20. It Happens Every Day (1983)
As an album, Hello Big Man was all over the place: reggae tracks recorded with Sly & Robbie, very early 80s world music experiments, slick MOR. Its one undisputed gem is It Happens Every Day, a careworn song about divorce, set to music that, beneath the 80s veneer, is like a lush late-50s ballad.
19. Hold Out Your Heart (2008)
Simon has hardly been idle in her 70s – a second volume of memoirs was published in 2019 – but her last collection of new songs, the Latin-flavoured This Kind Of Love, came out 13 years ago. Hold Out Your Heart is warm and sweet, enough to make you wish she would release more.
18. Haven’t Got Time For The Pain (1974)
Hotcakes saw a pregnant Simon beaming from the cover. The contents are melodically rich, but the lyrics about domestic bliss are a bit runny: you miss the steely eyed narrator of You’re So Vain. The nailed-on, mid-70s soft-rock anthem chorus of Haven’t Got Time For The Pain, however, is fantastic.
17. Jesse (1980)
The Come Upstairs album was a concerted effort by Simon to embrace new wave. Some of it is bizarre – in the unlikely event you want to hear a Carly Simon track that sounds a bit like Devo, hasten to Them – but the vaguely Springsteen-esque Jesse is a triumph: killer chorus, economical storytelling.
16. We Your Dearest Friends (2000)
Simon has released more Great American Songbook standards than original material in recent years, but her own writing is as sharp as ever. Or possibly even sharper, as evidenced by the chanson-like, savagely funny We Your Dearest Friends, on which a tableful of dinner-party guests relentlessly trash an absent acquaintance.
15. That’s The Way I Always Heard It Should Be (1971)
Simon’s eponymous 1971 debut is an artist finding her feet, tending towards country-ish arrangements which don’t suit her voice. But her first hit single is great: a surging, epic, wary depiction of marriage – “the couples cling and claw and drown in love’s debris” – from a woman declining to say “I do”.
14. We Just Got Here (1990)
Better Not Tell Her, the hit from Have You Seen Me Lately, was Simon in full-on, post-divorce lock-up-your-husbands mode, but its closing track was something else: a beautifully observed, subtly orchestrated, gorgeously bittersweet song about a couple facing life together after their children leave home.
13. Tranquillo (Melt My Heart) (1978)
Umpteen artists pivoted towards disco in the late 70s, but Carly Simon did it with particular style, as evidenced by the Arif Mardin-produced Tranquillo: five minutes (in its 12in mix) of supremely funky bass, spiralling vocals, soaring choruses and, improbably, a lyric about trying get a small child to go to bed.
12. Playing Possum (1975)
The standout title track of a very patchy album, Playing Possum is a perfect example of Simon’s ability to incisively skewer the boomer generation at various points in their history. A depiction of a former 60s radical now comfortably settled, its concluding question – “Are you finally satisfied?” – seems to be as directed at the narrator as at her subject.
11. Anticipation (1971)
Nine months after her debut, Anticipation was a vast leap forward, defining Simon as a plain-speaking, distinctly un-hippy-ish, very New York brand of confessional singer-songwriter: the title track found her waiting for her current boyfriend, Cat Stevens, to show up, while already consigning their relationship to history: “These are the good old days.”
10. Actress (2000)
From her home-recorded album The Bedroom Tapes – an overlooked return to prime form – Actress is the kind of Simon song you could easily imagine Taylor Swift (a self-confessed fan) performing: a witty sideswipe at the pursuit of fame, smart enough to reserve a degree of empathy for its protagonist. Also: fantastic chorus.
9. The Right Thing To Do (1972)
An album stuffed with songs about unrequited crushes, relationship woe and dodgy exes, No Secrets nevertheless opens with a heartfelt, breezily uplifting declaration of love. It flows so easily – driven by the congas of Ray Cooper, “the Jimi Hendrix of percussion”, according to Elton John – you scarcely notice how melodically complex it is.
8. Never Been Gone (1979)
From the album Spy, its hushed, vaguely hymnal sound the counterpoint to rocky hit single Vengeance or its disco-infused title track, Never Been Gone is one of the hidden gems of Simon’s catalogue. A 2009 re-recording has a Neil Young-ish lilt, but the piano-led original best fits the lyric, about home as an escape from the world.
7. Like a River (1994)
The gut-punching emotional zenith of her concept album Letters Never Sent, Like a River tackles the death of Simon’s mother and the complexities of her family relationships – sibling squabbles over her late mum’s jewellery are “all a metaphor for what was wrong with us”. The single version, which lops off the OTT operatic coda, is the one.
6. Nobody Does It Better (1977)
The last of the classic Bond themes – and “the sexiest song ever written”, according to pop’s legendary king of raunch, Thom Yorke from Radiohead – Nobody Does It Better is an incredible piece of songcraft, its impact amplified by the fact that Simon sings it with total lust-wracked conviction.
5. Boys In the Trees (1978)
It made sense that Simon named her excellent autobiography after the beautiful acoustic title track of her 1978 album, a haunting, unsentimental exploration of memory, gawky adolescence and “the silent understanding passing down from daughter to daughter” about what would subsequently come to be termed male privilege.
4. Legend In Your Own Time (1971)
On which Simon first unleashed one of her characteristic songwriting styles, the alternately affectionate and withering pen portrait of an ostensibly successful (and clearly quite hot) man. More than a dry run for the peerless You’re So Vain, it’s a fabulous song in its own right, filled with gloriously unexpected twists in its tune and mood.
3. Coming Around Again (1987)
Coming Around Again became a Mellow Magic FM perennial, but beneath the super-smooth MOR production lurks a fabulous, genuinely moving song that tackles a subject pop tends to shy away from – the stresses of maintaining a longstanding relationship amid the chaos of parenthood – without succumbing to syrup or schmaltz.
2. Why (1982)
Incredibly, a flop in America, Why was a final burst of genius from the original incarnation of The Chic Organisation. While the lyric about infidelity was clearly in Simon’s wheelhouse, the reggae-influenced groove was theoretically out of her comfort zone. No matter: Why works to stunning effect.
1. You’re So Vain (1972)
If Carly Simon had never written anything other than You’re So Vain, she would still be famous. It has spawned nearly 50 years of speculation over its subject, but no one would have been interested in who it was about if it wasn’t such an incredible song. Everything is perfect – the atmospheric, attention-grabbing intro; its balance of wordy intelligence and pop smarts; Paul Buckmaster’s superb string arrangement; the flatly brilliant conceit of the chorus; the cocktail of waspishness and affection in the lyrics, which leave you simultaneously horrified by its subject’s smug, philandering bullshit and weirdly impressed despite yourself.