This month saw the 20th anniversary of Fiona Apple’s When the Pawn…, a uniquely masterful album whose title also uniquely doubles as a second-year MFA prose poem. This anniversary ushers us into November, a time of transition, a time when the sun for many of us begins setting at 4 pm and our thoughts turn to the darker, more dramatic angels of our nature. It’s a time when seasonal depression settles upon many of us, often as a downy supplemental layer on top of our Original Flavor depression. Into this fray enters Fiona Apple’s discography, ready to accompany whatever individual journey of harrowing self-interrogation and reflection you’re on today.

A note about the selection here. Some covers are included; some are not; there is no real organization system determining why, other than whether or not I care about them. She has a lot of covers. Features on other artists’ songs are not included. If I have forgotten something, I will gladly add it at its correct place on this list.

EDIT: Now including 13 new hot hot tracks from Fetch the Bolt Cutters!

70. “Hot Knife”
This is Fiona Apple’s version of Countdown and it’s such a delight every time. No existential despair! Just a hot knife. Hot Knife/Butter 2020.
69. “Anything We Want”
This is such a dead-on, sexy evocation of when you and somebody else are first crazy about each other and are doing insane things like trying to psychically communicate to each other in a CVS at 2 am while buying condoms and chewing gum where you want them to kiss you when you get home. It’s only sad IF listened to in tandem with Not About Love, which, whew.
68. “Better Version of Me”
There’s something so comforting, I think, about the self-awareness and forward motion of this – “I’m a frightened, fickle person/Ooh mister, wait until you see what I’m going to be.” It embraces self-knowledge but rejects self-deprecation and keeps it moving. Inspiring! Fiona Apple is a Virgo.
67. “Heavy Balloon”
This is so intense to listen to but feels like one of her most joyful songs to me? Also a cousin in some ways to Better Version — the refrain is about the insistence and irrepressibility of growth, of moving forward. A very good song to bellow the chorus to in the backseat of a car crossing a bridge at night with your friends.
66. “So Sleepy”
This song is truly bananas as I believe it was written by Youths at 826LA, and also very cute and upbeat.
65. “Extraordinary Machine”
“I’ll make the most of it; I’m an extraordinary machine” has gotten me and maybe you through more than we would care to admit! 2019 was a long year, wasn’t it.
64. “I Can’t Wait to Meet You”
This song is cute! Not distressing!
63. “Waltz (Better Than Fine)”
This is so soothing. The next time you’re spiraling about what you’re doing with your life, please allow the tiny, enormous-eyed specter of Fiona Apple to perch on your shoulder and croon “I don’t believe in the wasting of time, but I don’t believe that I’m wasting mine.”
62. “I Want You to Love Me”
The naked want here forms such an intense undertow, and the precision and refusal to embroider or dramatize it makes it something that feels like a whole new emotion. It isn’t sad, it isn’t needy or mourning, even though it its articulation it acknowledges that she isn’t being loved right now; it’s such a Fiona song in that its almost unbearable honesty, directness and self-awareness around a basic human experience just bowls you over. Something about the baring of something so primal with a total absence of shame feels like something close to like, nirvana?
61. “Everyday”
Sweet!
60. “Slow Like Honey”
Not actually that sad, just downtempo! Thinking about how your ex definitely still has sex dreams about you because they aren’t over you is kind of a positive, really.
59. “Shameika”
Shameika is right! Also “Hurricane Gloria in excelsis deo” is such a thrilling and bananas and perfect line here. Would like to tip a hat to the Genius lyrics commenter who noted “serotonin receptors activated.”
58. “Tymps (The Sick in the Head Song)”
When you know your ex is still having sex dreams about you but part of it is because you keep having sex with them. Complicated; not all bad!
57. “On I Go”
“This was my version of the Vipassana chant that I sang in jail.” I love this bitch
56. “Periphery”
On cutting your losses, an admirable practice! “All that loving must’ve been lacking something
If I got bored tryin’ to figure you out” is the sickest burn.
55. “Drumset”
This is great because it’s like two songs in one: the one in the lyrics about abandonment and wondering why the people you love don’t care enough to stick around and try harder to make it work, and then the one that it deepens into when you hear the impetus for it: “…[the band and I] had this little argument and then they took some of their instruments away. I misinterpreted it as that they were pissed at me and that they weren’t going to come back. That was me sitting there going, “Aw, nobody loves me.” Amy didn’t actually take the drums from my house. She took them out, but it’s because she had a gig. I took it to mean everybody was mad at me.” Now it’s a song about how sometimes the stories we tell ourselves about how bad and alone we are don’t have to be true! And also that she still recorded this song, with the same band it was about, which feels very tender and intimate to me, because they’re still in each others’ lives, duh.
54. “Sleep to Dream”
Same energy as Nelly Furtado saying “pay attention to me, I don’t talk for my health.”
53. “O’ Sailor”
A striking evocation of the sentiment “why did you have to go and do that,” arguably an emotion all on its own.
52. “Across the Universe”
Unfortunately I do black out completely any knowledge of or opinions on Beatles songs; this one sure does exist, though! What is it about. Who’s to say? Not me!
51. “You Belong to Me”
This seems like it should be sadder than it is! Maybe the lesson here is that songs ostensibly about sleeping with your ex aren’t actually that sad because it’s just sort of a fact of life.
50. “Get Gone”
Singing along with “and I do know what’s good for me” is legally the equivalent of 3.5 months of therapy! Did you know.
49. “Under the Table”
The spiritual successor to “I do know what’s good for me”: I won’t shut up, I won’t shut up; don’t push me, cookie, don’t you push me!
48. “Largo”
The feeling of being a little fucked up but also being held by a network of loved ones through it and being grateful for having them? Bittersweet!
47. “The First Taste”
When will your crush text you, but moreso!
46. “Please Send Me Someone to Love”
Someone to love would be nice; she isn’t wrong! Just sort of an objectively true observation.
45. “Get Him Back”
This is fucking unhinged!
44. “Limp”
Not so much depressing, I don’t think, as “internal soundtrack to your decision to pursue vengeance and right the wrongs done to you.” Godspeed!
43. “A Mistake”
Making mistakes is fun! This song is fun.
42. “Fetch the Bolt Cutters”
A song about liberation! I somewhat cornily imagine this as Fiona getting up and walking off the set of the Criminal video without explanation. Inspirational! Aspirational!
41. “Window”
You do need to break the window sometimes! I’m glad someone said it!
40. “To Your Love”
Fiona has an entire roster of songs that are just about the paradoxical quandary of wanting to experience intimacy and connection but refusing to allow anyone enough access to her to build it, and then hating herself for it and apologizing profusely before returning immediately to the same behavioral pattern; this is one of the less sad versions of it. The vibe is more sort of a heads up: “Now you have it! So, tell me, baby… What’s the word? Am I your gal or should I get out of town?” Just a quick check-in, you know? Did we mention she’s a Virgo.
39. “River, Stay Away from My Door”
Stay away from it! Seriously, she’s just asking you to stay the fuck away from that one door.
38. “Container”
“I was screaming into the canyon at the moment of my death” is a bummer of a line. This song was written for The Affair, a mediocre-sounding show that features McNulty from The Wire that I will never watch. It’s a pretty good song though.
37. “Dull Tool”
Less a sad song than a thoughtful, sober meditation on dating men.
36. “I’m in the Middle of a Riddle”
I have no idea what’s going on with this one; it is charming as hell and also sort of unsettling. Maude feature!
35. “Sally’s Song”
I’m not a Nightmare Before Christmas person and feel minimal emotions about this song. Feel free to tell me I’m wrong.
34. “I Know”
Setting boundaries around your level of involvement with someone who is still in a monogamous relationship for the time being is healthy and positive, even if it is disappointing!
33. “Ladies
The tension here is between the magnanimous lyrics and the sort of grandiose, swerving delivery that almost feels like a sloppy drunk at the bar – it’s a little unnerving, and makes it less clear whether Fiona’s addressing an imagined woman or herself, or both. Some things you say out loud because you’re trying to get yourself to believe them! “Nobody can replace anybody else/ So it would be a shame to make it a competition/And no love is like any other love/ So it would be insane to make a comparison with you.”
32. “Red Red Red”
This is a song about being in love with someone unavailable and realizing how tired you are. Fiona Apple’s “Space Cowboy,” if you will. It’s sad, but the “exhausted” flavor of sad.
31. “Werewolf”
“You were such a super guy til the second you get a whiff of me” is truly chilling! Yikes!
30. “Regret”
You could do a dissertation on gendered dynamics in caretaking and illness or you could just listen to this song, same difference really.
29. “Every Single Night”
A paean to debilitating anxiety. Stressful.
28. “Relay”
“I resent you for being raised right” really just splits me right open.
27. “Love Ridden”
This was the first breakup song I ever added to my internal roster of Breakup Songs and at 17 it felt heartbreaking; now it feels sad but also tender — ‘if I need you, I’ll just use your simple name,’ not that you’ll never call for them again.
26. “The Way Things Are”
The self-awareness here is so gutting! “I wouldn’t know what to say to a gentle voice; it’d roll right past me.”
25. “Cosmonauts”
I don’t know what it is about this song, but it is so intense for me that listening to it or thinking about it for too long feels like looking directly into the sun? “Be good to me, it isn’t a game.” For all Fiona’s precise evocation of need and desire and self-denial etc etc, it feels so rare and so shockingly intimate to hear an actual ask, a vulnerable request: “Be good to me.” Woof!
24. “Not About Love”
An industry secret is that sometimes when someone strenuously insists something is not something, it’s because it is very much that thing. (Not sure what the industry is here; lying?) Sometimes, though, it’s not! A very sad feeling is when you can feel yourself falling out of love and you wish you weren’t but you are. It’s sad right now thinking about it, isn’t it! Told you so.
23. “Valentine”
Pining! You love to see it.
22. “Rack of His”
This is a song about wanting to spend all your time with someone because you’re crazy about them and realizing they don’t really want to hang out with you even as a minor distraction, which sucks. Actually the “them” here is sort of misplaced, as this feels very specifically a song about men. This is not a good feeling! It feels bad.
21.”Daredevil”
This is only medium despair-inducing until the last verse, which is a high level of despair-inducing, I would argue.
20.”Parting Gift”
The refrain of this song is a good sort of worry stone to roll around in your pocket when you’re starting to let go of something that was never gonna work out but honestly it’s the image of someone being “as sincere as a dog” when kissing you (badly) that I think I have thought about, no exaggeration, every single day since I first heard this song at maybe 16.
19. “Please Please Please”
“Me and everybody’s on the sad same team, and you can hear our sad brains scream.” A song about when six different people send you the same niche Instagram meme about trauma recovery.
18. “Fast as You Can”
“You think you know how crazy I am” is a truly harrowing mood. This one goes out to everyone who has ever been mistaken for a manic pixie dream girl and then abandoned in horror when it turned out they were a real person with real problems!
17. “For Her
This feels like When the Pawn… era Fiona, which is great and also sort of terrifying in its intensity. I feel like I can only listen to this song once a week, possibly, until I build up a tolerance.
16. “Jonathan”
I am undone by the plea to “tolerate my little fist.” Just tolerate it! Just t o l e r a t e.
15. “Oh Well”
Every single verse of this is like getting clocked in the side of the head with a Yankee candle. The “oh, well!” Come the fuck on.
14. “Newspaper”
I have never heard anything like this song, really — about the strange kind of triangulated metamour relationship formed between two women who have been harmed by the same man and who know about each other only by reputation, but who will never be in contact because of the way he’s worked to pit them against each other. How it’s competitive but also tender and how those women share something no one else can ever understand in a way that’s almost romantic. It’s a lot to take in! Maybe try lying on the floor.
13. “On the Bound”
Does the “baby, lay your head on my lap one more time” get me every time? Sure fucking does!
12. “I Walk a Little Faster”
God, every time she covers a Cy Coleman song it is the perfect soundtrack to just staring at the wall while a slow-motion reel of your deepest, quietest regrets unspools. This youtube comment sums it up well: “One day I got drunk and decided to play this playlist and sleep. In my sleep this song came over and in my soporific state I started crying. I don’t know why this very song was able to persuade a few tears from my otherwise hollow existence but the feeling was incomparable. I have hardly ever felt so strongly about any song. Can never forget this song. Can’t ever forget about you”
11. “Sullen Girl”
This song is so fucking sad! Full stop.
10. “Pale September”
This song is like taking a Willy Wonka magic candy that gives you the VR experience of lying on the floor, staring at your ceiling, thinking quietly about loss while you take the bus to Publix.
9. “Paper Bag”
“I know I’m a mess he don’t wanna clean up!” Jesus Christ, people!
8. “Shadowboxer”
I think two emotional registers Fiona Apple’s work gets at very deftly are anger and exhaustion; how grief or trauma or pain engender helpless rage and also how they wear you down, the amount of energy they involve, and this song is about both — the endless project of bracing yourself, getting ready. Bonus points for the association with Julien Baker’s “Shadowboxer,” also deeply fucking depressing.
7. “Left Alone”
The quintessential Fiona Apple question, a heartbreaking one: How can I ask anyone to love me when all I do is beg to be left alone? Jesus!
6. “Criminal”
Is the song sad? Yes, duh. Is it even sadder when you think about the context of a teenage Fiona’s intense scrutiny and sexualization around that song and video? Also yes!
5. “Frosty the Snowman”
We don’t talk enough about what an upsetting song Frosty the Snowman is! It’s fucked up!
4. “The Child Is Gone”
Despair is the word for this! It just is. “I don’t want to talk because there’s nothing left to say” is such a deep, bottom-of-the-barrel kind of despondency.
3. “Carrion”
A truly indescribably beautiful and courageous thing that humans do every day of their lives is choose to love things and people — not just to experience the sensation of love, but choose to cultivate it and rebuild it each day, even when it’s hard or uncertain or just tedious. The opposite of that choice, to decide to let something go and stop tending to it because there’s no point any longer or you’re just too tired, is an indescribably miserable one.
2. “Never Is a Promise”
Also one of the worst feelings on earth: when you have realized something is impossible or futureless but someone else has not yet, and you have to carry that knowledge all by yourself, humoring their optimism, while waiting patiently for them to come to the same conclusion. What an endless index of types of pain fostered by the connection or lack thereof between people! What a world!
1. “Why Try to Change Me Now”
Jesus Mary and Joseph, this song is a tool of emotional warfare. Maybe the lowest low of human existence isn’t violence or heartbreak or indelible shame but the quiet resignation underlying them? Maybe it’s just the feeling of trundling along a sidewalk in late autumn as it gets dark and really internalizing that you’ll never really be ok with the worst parts of you and if you aren’t then why would anyone else be? The wry, rueful cheerfulness of posing it as a question makes everything indescribably worse. I listened to this on repeat for an hour once and I will never be the same as I was before doing so. If you share intimate knowledge of this experience, you are in my prayers.

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