20. Across the Universe (1998)

You could easily fill a Top 20 with Apple’s original compositions, but this Beatles cover deserves recognition for arguably besting the original. Recorded for Pleasantville, the 1998 film by Gary Ross, Apple’s limpid delivery brings the lovely melody to the fore and imbues it with emotion.

19. Fetch the Bolt Cutters (2020)

The title track of Apple’s long-awaited fifth album quotes from the police procedural The Fall, as Gillian Anderson’s character cuts free yet another female victim of a serial killer. The song evokes that dark inspiration in its shifting, unsettled sound and Apple’s spoken-word delivery before falling into a supportive groove, representing her freedom. (The barking dogs after the Kate Bush nod is a nice touch.)

18. Criminal (1997)

Still Apple’s highest-charting single, Criminal garnered attention for its video directed by Mark Romanek (One Hour Photo, Never Let Me Go). It presented the then 19-year-old singer as an unapologetic man-eater in a state of undress. The song is much more nuanced, capturing Apple’s ambivalence about the ease with which she takes advantage of a good man’s love, and her desire for redemption.

17. Left Alone (2012)

Driven by clattering drums and a jaunty – if faintly foreboding – piano line, Apple’s performance keeps the wheels from coming off this wagon. She brings all her vocal acrobatics to bear in tussling with what is perhaps her defining question: “How can I ask anyone to love me when all I do is beg to be left alone?”

16. Slow Like Honey (1996)

Apple’s debt to jazz and cabaret can be glimpsed throughout her catalogue, but this is the closest she has come to writing a standard of her own. The adult-contemporary polish to the production belies Apple’s age – she was just 18 when her debut album, Tidal, came out – but serves her self-possessed lyrics and smoky delivery.

15. Ladies (2020)

Much of Fetch the Bolt Cutters deals with Apple’s preoccupation with other women as a mirror for her insecurities and her strengths. Ladies is the most explicit on the theme, and also the most playful, with Apple extending sisterly solidarity to her ex’s new lovers. Backing singers amplify her magnanimous message, even as Apple’s muttered outro casts doubt over whether it will be received.

14. Sleep to Dream (1997)

Kanye West once called “I have never been so insulted in all my life” one of his favourite opening lines to a song. He was wrong about those being the opening lines, but not about their impact. The second single from Tidal lurches into view with a thundering bass drum, while strings lend an undercurrent of unease to Apple’s sultry delivery.

13. Hot Knife (2012)

Opening with Apple’s voice, unaccompanied but for rolling timpani drums, before building into a hypnotic round, Hot Knife makes clear her innate – and idiosyncratic – grasp of melody and rhythm. It’s at once supple and skeletal; the piano darts in and out, always defying expectations, while the earworm burrows deep.

12. A Mistake (1999)

With its tastefully distorted guitar and muted keys, A Mistake verges on radio-friendly alt-rock, but Apple gives it bite, boldly aligning with her most destructive tendencies. Just as you’ve bought into her as an unapologetic bad girl, “as full as a tick” at others’ expense, Apple complicates the picture, admitting that she finds it harder to cast off external judgment than she’d like.

11. Every Single Night (2012)

What begins as a twinkly lullaby dips in and out of turbulence as Apple does battle with her duelling desires to “feel everything” – and also find some peace. The bright melody makes light work of her nocturnal tossing and turning: “Every single night is a fight with my brain.”

10. Werewolf (2012)

In this measured relationship postmortem, Apple decides against going scorched-earth in favour of taking responsibility for her part in creating the toxic dynamic. Werewolf is bracing yet sanguine, with the chorus’s reassurance – “Nothing wrong when a song ends in a minor key” – borne out at the end.

9. Fast As You Can (1999)

Fast As You Can bolts out of the gate with dissonant piano, skittish percussion and Apple’s warning to a would-be lover: “It’s so sweet you think you know how crazy, how crazy I am,” she crows. The strings-soaked midsection, switching to a lilting 6/8 time signature, dangles the possibility of an easier road, but it’s only a fleeting reprieve before she lets “the beast back in”.

8. Shameika (2020)

More straightforwardly autobiographical than Apple’s typical mode, Shameika churns with restless adolescent rage. It recounts how a classmate saw through her defensive shield and stuck up for her against bullies, changing her self-perception and the course of her life. The chaotic piano dropping out at the lightbulb-moment – “Shameika said I had potential” – underscores its impact.

7. Periphery (2012)

Having declared the music industry to be “bullshit” at the 1997 MTV music awards, here Apple reiterates her disdain for convention, addressing a man who chooses an easy life over one shared with her. However, her lusty delivery and strident piano make it clear that, after 15 years, the burden of individuality has become easier to carry. The propulsive rhythm sounds like feet briskly making tracks over gravel; in fact, it’s duct tape, tearing.

6. Cosmonauts (2020)

Even at her best, Apple’s songwriting is tightly wound and even claustrophobic, reflecting her inner monologue. In Cosmonauts, the energetic peak of Fetch the Bolt Cutters, she takes a step back and directs her formidable powers outwards. Originally intended for Judd Apatow’s 2012 film This Is 40, it’s cinematic in its depiction of the peaks and troughs of long-term love.

5. Get Gone (1999)

The penultimate track on When the Pawn … begins as Apple’s kiss-off to an ex-lover over forlorn piano. But she doesn’t stay bruised for long, turning her attention inwards as she reckons what to take from this relationship. You can hear her resolve build with each chorus, culminating in a blaze of defiance: “I do know what’s good for me.”

4. I Know (1999)

Apple doesn’t always set out to showcase the beauty of her voice, but this smoky jazz number, the closer of When the Pawn …, makes it abundantly obvious. The song itself is impeccably written – it’s easy to imagine it being the highlight of any piano-bar set – and the strings give it a timeless quality.

3. Valentine (2012)

Used to devastating effect in Lena Dunham’s Girls, Valentine sees Apple heartbroken, unwilling and unable to move on – “a fugitive too dumb to flee”. A bare-bones bed of piano and double bass puts the focus on her lyrical imagery; every line can break your heart.

2. Paper Bag (1999)

Earning Apple a best female rock vocal performance nod at the Grammys in 2001 (she lost to Sheryl Crow), Paper Bag packs the heavy weight of disillusionment into a deceptively understated package. The Beatles-esque brass and shuffling drums are almost whimsical, but pulled into line by her weary vocal, conveying her bitter disappointment that yet another man has proved “just a little boy”.

1. I Want You to Love Me (2020)

On the opening track of Fetch the Bolt Cutters, Apple wills a relationship into being – and the tensions play out on the piano, her swirling right-hand and thundering left mirroring her oscillations between uncertainty and resolve. “I hope that you love me” hints that it might all end in tears, but – having previously been inclined to self-destruction or paralysis in love – here Apple is in full possession of her powers, plus a zen-like clarity. In four minutes she projects backwards and forwards through time, and past her own death, to summon courage in her conviction that an intermittent love is nevertheless worth fighting for. The effect is bewitching, and undeniable.