Our Annual Grandparents’ Guide to Today’s Pop Artists

A grandfather listens to music with his granddaughter. They are in a room lined with CDs and books, and guitar is in the foreground.

(Image credit: Getty Images)

Did you take your grandkid to see A Complete Unknown? You want the youngsters to understand your music, of course. But did your grandkid take you to see Sabrina Carpenter? Maybe not. Maybe too embarrassing — for them or for you.

We can’t help you with that. But we can at least help you understand what’s going on in pop music and tip you off to some newer artists that your grandkids might not even know about. What we’re looking for is common ground, bridges, new music that speaks to you and speaks to the younger generations. So here are three current artists that fit that bill.

And as always, we stress that it’s not about soundalikes, but about artists with kindred sensibilities and creative drives. Listen to the playlist at the end of this article. You may find some of these comparisons a stretch. That’s okay. We want you to stretch, to be open, to find new horizons and embrace the sounds.

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If you like Bob Dylan… try Jesse Welles

Even before A Complete Unknown put new focus on Dylan’s early 1960s years in the Greenwich Village folk scene, this tousled-hair kid was turning up on TikTok and YouTube — the Washington Square of our era? — with poignant and often witty ditties about the world he sees around him. “War Isn’t Murder,” he sang with pointed sarcasm. “Pain can change a person into something you don’t know,” he sang in his working-class lament, “Golden Age.” Often appearing in a work shirt or jean jacket, performing outside in his native Arkansas, he’s not the least bit afraid to challenge your viewpoint, whatever it is. Nor is he afraid of comparisons. He even did a version of Dylan’s “Don’t Think Twice, It’s All Right” last year. And he’s prolific. In March, he released the album Between the Power Lines, collecting 65 of these in-the-moment performances made in just a five-month period last year.

While Welles continues to tackle the topical (in “LA Fires,” which came just days after those fires broke out, he questioned both the theories that came while the city was still aflame and what some saw as a lack of effective response in fighting the fires), he doesn’t want to be pigeonholed as a protest singer. Sound like anyone else we know?

“Time is not a mirror,” he sings in “That Can’t Be Right,” “It’s some distorted view, of the way you thought you was and what you thought they thought of you.” On his new studio album Middle, he has moved somewhat away from the headlines and more to the heart.

With that album he’s crafted his own folk-rooted sound, with fuller but still spare production. Still it’s hard not to think of Dylan when hearing the violin that spikes the new album’s opening track, “Horses,” which could have come straight from Scarlet Rivera on the Rolling Thunder Revue tour. And a recent video for the new song “Why Don’t You Love Me” is full-on Jesse Goes Electric. Welles is practically daring us not to think of Dylan. But then, has Dylan ever sprinkled Star Wars references through his songs as Welles is known to do? Didn’t think so.

If you like Neil Young… try Big Thief

This hauntingly atmospheric Americana of Big Thief — currently a trio of singer-guitarists Adrianne Lenker and Buck Meek and drummer-producer James Krivchenia — is hard to pin down, even as it has built an impressive, steadily-growing audience in recent years. There’s a little of the low-key end of Fleetwood Mac in the earthy singing and painterly arrangements. There’s a little Leonard Cohen in the direct melodies and layered poetry weaving through the songs. There’s even a little Tori Amos in Lenker’s deeply self-probing lyrics and at-times imaginatively quirky music, especially in her solo releases that have come parallel to the group’s albums.

So why settle on Neil Young? Well, like him, Big Thief moves freely through all of those sounds and styles at the service of open, sometimes raw expression, a mix of sophisticated musical versatility (both Lenker and Meek went to the Berklee School of Music) and emotional vulnerability. Think particularly of Young’s 1972 classic Harvest, but also of his darker albums that followed that success, including Tonight’s the Night and Rust Never Sleeps.

“Love, Love, Love,” from the most recent album Dragon New Warm Mountain I Believe In You (which was nominated for the Best Alternative Music Album Grammy Award), has Young’s Crazy Horse edge, showing off Meek’s love of wild, distorted guitar that first appeared on the band’s debut, Masterpiece, before the band was as distinctive as it has become. But the same album’s “Promise is a Pendulum” is somehow both somber and yearning. The key ingredient throughout, though, is intimacy. “I want to be the shoelace that you tie,” Lenker sings in “Blue Lightning.”

And if you really want to explore the intimacy, and maybe have a good cry while at it, check out Lenker’s 2024 album Bright Future, which got a Best Folk Album Grammy nomination. If the ode to her mother, “Real House,” doesn’t get to you, nothing will. And with the song “Sadness As a Gift,” contemplating a relationship that didn’t work out, she seems strangely cheered, which is a good summary of her and Big Thief’s art.

If you like John Coltrane… try Lakecia Benjamin

“We are celebrating joy tonight, we are celebrating love and light and unity and peace and power and freedom for everybody,” ascending New York sax star Benjamin preaches, with exuberant spirit, at the start of her latest album, 2024’s Grammy nominated Phoenix Reimagined (Live). This is the spirit of someone who has been through a lot, notably a serious 2021 car crash, with a broken jaw among her injuries. She basically had to re-learn to play. But she also came through with a buoyant embrace of life, hence the title of this album, and its studio predecessor, Phoenix. Anyone who’s seen her perform has felt that enthusiastic energy radiating from her.

It also brought a new dimension to her music. Her Coltrane love is never far from the surface — Phoenix Reimagined kicks off with her original, “Trane.” And in 2020 she released Pursuance: The Coltranes, featuring interpretations of works by both John Coltrane and his wife, the innovative jazz-world-spiritual composer-musician Alice Coltrane. And any jazz fan would clearly hear Coltrane’s presence in her fierce, fluid, dense modal soloing.

But she’s no Coltrane imitator. For one thing, some of her pieces feature singing, rapping and spoken word — some by her, some by guests including veteran singing star Dianne Reeves (on the elegant “Mercy”) and activist Angela Davis (the searing “Amerikkan Skin”). Elsewhere, elite guests include guitarist John Scofield, keyboardist Patrice Rushen and sax giant Wayne Shorter (a spoken-word bit on the Phoenix track “Supernova”).

In addition to Coltrane’s presence, Benjamin carries the depth and power imparted from key mentors including trumpeter Clark Terry, sax player Gary Bartz and drummer Terri Lyne Carrington, who produced the Phoenix album. At times, such as on the bright-toned song “Let Go,” she moves toward soul-jazz melodics. Other times, such as the Phoenix Reimagined title track, on which she’s joined by Scofield, pianist Jeff “Tain” Watts and trumpeter Randy Brecker, she pushes fiercely into pure fire. And yes, on the live session she does “My Favorite Things,” which Coltrane turned into a modern jazz standard. But like her idol, she plays it her own way, celebrating joy, love, light and freedom.

Easy listening

We compiled a playlist and set it up on Spotify: https://spoti.fi/3EbzrFn.

Jesse Welles:

“War Isn’t Murder”

“That Can’t Be Right”

“Golden Age”*

“Horses” from Middle

“Why Don’t You Love Me”

Big Thief/Adrianne Lenker:

“Blue Lightning” from Dragon New Warm Mountain I Believe In You

“Promise is a Pendulum” from Dragon New Warm Mountain I Believe In You

“Love, Love, Love” from Dragon New Warm Mountain I Believe In You

“Real House” from Adrianne Lenker’s Bright Future

“Sadness As a Gift” from Adrianne Lenker’s Bright Future

Lakecia Benjamin:

“Intro/Trane” from Phoenix Reimagined (Live)

“Amerikkan Skin (featuring Angela Davis)” from Phoenix

“Let Go” from Phoenix Reimagined (Live)

“Phoenix Reimagined” from Phoenix Reimagined (Live)

“Liberia (featuring Gary Bartz)” from Pursuance: The Coltranes

* As of this writing, “Golden Age” was not available on Spotify, but you can find it on YouTube.

Note: This item first appeared in Kiplinger Retirement Report, our popular monthly periodical that covers key concerns of affluent older Americans who are retired or preparing for retirement. Subscribe for retirement advice that’s right on the money.

Steve Hochman has covered popular music at the Los Angeles Times, Rolling Stone, Billboard and Variety as well as serving as music critic for public radio shows on KPCC Los Angeles and KQED San Francisco. He’s a co-author of the recent Melissa Etheridge graphic biography, Heartstrings, and has written liner notes for a wide range of album releases. Currently he is a lead writer for Spin magazine, New Orleans’ OffBeat and the Bluegrass Situation.