Review #444: Extraordinary Machine, Fiona Apple

Karla Clifton
3 min readOct 14, 2023

#444: Extraordinary Machine, Fiona Apple

I love an album with an annoyingly complicated backstory.

Let’s just dive in. Fiona Apple’s buddy Jon Brion (who previously produced her record When The Pawn… as well as Kanye West’s Late Registration) needed her to make this record. That’s what he said to the New York Times in 2003, after a breakup he begged her, “Please, please make another album. … I need work that can save me.’’

Well, I’m not sure if the record saved Brion or not, but it certainly had its fair share of problems. Like the fact that the record was set for release in 2003, then delayed and delayed and delayed, with no explanation from Sony subsidiary Epic Records or Apple. Her fans rioted, picketing Sony. Eventually the whole, unfinished cut album was straight up leaked by a random Seattle radio DJ. The record was abandoned, and then, miraculously, in 2006, officially released, sounding entirely different than the bootlegs.

What happened? Two new producers entered the chat, Mike Elizondo and Brian Kehew, Jon Brion’s roommate. And according to this interview with (seriously!), Epic wasn’t entirely to blame for Extraordinary’s failure to launch. He said that both Brion and Apple were frustrated with their inability to get the songs quite right, saying there was “no clear direction” and “a lack of clarity between all of them on how to do it, and I think the label heard it and said they weren’t fond of it.”

Even more interestingly, Kehew said that the leaked album was “definitely not the record that Jon Brion made with her. … Somebody added parts to those things at home — a fan did it or something.” Um, what!! So of course I had to listen to this Frankenrecord, which is handily available on YouTube. The official cut just sounds more like a Fiona Apple record, but I kind of loved the stringy messiness of the bootleg. Though on an individual song level, I preferred the newer one almost every time, with the old one’s peppier version of “Get Him Back” being the exception. Whereas Most Improved Song Award goes to “Not About Love,” which goes from a sketchy, cello-y demo to a short theater piece, starring Zach Galifianakis and featuring Questlove.

Despite the trials and tribulations of its release, I think that this is the most optimistic Fiona Apple record. “Extraordinary Machine” is about resilience, “Better Version Of Me” is self-explanatory, and “Waltz (Better Than Fine)” is what she’s called a pep-talk to herself. It’s an effective pep-talk, at least if you’re writing an album review: If you don’t have a point to make/ Don’t sweat it.

That’s just one of the many simple couplets Apple declaims that sounds like it might be a Biblical proverb. This album that made me realize that she isn’t really a musician, she’s a bard. See songs like “Window,” about how impossible it is to see through even the clearest barrier, and “Please Please Please,” about how impossible it is to create anything original. She doesn’t just write timeless songs about rotten love (“O’ Sailor,” “Parting Gift,” “Red Red Red”), though those ones are consistently great. My favorite line delivery was on the most rotten love song of all, “Oh Well”: What you did to me/ Made me see myself/ Something awful.

Anyway. I maintain that Fiona Apple had the best COVID album, Fetch the Bolt Cutters, and think that record should have made the cut.

Cleverest Song Title: “Tymps (The Sick in the Head Song).” Because of the timpani!

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