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1
Both Sides Now (2000)
Released
Joni Mitchell
Hear what happens when Mitchell sings “Both Sides Now” again. The orchestra gives her time to weigh words that moved past more quickly in her earlier recording. The new version closes a sequence that runs from flirtation through disillusionment. “A Case of You,” the other Mitchell song among the standards, gives you a second way to hear what time has done to her phrasing.
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Laughter In Summer (2026)
Released
Beverly Glenn-Copeland
Listen to “Harbour” for what the record makes of memory. Glenn-Copeland wrote it for Elizabeth’s birthday, then found his way back to it through improvisation after memory loss. The album they made together also revisits “Ever New” in a recording at Montreal’s Hotel2Tango. The familiar music is still there, and the two of them make new ways to reach it.
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Older Than My Old Man Now (2012)
Released
Loudon Wainwright III
The title song puts three generations into one recording. Wainwright reads his father’s words, then his son Rufus sings on the track. “I Remember Sex,” with Barry Humphries, finds the joke in a different sort of looking back. The record leaves plenty of room for getting older to be strange and funny.
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The Hard Truth (2026)
Released
Wynonna
“Everything” remembers being in the spotlight at eighteen and learning to look and sound the way people expected. On “Am I Missing Out,” she can still wonder how much life there might be beyond what she knows. Put this on if you want to hear a country singer look back on a long working life and still ask what she might do with the rest of it.
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4:44 (2017)
Released
Jay-Z
On “Family Feud,” Jay-Z asks what older and younger rappers gain by turning on each other. “Legacy” brings the question home. His daughter asks him what a will is, and the track gives him room to think aloud about what a parent passes down. The change in scale from the wider culture to a voice in the family makes the record worth hearing in sequence.
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Last Leaf on the Tree (2024)
Released
Willie Nelson
Nelson sings the Tom Waits and Kathleen Brennan song “Last Leaf” like someone who knows what it costs to be the one still here. His son Micah produced the album, and the two cowrote “Color of Sound.” Hear them together for the way one song measures what’s gone while the other leaves room to imagine a beginning after an ending.
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Seven Psalms (2023)
Released
Paul Simon
Set aside half an hour for this one. Simon made it as seven movements meant to be heard together, with his guitar and voice at the center. By the time Edie Brickell sings with him, the questions about what comes after this life have another voice in the room. Listen when you want to hear someone stay with a question long enough for it to change.
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Negative Capability (2018)
Released
Marianne Faithfull
Faithfull brings “As Tears Go By” back in a voice that sounds as if it knows the people it’s lost. She also returns to “Witches Song,” which has a more incantatory feel here than it did on Broken English. The two tracks let you hear different things a singer can still discover in material she has lived with for years.
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Meu Coco (2021)
Released
Caetano Veloso
“Autoacalanto” grew from listening to his grandson sing himself to sleep. The boy’s father, Tom, plays guitar with Veloso on the track. Elsewhere, “Enzo Gabriel” takes its cue from a popular baby name. Put this on if you want a record that treats grandparenthood as a chance to pay attention to the people and the world arriving after you.
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12 (2023)
Released
Ryuichi Sakamoto
While recuperating, Sakamoto recorded small piano and synthesizer sketches and thought of them as a diary. He kept the dates as track titles, including the entry marked “20220302 – sarabande.” Try a few in sequence. The record makes the changing sound of a few notes feel worth hearing from one day to the next.
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The Boys of Dungeon Lane (2026)
Released
Paul McCartney
“Days We Left Behind” takes McCartney back to the Liverpool streets he knew before the Beatles. The album started in a different spirit. He found a chord he didn’t recognize while playing guitar with producer Andrew Watt, and following it led to “As You Lie There.” That combination of looking back and following an unfamiliar sound is what gives the record its life.
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Heart’s Ease (2020)
Released
Shirley Collins
The traditional song “Wondrous Love” is over in a couple of minutes. “Crowlink,” at the end, opens up a much stranger space. Collins made both fit on a record that gives her familiar folk songs company from new material. It’s a good choice if you want to hear what a singer can still try after decades of working with old songs.
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Blackstar (2016)
Released
David Bowie
Bowie made this late record with saxophonist Donny McCaslin’s jazz quartet at its core. The drums and bass on “’Tis a Pity She Was a Whore” keep moving around a voice that sounds in no hurry to explain itself. Follow it with “Lazarus” for a very different kind of tension. The album makes room for the possibility of an ending and the pleasure of finding a new band.
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Joy’All (2023)
Released
Jenny Lewis
“Puppy and a Truck” begins with the indignities of her forties and makes a good afternoon out of a few modest pleasures. Lewis wrote it for a songwriting workshop hosted by Beck. That detail fits the record. An artist with plenty of songs behind her was still willing to take an assignment and see what it turned into.
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Sad and Beautiful World (2025)
Released
Mavis Staples
On “Satisfied Mind,” Staples sings about the things money can’t buy back, including youth. She also takes on “Human Mind,” a song Hozier and Allison Russell wrote with her in mind. Start with those two if you want to hear how a singer draws on a lifetime of experience and still lets other generations give her something new to sing.
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