Are your knees fit for purpose? Can you listen to new music with neither a derisive snort of recognition nor a shudder of sheer atavistic bewilderment? Do you feel that things are worth achieving, and that there is much joy out there waiting to be discovered?

If you answered ‘yes’, stop reading now. This post is not for you.

Nik Kershaw ‘Dancing Girls’

Soul destroyed by life’s demands with nothing to believe
Our hero sits with head in hands and heart upon his sleeve

Yep, that pretty much covers it, but how can someone so young sing words so sad? Perhaps Kershaw had somehow foreseen his fate as a nostalgia-show stalwart, gamely taking the piss out of ‘The Riddle’ at the behest of TV producers too young and/or stupid to appreciate how snugly his music fitted the mood of Cold War Britain. His dignity, like his hair, was something he deserved to keep.

Guillemots ‘Falling Out Of Reach’

Your thirties in a song: an appropriately easy-listening account of how it feels when you’re no longer the centre of your own life. The last verse provides the final, cruel twist:

You just need a rest, you just need your friends
But they’re slowly falling out of reach

Paul Simon ‘Train In The Distance’

The perfect lyrical encapsulation of ‘wherever you go, there you are’, by a master of painting from life. Just pipped ‘Slip Slidin’ Away’ into this list.

Christopher Cross ‘Sailing’

Yes, it’s about sailing, but it’s not about sailing, it’s about escaping. And, perhaps, getting into Radio 2. You can reach the beach in your Mazda or your mind.

Joshua Radin ‘Underwater’

One step on from ‘Sailing’ is this strangely perky acoustic jam about hiding underwater. Radin’s high-plains falsetto gives it a redemptive, expansive feel, but the lyric always makes me think of poor Dennis Wilson, curled up on the sea bed in Marina del Rey. Wilson clearly wasn’t built for middle age and duly wiped out aged 39.

Talking Heads ‘Once In A Lifetime’

‘Well, how did I get here?’ David Byrne’s inspired lyric is the sound of a man suddenly waking up and looking around him, as if life so far has been nothing more than a dream.

Which brings us nicely on to…

Jakatta ‘American Dream’ (Joey Negro Club Mix)

Do you feel, like Lester Burnham, that you’ve lost something, but you’re not exactly sure what it is? Do you know you didn’t always feel this… sedated? Well, I can’t help you with that, but if you stick this on your Shuffle it’ll keep your mind off your knee pain as you grind out another mile of suburban pavement.

John Parr ‘St Elmo’s Fire (Man in Motion)’

I kept hearing this song for decades without having the faintest notion what Parr was on about. At 42, I finally understand: it’s a middle-aged man’s fantasy of redemption. ‘Once in his life, each man has his time… and MY TIME IS NOW!’ he bellows, almost convincing you that if you drop 20 grand on a Harley and ride towards a sunset, you’ll have something ‘burning inside you’ other than acid indigestion.

Steve Winwood ‘While You See A Chance’

Superficially similar to the previous selection, but this track offers self-examination in place of self-indulgence. Winwood’s peerless lyric touches on world-weariness (‘how the endless road unwinds you’), self-doubt (‘even you don’t quite believe you’) and inescapable self-responsibility (‘because it’s all on you’). Winwood exhorts you to ‘find romance’, particularly in the glorious coda, but this feels like a nod to soul songwriting convention, because there is only ‘you’ in this lyric. ‘Romance’ is a feeling that you have lost.

Tracey Thorn ‘Hands Up To The Ceiling’

The feeling alluded to by Steve Winwood is given full and devastating expression by Tracey Thorn, looking through the music and certainty of her student days as if peering through the wrong end of a telescope. Like the persona in ‘Once In A Lifetime’, she seems genuinely puzzled by where the intervening years have gone, and why. The song hangs on to its closing subdominant for bar after bar, waiting for an answer that never comes.

Peter Gabriel ‘Indigo’

It’s too late, this model’s out of date
Got every spare part, but there ain’t much heart inside here
Not like the start…

Gabriel was only 28 when he penned this inscrutable, infinitely world-weary lyric. I wonder how he feels about it now. Personally, I like it a lot more than when I first heard it at 15. A strange, disjointed melody and progression gives the song the feel of a rickety, worn-out contraption, but it finds its resolve on the entry of the drums. The vocal, relatively unaffected for this stage in Gabriel’s career, steadily rises in intensity, from melancholy to desperation. A minor masterpiece.

Pet Shop Boys ‘Invisible’

This was written after a friend of Neil Tennant’s observed that women over 40 are effectively invisible at social functions. His detached, self-effacing vocal drifts through a slowly cycling electro arrangement with a Satie-like atmosphere. ‘Am I really even here?’ he asks himself, like a tree falling in the forest.

Carpenters ‘Rainy Days and Mondays’

If nothing is really wrong, but you’re feeling like you don’t belong, it’s time to listen to Karen Carpenter. The sadness in her voice transcends her life, and your life, and everyone’s. It fills the world.

Amy Mann ‘Wise Up’

It’s not what you thought when you first began it
You got what you want
But you can’t hardly stand it though

Magnolia is a funny old film, at once totally natural and ludicrously contrived. Maybe that’s what happens when you start with songs rather than stories or characters. (Paul Thomas Anderson based his script on Mann’s music.)

The scene where each main character sings a line from this song (below) is stone-cold genius. Anderson shoves the artifice right in your face, daring you to stop believing in it, but you don’t. Instead, you start thinking about which line in this song fits your own life.

Jon Brion ‘Little Person’

Another ‘escaping’ song, this time about finding someone to escape with. But the ‘someday, maybe somewhere, maybe somewhere far away’ makes clear that it’s an impossible fantasy, like Bobby Darin’s dream lover beyond the sea.

The C90s ‘Shine a Light’ (Flight Facilities remix)

In Grand Theft Auto 5‘s Michael De Santa, middle-aged gamers finally had a hero they could relate to – a paunchy pop who listened to Phil Collins on his iPod, wore petrol-blue polo shirts and had gained the life he wanted but lost himself along the way. In this ludicrous early ‘mission’ he jealously assaults his wife’s yoga teacher, rashly samples his son’s Special K, gets briefly abducted by aliens and ends up floating above Los Santos (rather like The Dude in Big Lebowski) in a sort of psychedelic colour vortex. The verses shake their head over Michael’s identity crisis while the chorus offers him some crumbs of validation.

Mark Hollis ‘The Colour Of Spring’

‘Set up to sell my soul, I’ve lived a life of wealth to bring.’ Serious as ever, if not a little melodramatic, Hollis sums up the way you feel after two straight decades at work. But green shoots always return. Music so good you forget about growing old. (Note that the track begins with 19 seconds of silence.)

Aqualung ‘Magnetic North’

Dip a toe into our middle age
Dip a toe and in we’ll go…

Like fellow master melodist Paul McCartney, Matt Hales hasn’t been afraid to follow his songwriting talent into marriage-and-kids territory. Over trademark piano, he develops his ocean/navigation theme so deftly you hardly notice it washing over you, bringing with it metaphorical flotsam from ‘autochord’ to ‘motorcade’. This song is that rare beast, a love song for someone who, rather than being some idealised muse or fantasy seductress, is clearly a wife and mum – someone who ‘keeps this old ship on course’, without whom ‘we would all be lost’.

Tags: Amy Mann, Aqualung, C90s, Carpenters, Christopher Cross, Flight Facilities, Guillemots, Jakatta, John Parr, Jon Brion, Joshua Radin, Mark Hollis, Nik Kershaw, Paul Simon, Pet Shop Boys, Peter Gabriel, Steve Winwood, Talking Heads, Tracey Thorn