Favorite 2000s Albums: #9 – Fiona Apple – “Extraordinary Machine”

Listen to the official version on Spotify

I’ve always felt a weird connection to Fiona Apple and her music, even though it never really feels like it was intended for me. Mostly because I think she’s misunderstood — as an artist and as a person — due to various incidents and media portrayals. Apple broke through at age 19 with her album Tidal and was instantly thrust into the public spotlight. The results were some unflattering, extremely public moments — namely her controversial music video for hit single “Criminal”, which showed her parading around in nearly no clothing while looking potentially anorexic, and her infamous “this world is bullshit” speech delivered at the MTV Video Music awards after winning for Best New Artist. Along with some on-stage meltdowns, those moments have colored most of the public’s perception of Apple, who is often seen as a poster-girl for pretentiousness and flakiness.

I had the same preconceptions about her before I seriously listened to a note of her music. I knew the name from the “Criminal” video and I knew some of the songs off Tidal. I assumed, like many others, that not only was she an annoying person, but that her music was also bland. In my mind, I had associated her with that Lilith Fair/coffeehouse style of music that is an over-serious woman playing on a piano while reciting crappy poetry and quoting Maya Angelou.

I still sort of feel that way about Tidal, but she released that album when she was 19. 19! I don’t even remember anything I did when I was 19, but it certainly wasn’t noteworthy and I definitely wouldn’t want the world judging me by it. Meanwhile, Fiona’s music matured from there, and her 1999 album When the Pawn… (which has a 90 word title that seems to consciously stick it to people that labeled her as pretentious) is when her music really clicked for me. It was the complete opposite of what I had often imagined her music being: it was creative, it had tempo changes and often eschewed typical pop verse-chorus structure, and it had some arrangements that really surprised me. On top of that, Apple continued to have that jazzy contralto voice and her lyrics are very smart and insightful with clever rhyming. Definitely not crappy poetry. Predictably, the album sold about 1/3 of the copies that Tidal did.

Fiona’s career and reputation faced another challenge after that, as Extraordinary Machine became one of the more memorable fiascoes of the decade. After recording for the album with Jon Brion (who produced When the Pawn…), Apple was reportedly unhappy with the results, which led to the album being shelved. The tracks eventually leaked online, and the infamous bootleg led to an online campaign called “Free Fiona” that sought to get the album an official release. Eventually Apple enlisted Mike Elizondo to re-record the tracks and Extraordinary Machine was finally released in 2005.

The official version gets inevitably compared to the bootleg version, and I personally enjoy some of the takes by each producer. If nothing else, the bootleg is a fascinating glimpse into the role a producer plays and it’s interesting to see what Fiona disliked about the original version. For the most part, her voice shines through more on the official release, while it’s sometimes buried under the excessively ornate instrumentation of the bootleg.

Regardless of which version you listen to, Fiona’s songs are intact, and they’re arguably the best of her career. They cover the same thematic territory that she usually does — primarily relationships and self-reflection — but her lyrics are wittier and more incisive than before. Musically the album feels like a throwback that doesn’t really belong in this decade, with the sounds of early musicals and more oddball baroque instrumentation sometimes joining Apple on her piano. Nothing on the album comes all that close to the traditional radio-friendly piano pop on Tidal.

There are many highlights on Extraordinary Machine, particularly “O’Sailor”, which gets weakened a bit on the official release compared to the bootleg version that has a slower tempo and a minute more length to create its dreamy atmosphere. “Red Red Red” was overproduced on the bootleg but becomes one of the official album’s finer moments thanks to more subtle strings and a more reflective, down-tempo mood. Part of the fun with the album is comparing and mixing and matching the two versions (I eventually created a playlist of the ideal version using my favorite cut of each song).

Extraordinary Machine is a quirky, individual album that captures Fiona’s strengths as an artist extremely well. It feels very detached from any other albums I’ve heard from the decade and I give Apple a lot of credit for following her own artistic muse and forsaking commercial success that probably could have come easy to her after Tidal. Despite all the hoopla around the album’s release and the artist, Extraordinary Machine proves that she’s genuine as an artist and also possesses a phenomenal combination of voice, lyrical abiity, and imagination. This is where many music writers would call her an “extraordinary machine”, but I’m not going to do that because I have too much integrity.

What I think really draws people to Fiona Apple and has allowed her to create a fervent following is that all of her songs seem to be deeply meaningful to her and are sung with great conviction. Her pattern of releasing music seems to confirm this: with three albums (and soon a fourth) in 16 years, she isn’t one to just churn something out to make money. I think the fact that she takes her art seriously is sometimes confused for pretentiousness. Extraordinary Machine was her only album from this decade, and its long awaited follow-up, with its Fiona-y title “The Idler Wheel is wiser than the Driver of the Screw, and Whipping Cords will serve you more than Ropes will ever do” will finally arrive in June.

Author: joshe24

I'm a wannabe writer aspiring to be an aspiring writer.

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