“It’s better to burn out
Than it is to rust.” - Neil Young, before he got old.
”I hope I die before I get old.” - The Who, only one of whom died before getting “old.”
Pop(ular) music really is a young person’s game. At least since 1949, when RCA sold a bedroom-ready record player for $12.95 and teens could finally play their music in their bedrooms, out of their parents’ earshot, no longer tied to the family record player in the living room. Before that, music for teens was more pandering, infantilizing, squeaky-clean crappe like “How Much Is That Doggie In The Window?”1 Once technology and culture and economics all aligned, suddenly there was—for the first time—music being made that was INTENDED for young people. That’s how we went from ultra-sanitized Pat Boone to the flammable danger of Little Richard.
The new popular music’s songs—see the lyrics quoted above—said it out loud: this is no place for the blue hairs. I’d say pop music chews artists up and spits them out, but I think it may actually swallow them whole before initiating a Sarlacc-type digestive timeline. Other artistic endeavors seem to be less….ageist than pop music.
For instance…
Nobody cares how old Picasso was when he painted Guernica (56) or Jacqueline (80).
And nobody cares how old photographer Richard Avedon was when he took iconic photos of Tom Ford (79) or Whitney Houston (64).

All of this—Richard Avedon and Pablo Picasso not to mention, say, Paul Cezanne and Grandma Moses—to convey the fact that some artistic disciplines look more kindly on aging than pop music does (or doesn’t, as the case may be and is). Maybe we all feel some embarrassment by proxy when we see older musicians trying to keep doing what they did when they were younger (Not that I don’t think there’s something to be said for aging gracefully and playing to your strengths, like John Prine and Bonnie Raitt. On the other end of the spectrum, the wide-eyed, Botoxed faces and wigs and who-knows-where-they-all-get-the-same-stylist2 outfits can be…a lot. “Cringe” as the kids say. See? Even I—well into my 40’s—am being snarky about age in the midst of my defense of it! That’s how ingrained the bias is.)
I toyed for a few good years with moving to Nashville. Interviewed for a few jobs, even got offered a pretty great one. There were some ambitious music business reasons behind the idea—wanting to be in a musical epicenter, hoping for a publishing deal, feeling like being closer to industry difference-makers might make a difference in my music career aspirations. But there were also some pretty attractive cultural reasons (not the bedazzled jeans) like….well, for starters, sometimes I’ll go to a family reunion or church on Sunday, and someone (with little or no malice) will ask, “So…you still playing with your little band?” in a way that feels diminishing, in a way that feels like the subtext is either “you’re not famous; why are you still doing it?” or “haven’t you outgrown that yet?” Additionally, there are some festivals and venues and opportunities that, in Utah, weren’t typically gonna go to a dude in his 40’s—my relevance as an artist might be perceived to have an expiration date. Nashville, on the other hand, doesn’t seem to worry so much about the idea of “aging out.” Playing music there feels like a way of life, not something you’d age out of. Willie Nelson said it best, “the life I love is making music with my friends” and that doesn’t have an expiration date. No one’s asking Willie if he’s gonna do something else. Or Gillian Welch if maybe she’s thought about dyeing her hair to, you know, be more marketable. (Not that there aren’t parts of Nashville that are just that surface-obsessed and shallow; but that wasn’t the piece I was going for. And those people are in most cities.)
In my dreams, I’ll still be sitting in song circles with people whose songs I love when I’m in my 60’s and 70’s. We’ll still be gathering to sing John Prine or Tom Petty or Lucinda Williams songs. Maybe we’ll still even rent the theater a time or two a year. Get gussied up and out of the house. Point is: music, like creativity, feels like something that I hope to make inextricable from my life.
Eventually, the Nashville window evaporated for me and my family for a whole bunch of reasons I won’t bother you with today. The important part is: I made peace with the beautiful music community I’m part of in Utah and, since making that peace, have done my best to try to “be the change I want to see in the music scene.” It takes work. And I’ve loved it.
Got sidetracked there. Back to aging artists. The famous ones.
So many artists start hot. A simple Google search for “greatest debut albums of all time” will show you plenty of evidence. The Sex Pistols. The Ramones. Jeff Buckley. Guns N Roses. The Band. Billie Eilish.
What's markedly more difficult to find is an artist whose best album is deeper in their catalog. And I don't mean 2-3 albums in. That happens a lot. What I mean is, like, 20 years.3
Let’s look, for just one example, at the inarguably great and legendary Paul Simon.
Setting aside the apartheid-boycott-breaking controversy and the accusations of both cultural appropriation and inadequately crediting his collaborators4, Graceland is, for most fans, the apex for Paul Simon. Yes, Simon & Garfunkel were huge and iconic and had mega-hits, but Graceland has the cultural and critical and commercial bona fides. Disagree? Comment away. But we’re moving forward with that premise.
”PAUL!”
Fine. Let’s go there. Take Simon & Garfunkel’s gigantic hit “The Sound of Silence.” It’s beautiful and haunting and culturally inevitable as all get out, but it’s also just the top of a heap of 60’s folks songs with clever/wordplay titles. It has some very, very good lyric-writing in there, but it also has “‘Fools,’ said I, ‘you do not know. Silence like a cancer grows’” with its first-year Poetry major syntax dragging it down. (Hey, I’m a massive Neil Young fan. I’m quite familiar with the My Artist Actually Trotted Out Some Garbage principle. I promise: it’s best just to accept it and move on.) As song titles go, “The Sound of Silence” is the Jordan Peterson (a dumb person’s smart person) of song titles: it’s a person-who-doesn’t-read-poetry’s idea of a poetry. “The Wet of Dryness!” “The Light of Darkness!” It’s pretty Freshman Year poetry class. (And I like it5! Just, like I said, accepting it for what it is. Shine up the guillotine, if you must.)
So again, let’s set aside Graceland, which absolutely fits my criteria today with its 1986 release being 20+ years after he hit the scene, because it’s time to talk about the high quality of even-later-era Paul Simon.
While not as commercially successful, Rhythm of the Saints (1990, 49 years old) is an artistic triumph. “The Obvious Child” is one of his best songs—take away the Brazilian drums and it’s “Cecilia’s Cousin” but with better lyrics. Or take the bridge at the 2:50 mark of “The Cool, Cool River”; it’s one of the best things Simon’s ever done musically—the quiet build, the horn stabs when he hits the word “heaven”, the emotional vocal especially when his voice breaks just a bit on the word “SOMETI-I-I-MES!” The melody on “Spirit Voices” always gets me, particularly the “ooh-wah, ooh-wah” part. It also makes a case for Simon’s restless creative curiosity, searching the globe6 for new inspiration.
You’re The One (2000, 59 years old) has a handful of Simon songs (the title track, “Darling Lorraine”, “That’s Where I Belong”, “Senorita with a Necklace of Tears”, “Hurricane Eye”) that I think are up there—musically, lyrically, if admittedly not as in-the-epicenter-of-the-zeitgeist—as anything he’s written. The story of arc of “Darling Lorraine” alone is an Oscar bait movie waiting to happen. Somebody get Reese Witherspoon to buy the movie rights.
Surprise (2006, 65 years old) is a little uneven, sure, but so is Hearts And Bones (sue me, but... “Cars Are Cars”? Not Simon’s finest hour). Anyone who’s trying stuff out is gonna have some misses. The best home run hitters strike out plenty. And still we love that they swing for the fences.
So Beautiful or So What (2011, 70 years old) is an album I owe to my friend songwriter (and doctor) Dominic Moore, who told me not to sleep on it— “Dazzling Blue”, “Love and Hard Times”, and my favorite “Rewrite.” The lines from “The Afterlife” are so good: “It seems like our fate/To suffer and wait for the knowledge we seek” COME ON. That’s a guy facing down mortality with a few miles an hour left on his pitches7.
Stranger to Stranger (2016, 75 years old). I’m not saying this to be sensationalist or attention-getting or whatever. But here goes: “Wristband” is one of my favorite and one of the best Paul Simon songs. Great storytelling. A solid groove. A real hook. And a twist in the last verse. No baseball reference needed to convey its greatness.
Oh, you thought I didn’t have a playlist to back up my big Later Era Paul Simon assertions here?
Most artists in their third act spend an inordinate amount of time coasting on the fumes of their first and second acts, recycling the bits that made them beloved, doing whatever it takes to jog the memories of their fans, “Remember how great I was? REMEMBER?!?” The fans end up getting this thing—music—that resembles the beloved thing, but with more Botox, shiny shirts, the makings of a gut, and some more phoned-in lines8. Sometimes they don’t even veil it and turn into sad jukeboxes or Rod Stewart Sings The Standards9 type stuff.
Which is why I save sacred space in my heart and ears for artists who refuse to just ride the nostalgia train/cashcow to their grave, and who somehow stay creatively engaged and vital. That’s not to say they’re still cranking out hits by the dozen; most aren’t. Sometimes they whiff and whiff hard. But they’re defying the gravity that lands other legends in a slow-rotting rut of What Once Was. You see more of the hit recyclers—the Rod Stewarts and so on—than you do of the restless creatives.
Give me the artist who refuses to cash in the chips. The one still taking chances, chasing muses, trying things out.
Paul Simon is just one example of what I call The Restless Creative Club. The club's membership10 is rock solid—Davids Bowie & Byrne, Leonard Cohen, Bob Dylan, Bonnie Raitt, Bjork, Elvis Costello, Neil Young (my favorite and, perhaps, the most uneven11 of them all, even in his prime), and more...all artists who could have just rested on the laurels and royalties of their respective catalogs, but instead dug down to try to find something else (with varied results, yes, but better than being the band that finally relents and releases a “back-to-form” album that is basically a lesser soundalike of your most popular work).
It takes vision and backbone to keep pushing yourself artistically and risking failure, especially when you know you already have a massive, loyal, moneyed audience that would be more than happy to plunk down large sums of money just to hear you play “Bridge Over Troubled Water” until your dying breath. And when that dying breath hits, in your honor and in your memory, they would turn on… “Bridge Over Troubled Water.”
“How Much Is That Doggie In The Window” was actually released in 1952, but I think the song is a good illustration of the contrast between what Music For Kids was and what it became. Besides, it takes a couple years for tech—in this case the bedroom record player—to really catch on.
Can you name these bands? Are they the same band? Are they even bands at all? Do they share a stylist?
My candidates for later-period albums that could at least be ARGUED (keyword there! I’m not saying these are definitively the best albums by these artists; just that an argument could be credibly made) are the best in a band’s catalog. Not surprisingly, the majority of these are bands that were never commercially huge, which allowed them the “luxury” of doing whatever they wanted over their careers rather than trying to replicate whatever luck caused them to sell millions of records:
Time Out of Mind — Bob Dylan
Mule Variations — Tom Waits
American Recordings — Johnny Cash
The Long Surrender — Over The Rhine
Double Negative — Low
Wildflowers — Tom Petty
Skeleton Tree/Dig! Lazarus! Dig! — Nick Cave
Don’t Give Up On Me — Solomon Burke
Raising Sand — Robert Plant/Alison Krauss
Luck of the Draw — Bonnie Raitt
Ray of Light/Music — Madonna
Civilians — Joe Henry
Rumors — Fleetwood Mac(cheating a bit, since the personnel was drastically different but it was a dozen albums into their discography)
Fair & Square — John Prine
Bad Love — Randy Newman
Google “Los Lobos Paul Simon credit” for starters.
Big Paul Simon fan here. I saw Simon & Dylan sing a duet of “The Sound of Silence” about 20 years ago and it still gives me chills. (You can love something and still see its flaws!) If you’ll keep reading, you’ll find that I’m about to talk about how great some of his less-heralded albums are!
Appropriation? Well, maybe. Let’s talk about it later.
Two paragraphs. Two baseball references. Getting awfully jock-y in here. But baseball season just started, so it should be forgivable.
One of my favorite parts of Bono’s book was the part about him and Cillian Murphy sitting in a pub one night and, a few drinks in, Murphy gets up the courage to ask him why his lyrics aren’t as good anymore. Murphy quotes some of the really good stuff to him to which Bono, for once, has nothing to say.
Honestly, late-era Rod Stewart makes it almost impossible to believe that he was ever in the conversation of Best Rock Singers Ever. But he was, in his rock heyday with the Faces and as a solo artist. Now he’s just a recycling bin with fancy hair.
Staying relevant and curious deep into a music career is rare. These aren’t Arguably Best Albums In Catalog, but still very, very good:
Blackstar — David Bowie
Vulnicura/Fossora — Bjork
You Want It Darker — Leonard Cohen
All You Can’t Leave Behind — U2
You Are Not Alone— Mavis Staples
Volume I — Traveling Wilburys
Back On Top — Van Morrison
Van Lear Rose- Loretta Lynn
Chaos & Creation/Flaming Pie/NEW — Paul McCartney
Brutal Youth/The Delivery Man — Elvis Costello
Mystery Girl — Roy Orbison
WARM — Jeff Tweedy
Ode To Joy/Cruel Country — Wilco
Wrecking Ball — Emmylou Harris
The Wind — Warren Zevon
Dirt Farmer — Levon Helm
Teatro — Willie Nelson
Modern Times/Love & Theft—Bob Dylan
Songs From The West Coast — Elton John
If I Could Only Fly — Merle Haggard
I’ve Got My Own Hell To Raise — Bettye LaVette
Silver & Gold/Sleeps With Angels/Mirror Ball/Harvest Moon/Freedom — Neil Young
The Rising — Bruce Springsteen
So Beautiful or So What — Paul Simon
American Utopia/Grown Backwards — David Byrne
His abysmal post-9/11 album Are You Passionate was so bad that it was the first Neil Young album I ever turned in for store credit at a used CD store. It was a lightswitch moment for me, finally realizing that fandom doesn’t mean defending every move by an artist. And thank goodness.
That "Cool, Cool River" bridge is sublime. It's funny that the version of "Sound of Silence" by Paul Simon and Bob Dylan gave you the chills; my thought, when I saw them together in San Diego 1999, was, "Dylan is my hero, but he's the world's worst Garfunkel."