Being creative is easy when you're young - you have nothing to lose and little to live up to.
Musicians often excel in their early outings but struggle with the Muse as the indignities of middle-age, the challenge of matching their early signature work and the grind of album/tour/album kick in.
As we all know, some aren't able or willing to find a way through the drugs and general misadventures - and as 90s rapper NAS said best, Life's a Bitch - (and although, like most rap and hip hop artists, he's too "young" to qualify - he's only 44 - few would argue his greatest work lies a way back in 1994's Illmatic.)
So, just as we never got to read F Scott Fitzgerald (gone at 44), Nathanel West (37) or David Foster Wallace (46) confront the big 5 0 and the troubled hinterlands thereafter, so we'll never hear how Jeff Buckley (30), Amy Winehouse or Kurt Cobain (both members of the gone-at-27 club) or Chris Whitley (45) dealt with ageing and creativity as the successes and temerity of youth fade in the rearview mirror.
But there are artists out there who have done, and continue to do, their best work in their later years - not just making good records but ones that stand with their best.
It's hard to sort the chaff from the wheat when everyone of a certain age is on the comeback trail: Mavis Staples, Leonard Cohen (RIP), Emmylou Harris, Lou Reed (RIP), Tom Waits, Paul Simon, Loretta Lynn, Merle Haggard (RIP), Roseanne Cash, the Jayhawks, Chrissie Hynde have all released well-received records post-50.
But here's a starting point.
Time Out Of Mind
Bob Dylan (1997)
Delve down and late-period Dylan has some real gems.
There are songs written in the last 25 years (Dylan's now 75) that are the equal of anything from the 60s or 70s (Scarlet Town, Aint Talkin, Forgetful Heart) but the great record of the period is Time Out Of Mind. The most fun and criminally underrated is 2009's Together Through Life, most of it co-written with the Grateful Dead's Robert Hunter.
Dylan was 56 when he went to Miami to record TOOM. The king of reinvention had hit a roadblock, writing-wise. His last album of original material was the awful Under The Red Sky but now he had his best set of songs since 1978's Street Legal.
But it was choosing Canadian producer Daniel Lanois (Lanois had also helmed Dylan's last commercial success, 1989's Oh Mercy) that made TOOM such a defining record. Lanois wasn't a yes-man. He pushed Dylan, even suggesting he rewrite lyrics. The sessions were fraught, 12 players (often two drummers) in the studio, and most of it was tracked live. Dylan wanted it to sound as visceral as the blues records of the 50s that he loved.
Lanois complied - but added a spooky reverb-drenched menace. Check out Lanois' book Soul Mining for an in-depth look at recording this late masterpiece.
James McMurtry (2015)
This was +Plus's 2015 album of the year. And time has only heightened its power. McMurtry was 53 when this was released - and if good reviews were currency he'd be the richest songwriter in Austin. He isn't. But Complicated Game is a superb record and sonically more adventurous. He'd been producing his own albums for years but let Mike Napolitano and C.C. Adcock helm this one. Good call. It's a more acoustic record and one whose songs deal with relationships: work, romance and family.
The record was tracked in pieces. McMurtry would head out on the road, leaving Adcock and Napolitano to flesh out his simple guitar and vocal tracks. Guest musicians include Benmont Tench of the Heartbreakers and Ivan Neville.
An excellent piece in the LA Weekly suggested that west and east coast liberals listen to McMurtry's music to understand Trump's unexpected victory; for - despite McMurtry being a vociferous opponent of Trump, his songs capture bewildered rust belt anger like no other.
From the disillusioned soldier who returns to the barren landscape of South Dakota to the self-harmer of album closer Cutter (which wouldn't be out of place on Lou Reed's Blue Mask), to the small-town fishermen who help an old-timer fish illegally in the album's finest track, Carlisle's Haul , McMurtry's characters lead the song. There are no heroics, and the story's told in plain language.
Much has been made of the fact that novelist Larry McMurtry (Lonesome Dove) is his father, but James is arguably a sharper writer.
He's spoken of these characters "enduring, not fading away. Standing against the current that wants to wash you away but can't, yet."
And in McMurtry, and the songs on Complicated Game, they have found their finest chronicler.
Washington Square Serenade
Steve Earle (2007)
At the last Earle show I saw, he stopped midway through the set and said he avoided looking out at the audience these days because all he sees are hundreds of ugly, balding middle-aged guys just like him staring back. It got a good laugh but Earle is one of the few who has kept the quality high as the years pile up (his hero Townes Van Zandt, with just a few exceptions, wrote all his great songs young).
This, released when Earle was 52, is one of his best. He's currently writing a Broadway musical based on this record which covers his leaving Nashville and settling in New York with his (then) new wife.
It's also the first record he recorded on Protools, tracking songs in his NY apartment and finishing them off at nearby Electric Lady studios with Dust Brother John King producing. Drum machines drive it and that disonance casts his alt-country stylings in a refreshing, modern light.
It helps that Earle turns in some great songs - Down Here Below, Days Aren't Long Enough celebrating his marriage to fellow artist Allison Moorer and Tennessee Blues among them.
Of course the marriage was toast within a few years but Earle's still based in New York and this record is a wonderful celebration of his (then) new hometown.
Push the Sky Away Nick Cave (2013)
Released when Cave was 56, this is a great sounding record - listen to that rhythm section. Writing-wise, Cave tones down the schtick but keeps the humour and carnality. His finest yet.
Key tracks Higgs Boson Blues, Water's Edge, Mermaids
Locked Down Dr John (2012)
We can thank The Black Keys' Dan Auerbach for this. He assembled the band, got the Doctor writing (along with the musicians and Auerbach himself) and hit "record" on an analog tape machine. A woefully under-rated record. Listen to that voice, and the Doctor was 72 when this was recorded. Key tracks: Locked Down, God's Sure Good.
Most Things Haven't Worked Out
Junior Kimbrough (1997)
Dirty, carnal blues, made when the great bluesman was 66. Kimbrough died in a few months later - leaving 36 children behind. His early releases get the purists salivating but this one possesses a strange, dark power - and has one of the best titles ever. Essential. Key tracks - I'm in Love, Lonesome Road
Don McGlashan (2015)
Released when Don was 56, this is his most personal and direct record yet.
Mortality, new love, change: this is a grown-up record in the best sense possible. It also contains the incandescent ballad For Your Touch.
Key tracks: Hold On To Your Loneliness, Lucky Stars, When the Trumpets Sound
Greg Fleming is an Auckland-based writer and musician