20. Fruityloop (2025)
The final track of West End Girl is as close as the album’s break-up saga comes to conciliation, which isn’t terribly close (there’s a glancing lyrical reference to fault on both sides). But in its dreamy trip-hoppy backing and the sweetness of its melody lurks something else: a sense of closure.
19. Who’d Have Known (2009)
“I ripped off the chorus … and can’t be bothered with the paperwork,” shrugged Allen of Who’d Have Known’s distinct similarity to Take That’s Shine. They let her use it anyway, and understandably so: Who’d Have Known is an entirely lovely drawing of a relationship in its early stages, that seems to gently glow with possibilities.
18. Our Time (2014)
A genuinely great song from Allen’s flawed third album Sheezus, Our Time neatly captures a sense of here-comes-the-weekend anticipation. “Bring some fags and bring some Rizlas, we’re gonna party like it’s nobody’s business,” she offers, larding her all-back-to-mine invitation with the splendidly understated boast: “I’ve got a quite good record collection.”
17. 22 (2009)
Musically, 22 offers finger-snapping post-Amy Winehouse soul given a synth makeover. Lyrically, it’s fantastic: a Ray Davies-esque character study that offers a remarkably clear-eyed assessment of societal pressures faced by women approaching their 30s. And if you want an indie-sleaze period piece, head for the Big Pink’s distorted, dubstep-influenced remix.
16. Friday Night (2006)
It made sense that Allen was at least partly responsible for the Specials’ reunion: her 2007 Glastonbury performance put Terry Hall and Lynval Golding on stage together for the first time in 22 years. Friday Night is effectively their 1979 track Nite Klub rebooted for the 21st century; dancefloor misery abounds, set to a ska rhythm.
15. Hard Out Here (2013)
The furore around alleged cultural appropriation in the video for Hard Out Here seemed to drown out the song itself. Allen subsequently dismissed it as “beige” and “saccharine”, but, a decade on, it sounds surprisingly great: a dose of fizzy, snappy electronic pop, with lyrics that – if not exactly deep – are certainly witty.
14. Knock ’Em Out (2006)
Audibly influenced by the Streets, Knock ’Em Out is a sparkling pop song – its joyous hook comes, improbably enough, courtesy of New Orleans piano legend Professor Longhair – and, furthermore, its saga of unwanted male attention contains the greatest list of brush-offs in pop history: “I’m pregnant!” “I’ve got herpes – no, syphilis!”
13. Family Man (2018)
[embedded content]
Written in 2015, as Allen’s first marriage was failing, but released post-divorce, Family Man is a self-loathing plea for a reconciliation that it quietly seems to acknowledge is futile – “I hope we’re gonna pull through / but darling I need my time away from you” – turned into a classily understated piano ballad.
12. URL Badman (2014)
Sheezus was released to bad reviews – not least from the artist who made it – but it had its moments. URL Badman launched itself teeth first at online haters. Its pitch-perfect description of a certain kind of 2010s hipster critic has dated, but the thrust – “I don’t troll, I make statements” – remains supremely relevant.
11. Everyone’s at It (2009)
A powerful, caustic dispatch from the frontline of late-00s hedonism. Those inclined to a rose-tinted view of said era might note how awful it all sounds – “when will we tire of putting shit up our noses … it just doesn’t feel right” – and the twitchy paranoia of the music, wailing siren-like synths and all.
10. Tennis (2025)
The song that turned the phrase “who the fuck is Madeline?” into an unlikely meme – and set one tabloid on an apparently successful search to discover her real identity – Tennis is a distilled shot from the lethal cocktail that is West End Girl: excruciating events described in shudder-inducing lyrical detail, against airily pretty music.
9. Littlest Things (2006)
Co-written with Mark Ronson, Littlest Things was the flipside of the breezy screw-you attitude found on Smile: another break-up song, it gently but disconsolately picks over the debris of a relationship, offering up a selection of fond, keenly observed memories. The lilting piano accompaniment comes from the soundtrack of 70s softcore porn flick Emmanuelle.
8. LDN (2006)
A supremely jaunty debut single – driven by a sample of Jamaican saxophonist Tommy McCook’s Reggae Merengue that sounds like sunshine in musical form – LDN skilfully captures one type of capital dweller’s view of their home town: endless complaining about its grottiness, insistence that it’s the best city in the world regardless.
7. Trigger Bang (ft Giggs) (2017)
[embedded content]
The first single taken from No Shame was an impressive assertion that, with her fourth album, things were back on track: a stark assessment of her hard-partying past from the perspective of the newly sober Allen. And rapper Giggs’ guest verse is superb, not least for the line: “I’m old school, fam – I know Zippy.”
6. Pussy Palace (2025)
There may have been better songs released last year, but for sheer OMG-she-went-there shock value, nothing matches the moment on West End Girl where the gloves really come off. Dirty laundry has seldom been aired with more jaw-dropping dramatic flair: that it’s set to such an addictive melody only compounds things.
5. Not Fair (2008)
“I look into your eyes and I want to get to know yer / And then you make this noise and it’s apparent it’s all over”: should you doubt that Lily Allen broke at least a little new ground, it’s possibly worth considering how many other major hit singles there have been about premature ejaculation.
4. Madeline (2025)
In which a chunk of Neil Diamond’s Girl, You’ll Be a Woman Soon is pressed into the service of a song about confronting the Other Woman. If Madeline marks the moment on West End Girl where the injured party takes charge of the narrative, it also captures the panic involved in doing so.
3. Fuck You (2009)
When Olivia Rodrigo brought Lily Allen on stage at Glastonbury to sing Fuck You in 2022, it underlined Allen’s influence on latterday pop; and what a fantastic song Fuck You is, wrapping a bitter dissection of political intolerance – alas, far more pertinent 17 years on – around an implausibly jaunty pop melody.
2. Smile (2006)
The most enduring of Allen’s early hits – more than half a billion Spotify streams and counting! – Smile was musically irresistible, thanks to its sample from the Soul Brothers’ 1966 reggae classic Free Soul. More importantly, Allen’s sweary tale of romantic revenge helped usher in a new era for women in British pop: gobbier, sharper, more relatable than aspirational.
1. The Fear (2009)
[embedded content]
Around her second album, Lily Allen was in the habit of telling journalists she had considered giving up being a pop star to open a cake shop. A similar disquiet about her burgeoning fame fuelled The Fear, which pointedly, wittily nailed the grimness of late-00s celebrity culture: she was smart enough to lyrically acknowledge her own complicity in the whole charade and equip it with a monster chorus. The four weeks it spent at No 1 suggested the British public realised something had gone wrong too: there’s something depressing about the fact that you could write the same song today without fear of irrelevance.
The Guardian
About the Author
