The 5 Best Sheryl Crow Songs That Aren't All I Wanna Do Or Soak Up The Sun

Sheryl Crow's good-time party songs are advertisements for high vibes and easy living, but they're just the commercialized tip of the iceberg for what this landmark talent is capable of. You may have cut your teeth on radio-friendly treats like Crow's highest-charting single, 1994's "All I Wanna Do," and the summer-friendly bouncer "Soak Up the Sun," but a deep dive into Crow's striking catalog reveals tunes with greater meaning and superior musicianship. 

Having tackled genres from Memphis soul to contemporary country, Crow is at her finest when she lets her rootsy layers show through a polished melody with clever lyrics delivering meaningful sentiment. Even with her lesser-appreciated tunes, Crow is a singer-songwriter who rarely misses when it comes to delivering quality music. We had a field day shuffling through the back catalog for the 2023 Rock & Roll Hall of Fame inductee to select our favorite works, an introspective mix of tempos and timbers that show off her skills in a variety of musical modes.

With the solemn soulfulness of "Detours" side-by-side with the crackly punkish energy of "If It Makes You Happy" and the gorgeous pop balladry of "Always On Your Side," we think Crow's best songs are a hodgepodge of sounds that demonstrate the depth and breadth of this singer-songwriter's singular talent.

Crow takes her well-known slacker anthem leanings in a slightly different direction with "If It Makes You Happy," a crispy three-chords-and-the-truth rocker from her self-titled second album that's not afraid to admit its own darkness. Rather than celebrating the sunnier side of having it hard, the singer-songwriter describes a rock-bottom co-dependency scenario where the only way out may be through. "Scrape the mold off the bread / bring you comics in bed / and make you French toast again," she sings in a guttural drone, as if the monotony of her situation isn't going to stop her from going through the motions. She and the subject she's singing to are going to be sticking around in the muck a while, it seems, as they figure out how to rise above.

But if it's a Sheryl Crow song, you know she'll make the best of a bad situation, and sing about it as she does. "If it makes you happy / It can't be that bad," she wails in the chorus, "If it makes you happy / then why the hell are you so sad?" Modern philosophy has seldom cut to the heart of sorrow so cleanly. It's another classic Crow combination of ennui and elation, her trademark blend of real-world honest and better-life aspirations that makes so many of her works modern life anthems. She reminds everyone who hears her that everything can be overcome eventually — "So what if right now everything's wrong?"

Crow takes the long and winding road to a Beatle-esque ballad that tests her higher vocal range and breaks down the strong persona, revealing a kernel of aching authenticity. Cosmic longing for understanding and a peaceful place to simply be guide the lyrics into spiritual semi-psychedelia. "Here we are / Burning faster than the closest star," she sings gently, "Falling back down to the Earth / I love you so / It sometimes hurts" If fans picked up the "Wildflower" album to party hearty like Crow had encouraged in the past, they quickly learned that she was more than songs about day-drinking and beachcombing in the midst of life's greatest trials. This song proved her artistry as a clear-eyed philosopher who knows when to dial back the good times and face reality.

Crow composed this gentle tune for cyclist Lance Armstrong, her boyfriend at the time, and the influence of his children's ability to find sweetness in the middle of a world that tends to crush the tender things. The message that love, like wildflowers, can appear even in the most unwelcoming of spaces, is pure and clear, uncluttered by Crow's usual canny observations about the grittier aspects of life. It's a beacon for anyone who meditates on the lyrics while floating on the lovely waves of her angelic head-voice vocals.

It may not count as one of the songs Sheryl Crow wrote for other artists, but a guest appearance by the legendary Sting makes "Always on Your Side" feel like a premium collab regardless. The former Police singer lends his reedy vocals to the Apple iTunes edit, giving Crow a cohort in a heartbreaking piano-based ballad about letting go. It has no aspirations higher than making us all cry, and it comes through with flying, weeping colors. Crow extrapolates a bit of Elton John's classic "Someone Saved My Life Tonight" in the line, "Butterflies are free to fly, and so they fly away," then takes the cracking emotion three steps further: "And I'm left to carry on and wonder why / Even through it all, I'm always on your side." The sober maturity of the imagery and the unadorned vocals deliver on the gut-wrenching sadness, showing how restrained Crow can be when it suits the mood.

A solo version on Crow's wonderful 2005 "Wildflower" album feels even more raw and honest, stripped back to a simpler piano-based arrangement. It's a poignant performance that reveals the sadness of the lyrics even better than the duet version, laying all the sorrow on Crow's capable shoulders. This is one of those soundtrack-ready songs that can easily strike you in the heart just when you least expect it, whether you've heard it a thousand times before or you're just now making the discovery.

"Detours" is a two-stepping philosophical musing on lost love, showcasing a deceptively bouncy backbeat for a tune about being vulnerable. Flutes and vocalized "na-nas" in the distance add a delicate layer of playfulness while Crow begs for guidance, praying "Mother, teach me to love with a paper-thin heart." The simple melodic catchiness defies her usual rock-blues bombast and stays firmly in bluegrass-pop territory, which suits Crow's gentler vocal delivery beautifully. It's a mode she explores less often than her other formats, but one that deserves equal attention for its careful delivery and artful flourishes.

This winner is the title track from Crow's 2008 album "Detours," her first work after a particularly difficult stretch, which included her public break-up from banned-for-life former pro-cyclist Lance Armstrong and her diagnosis and treatment for breast cancer. The subject matter in many of the songs is even more personal than her past pieces; "Make it Go Away (Radiation Song)" in particular takes listeners into her head and heart during her treatments. But "Detours" is a stand-out amongst the other introspective explorations, one in which Crow seems to be starting over from scratch but remains ready to embrace life.

Crow cuts looser than usual with a jingly stomp-and-clap sing-along that simplifies her formula into a playful minimalist framework. This is one of those songs that's easy to forget about until it pops up on a summer vibes playlist or on the sound system in the grocery store. Suddenly, your head is bopping and your toes are tapping, and you're vocalizing to the sweet hippie-dippy message that might as well be on a tie-dyed T-shirt. It's another tune from her excellent "Detours" album, one that reads like a humble realization about what's really important in life, a soulful uplift delivered in a hammock swing of a rhythm.

There's a more serious impetus for the lightness of the song, however. Crow was inspired by the strength of Hurricane Katrina victims and the perseverance of the New Orleans residents who refused to abandon their beloved city in the wake of such destruction. Following verses that describe how powerless we feeble humans are against the whims of life, a chorus full of sunshine reminds everyone of one immutable fact: "Oh, everybody / Devil take your money / But money's got no hold on me / 'Cause oh, oh, everybody's makin' love /'Cause love is free." Who couldn't benefit from a reminder like that?