’t even know if “Apple” is her real last name or indeed if “Fiona” is her real first name – I really should look that up) to make any sort of judgement about this. I tend to believe that she’s just a perfectionist and works hard to shape each song into its ideal form. Anyhow, what I like about “Parting Gift” is the shift up that occurs when she hits the choruses. I also love the metaphor of how her former lover stared at her the way that a dog stares at food. We all should be wanted as honestly as that at least once in our life.
13. Slow Like Honey
From 1996’s Tidal, Second Single
“Slow Like Honey” is a gorgeous, slow burning torch song about longing for somebody who hasn’t quite decided if they’re interested in you yet. Well, that’s how I interpret it. It’s sort of a companion piece to “The First Taste” in that regard. What really sets this song apart from the songs before it is Apple’s vocal performance. The vocal build in intensity and almost burst out of her careful control at the end. There’s an old theatre saying (which I’ve referenced before) about how one should feel 10 but show 7. Apple nails that here.
12. Hot Knife
From 2012’s The Idler Wheel Is Wiser Than the Driver of the Screw and Whipping Cords Will Serve You More Than Ropes Will Ever Do, Music video release
Yes, I am always going to be using the full titles of her two ridiculously long-titled albums. Why do you ask?
I love this song so much. It’s not quite an a capella song theatre features (I think) five vocal tracks – four sung by Apple and one sung by her sister Maude Maggart (ok, I looked it up – Apple is her middle name). The song wasn’t officially released as a single (only one song was and it wasn’t the wonderful “Werewolf” because by 2012 singles weren’t especially a thing as they were in the 20th century) but she did make an outstanding video (directed by her former flame, Paul Thomas Anderson). The lyrics are so simple but are genius. She starts things out suggesting that she’s butter and her (potential?) lover is a hot knife but flips it around halfway through to suggest that she’s now the hot knife and he’s the butter. Apple might write songs about wanting and waning love, but she’s never weak. On first listen, you might miss the other two lyric lines that join in late in the song. Pay extra attention to them if you can – the music becomes wonderfully complex. What a fantastic song.
Many of Apple’s early fans had walked away by the time The Idler Wheel Is Wiser Than the Driver of the Screw and Whipping Cords Will Serve You More Than Ropes Will Ever Do was released. If you’ve not heard it, download it like now.
11. Across the Universe
From the soundtrack to the 1998 Film Pleasantville, First single
Even though I’ve known for years that John Lennon wrote this song, every time I hear it I think “Wait, you mean George didn’t write it?” He didn’t. John did. The Beatles contained multitudes. This is not the first John Lennon song I’ve written about (#73) but it is the first Beatles song to appear on any of my lists. I’ve not yet placed The Beatles in my on-deck circle. Indeed, nor are they “in-the-hole.” In fact, they’re not in my current batting line-up. I’m intimidated to write about Prince and David Bowie because of the depth and breadth of their catalog but I’m intimidated to write about The Beatles because so much has been written about them by so many better writers. I don’t have much to add to the conversation about any of the musicians I’m writing about but, holy cats, you can’t accidentally click a link on the Internet without running into a Beatles song.
That all said, Apple really nails this cover of “Across the Universe.” While I like the Beatles’ musical performance better, I think there’s something about Apple’s voice that bring out a sense of wonder and desire in the song. It sounds like Apple is just now experiencing everything she’s singing about. I’ve often argued that Tom Jones is the best cover singer in my lifetime – virtually every song he chooses to sing he makes better. I think Apple could conceivably be just as good a singer of covers provided she (like Jones) carefully curates her selections. I could listen to her forever.
Coming Soon: The other cover and nine originals