A Dozen Deep Songs About Caring and Connecting

from our Optimisticles blog series

By Wes Kilgore, Well Beings

Caregiving doesn’t come with a soundtrack, but maybe it should. Whether you’re showing up for someone day after day, navigating a loved one’s diagnosis, or just trying to remain steady amid the chaos, music has a sneaky way of holding space for all those big, complicated feelings. The songs below aren’t just about love — they’re about showing up, sometimes in silence, sometimes in grief, and sometimes with messy, unwavering devotion. From quiet ballads to rock anthems, these twelve tracks tap into what caregiving feels like: hard, hopeful, heartbreaking — and often, kind of beautiful.

Ray LaMontagne – I Still Care for You

In 2004, Ray LaMontagne burst upon the singer/songwriter scene with the bluesy/folksy album and title track Trouble, but it was his 2008 album Gossip in the Grain and this track in particular that caused me to stand up and really take notice. I’m a sucker for a psychedelic-tinged, off-kilter drum fill, and I Still Care for You is chock full of them. The song is a hushed, aching ballad — it doesn’t shout, but it lingers.
LaMontagne is famously taciturn, rarely commenting on what his songs are “about.” But its stark lyrics and raw delivery evoke a vow of enduring compassion for someone despite past pain.

• What Critics Said: Many reviews called it “ethereal” — a word that actually fits. It’s grief and grace, distilled.
• Behind the Mic: LaMontagne said Gossip in the Grain was his moment to open up more, and “not be quite so reserved” in his songwriting.
• On Screen: The song made it into an episode of House, in which a man suffering from chronic, unexplained pain attempts suicide. The song’s haunting melody plays during the closing scene and perfectly underscores the episode’s poignant themes of empathy, resilience, and the enduring human spirit in the face of suffering.

Bill Withers – Lean on Me

As a nascent musician, I often referred to Bill Withers as my Spirit Animal. There was something about the way that his insightful, sincere, and lean body of work sat uniquely at the nexus of R&B, funk, and folk that spoke volumes to me. Withers wrote Lean on Me based on his childhood in the coal mining town of Slab Fork, West Virginia — a place where neighbors showed up for each other without being asked.
He wanted to capture that kind of everyday kindness, and he did, with a simple Wurlitzer piano and lyrics that feel like advice from an old friend. In a SongFacts interview, he recalls a stranger helping him once after he blew out a tire on a country road. Moments like that are at the heart of the song.

• Why It Endures: Its gospel-tinged melody and plain-spoken, sing-songy lyrics make the message relatable and easy to sing along with – a deliberate choice by Withers, who believed in the power of simplicity.
• Bill’s Words: “I have no idea where it came from… It just came, all of a sudden,” Withers said about writing the song, noting that the phrase “lean on me” felt like a natural conclusion to the feeling he was trying to express​.
• Fun Fact: Released in 1972, Lean on Me was Withers’ first and only #1 hit song. Unusually, it hit #1 again in 1987 with a club-style cover by Club Nouveau, making it one of the rare songs to top the charts with two separate versions.

The Jackson Five – I’ll Be There

Not to date myself too much, but my very first concert was The Jackson 5 at the Hampton Coliseum in nineteen seventy… (cough, cough). My family was huge Jackson 5 fans, and we’d practice their dance moves and songs for hours (I was Jermaine). My affinity for the group was thanks in no small part to I’ll Be There. With Michael and Jermaine trading lead vocals, the powerful message of the song wasn’t lost to my young ears — assuring a loved one that “just call my name and I’ll be there” through all of life’s ups and downs. Michael was just 11 when they recorded this — and somehow, it’s one of the most emotionally mature tracks of the Motown era.

• Michael’s Take: In his 1988 memoir, Moonwalk, he said this song proved the Jackson 5 were more than just bubblegum pop.
• Record Breaker: Released in 1970, it replaced I Heard It Through the Grapevine (Marvin Gaye) as Motown’s most successful single released in the US. It held that record until the release of the Lionel Richie/Diana Ross duet Endless Love in 1981.
• Fun Fact: I’ll Be There became the fourth consecutive #1 single for the Jackson 5, making them the first group to have their first four singles top the charts.

The Pretenders – I‘ll Stand By You

I’ll Stand By You might just be the ultimate ride-or-die anthem. Chrissie Hynde co-wrote it with powerhouse hitmakers Tom Kelly and Billy Steinberg, adding that she was “embarrassed” by attempting to aim for something radio-friendly and full of heart. Regardless, she nailed it. The lyrics pledge unwavering comfort to a loved one in times of darkness – a theme reflected in the music video, which depicts Hynde caring for a sick man in a hut.

• In Her Own Words: Hynde once said the song was a “cold-blooded” attempt at writing a hit, but even she was surprised by how much it resonated.
• Fun Bit of Music Lore: Noel Gallagher from Oasis once told her he wished he’d written it. That’s high praise from a rock star who is notoriously quick with a snide comment.
• Legacy: It became The Pretenders’ biggest pop hit, reaching the Top 20 in the US and UK in 1994​ — and it’s been covered for charity campaigns, child welfare PSAs, you name it.

Simon & Garfunkel – Bridge Over Troubled Water

One of the most performed songs of the 20th century, Paul Simon was inspired to write Bridge Over Troubled Water by a gospel lyric and wrote it almost instinctively. “I have no idea where it came from… It just came, all of a sudden,” Simon said, marveling at how the song flowed through him as if by grace. He handed the lead vocals off to Art Garfunkel because, in his words, “Only Artie’s voice could do it justice.” The result was a soaring ballad that offers steadfast comfort to a friend: “When you’re weary, feeling small… I will lay me down.”

• Legacy: It spent six weeks at #1 in the U.S. Won a gazillion Grammys. Inspired a thousand covers. Gave people something to hold on to.
• Little Detail: “Sail on, silver girl” was a wink to Simon’s wife’s first gray hairs.
• Big Impact: It has established itself as one of the go-to songs for crises and funerals, and is a modern hymn for anyone going through it.

Foo Fighters – My Hero

There goes my hero… but he’s ordinary. That’s the point. Dave Grohl wrote this as a tribute to the unsung heroes. Everyday people — not rock stars, not icons, just the ones who show up when you need them most.

• COVID Era Flashback: In 2020, My Hero took on new resonance as an anthem for healthcare workers. Dave Grohl performed an acoustic rendition from his home dedicated to doctors and nurses, saying, “Here’s to all the heroes” in our communities​.
• Clarification: Grohl was a bit uncomfortable with fans assuming it was a Kurt Cobain memorial, saying “there’s definitely an element of Kurt in that song,” but emphasizing that its true spirit was broader, praising the quiet heroism of everyday folks.
• Fun Fact: The song’s music video shows a faceless hero rescuing a baby and a dog from a burning building, but it never reveals the protagonist — emphasizing that heroes are defined by actions, not fame.

The Beatles – When I’m Sixty-Four

This one’s pure charm. When I’m Sixty-Four is Paul McCartney having a little fun — imagining what it might be like to grow old with someone and still make each other tea, knit sweaters, and rent a cottage near the Isle of Wight. It’s whimsical, for sure, but underneath the music-hall bounce and the clarinet flourishes is a real question: Will you still love me when I’m not so young and shiny anymore?

Paul wrote the melody as a teenager, fiddling around on the family piano in Liverpool. He later joked he thought he was writing something Sinatra might sing — a cheeky nod to his affinity for old-school crooning and vaudeville styles.

• Early Days: Back in the Beatles’ Cavern Club era, Paul would break out the tune when the amps cut out. It didn’t even have lyrics yet — just him and a piano keeping the show rolling.
• Lyrical Gold: John Lennon helped fill in some of the sweet silliness, like “grandchildren on your knee: Vera, Chuck and Dave.” That kind of detail makes it stick.
• Behind the Scenes: The Beatles recorded this first for Sgt. Pepper’s. They even sped up Paul’s vocals in the studio to make him sound younger — a little sprightlier for the role.
• Full-Circle Moment: In 2006, when McCartney actually turned 64, he joked he never expected to still be singing it. And yet, fans did still need him (and some probably wanted to feed him too).

Peter Gabriel & Kate Bush – Don’t Give Up

Released in 1986, this powerful duet about perseverance in hard times delivers a gut-punch with a velvet glove. Peter Gabriel was reflecting on the “heavy psychic toll” of joblessness and despair in Thatcher-era Britain when he wrote it. He conceived a song about a couple facing financial hardship, with the man voicing anguish and the woman responding with comfort. Pairing his vulnerability with Kate Bush’s preternatural calm, they sing as two halves of one story — one falling apart, and one trying to hold it all together.

• Inspiration: Gabriel said the initial spark came from seeing Dorothea Lange’s Depression-era photos and not being able to shake them.
• Almost a Different Story: He originally asked Dolly Parton to duet (!). She passed. We got Kate Bush instead. No complaints.
• Enduring Impact: Elton John says this song literally “saved my life” by inspiring him to overcome addiction. And the song was so important to late Friends star Matthew Perry that his family played it at his funeral​.

Taylor Swift ft. The Chicks – Soon You’ll Get Better

On her 2019 album Lover, Taylor Swift hit pause on her preoccupation with forensically analyzing relationships with her exes to pen Soon You’ll Get Better, a deeply personal, moving song about her mom’s battle with cancer. She described it as the hardest song she’s ever written, explaining that including it on the album was a “family decision.” The raw lyrics describe hospital visits, prayer in the face of doubt, and a child’s desperation to comfort her mom, making it one of Swift’s most vulnerable compositions.

• Taylor Said It Best: “I can’t sing it. It’s hard to emotionally deal with that song,” Swift admitted in a live webcast before the album’s release. Consequently, she’s only performed it live once — during a livestream for frontline healthcare workers in 2020.
• Collab Note: The song’s soaring, beautiful harmonies are courtesy of The Chicks (formerly The Dixie Chicks), a band she grew up idolizing. Swift says that The Chicks were “the band that made me wanna do this.”​
• Underappreciated: The song peaked at #63 in the U.S., but it marked The Chicks’ first appearance on the country charts in 13 years.

Elvis Costello – Veronica

This one sneaks up on you. Its bright and upbeat vibe belies the poignant story hiding within it. It’s actually about Elvis Costello’s grandmother, Mabel (her confirmation name was Veronica) who lived with Alzheimer’s disease. Co-written with Paul McCartney, the lyrics imagine her moments of clarity and fading memory, balancing nostalgia with reality.

• Why It Matters: In a VH1 interview, Costello reminisced about his grandmother’s “terrifying moments of lucidity” in the midst of her dementia, and how that fueled the song’s narrative​. These flashes where Veronica briefly recognizes her reality were heartbreaking and inspired Costello to honor her experience in song.
• Beginning of a Beautiful Friendship: Veronica was one of the first songs that Costello and Paul McCartney wrote together. McCartney not only co-wrote it but he also plays his signature Höfner bass on the recording​. They went on to collaborate on more than a dozen tunes.
• Big in America: It became Elvis Costello’s highest-charting single in the U.S., reaching #19 on the Billboard Hot 100​ and earning him MTV’s Best Male Video award in 1989. The song’s popularity brought memory loss into the pop spotlight in a way that few songs had before.

Donny Hathaway – He Ain’t Heavy, He’s My Brother

Originally made famous by The Hollies in 1969, Donny Hathaway turned He Ain’t Heavy, He’s My Brother into something more deeply soulful and spiritual in 1971. Hathaway possessed a voice so rich and emotive that it inspired Stevie Wonder to emulate him. His slower, richer, almost gospel sermon-like vocals were the perfect vehicle for the track, which is essentially about carrying someone else’s burden, without question.

• Background: The title came from Father Edward Flanagan’s Boys Town, a home for orphans. The phrase “He ain’t heavy, he’s my brother” has been an inspirational motto since the 1940s, used to illustrate caring for those in need.
• Heavy Hitters: Hathaway’s version includes King Curtis on sax, who played on Aretha Franklin’s Respect and The Coasters’ Yakety Yak, and Cissy Houston (aka Whitney’s aunt) on background vocals.
• Songwriting Duo: The song was written by Bobby Scott, a multi-instrumentalist and singer who wrote the 1956 hit Chain Gang and was a sideman to Quincy Jones and Chet Baker, and Bob Russell, a lyricist who collaborated with Duke Ellington and Quincy Jones.

Nick Cave & The Bad Seeds – Into My Arms

Released in 1997 on The Boatman’s Call, this tender piano ballad is an unadorned prayer for the safekeeping of a loved one. Ironically, Cave opens the song by professing “I don’t believe in an interventionist God” – before immediately proceeding to pray that his love will be guided into his arms.

• In the Moment: He performed it at his close friend Michael Hutchence’s (INXS) funeral in 1997, but he famously requested the TV cameras be turned off​. Cave wanted the performance to remain intimate and respectful.
• Inspiration: Cave wrote it following the breakup of a long-term relationship and a brief romance with PJ Harvey​. He composed it while in rehab: “I was walking back from church through the fields… the tune came into my head,” he recalled. He hurried to a piano to work out the chords, then “sat on [his] bed and wrote those lyrics” in one go.
• True Intention: Though often described as melancholic, Cave intended the song to convey “melancholic optimism.” Indeed, “Into My Arms” somehow manages to masterfully balance sadness and hope: it’s essentially a love song that says, I have faith in you and in us, even if I have faith in little else.

Are you a caregiver? What are some songs that got you through tough days? Submit your songs and why they made a difference to info@wellbeings.org

About the Author

Wes Kilgore is a writer, musician and bon vivant based in the Washington, DC area, and the proud parent of two disturbingly well-adjusted young women and two borderline sociopathic Corgis.