5 Sheryl Crow Songs That Prove She Belongs Among Rock's Greats

"Did she not get the credit that she deserved all these many years? No, I don't think she did," Stevie Nicks said of Sheryl Crow to The New York Times in 2022. Even ignoring Crow's nine Grammys out of 32 nominations, 19 songs in the Billboard Hot 100, and 22.6 million records sold, Nicks' statement would be true. There's a timeless, pan-rock quality to Crow's music, one that crosses genres, generations, and listeners' backgrounds to lift her into rock's pantheon, especially her best songs.

It's not an easy task choosing only five Crow songs out of her 12 studio albums. Her music is way more refined and subtly composed than casual listeners might realize, no matter how hummable. It's full of polish elements that speak of immense time, effort, and care in the studio. We've got to choose tracks from her catalogue that demonstrate this core songwriting quality and also the full breadth of Crow's versatility as a rock artist, skewing country, blues, pop — whatever works for any given number. We're also going to stick to tunes that she wrote for herself, rather than those you don't know she wrote for other famous musicians. Finally, we're going to highlight songs that retain the timeless quality we mentioned earlier, regardless of how their production or style might sound couched in a particular period — especially the mid-90s when she came to fame with 1993's "Tuesday Night Music Club." But no matter what Crow era we highlight, these songs prove she belongs amongst rock's greats.

From the opening bongos to the final fade-out, "Everyday Is a Winding Road" from Sheryl Crow's self-titled 1996 album is pretty much a perfectly composed song that belongs on every country rock playlist. It's trim without being reductive, familiar without being formulaic, leans into the chorus without relying on it, wields textures and overlays to build and release tension, adds variety over its length using varying instrumental lines, and on and on. The track is expertly crafted, rootsy, and universal enough in sound and sentiment that pretty much anyone can enjoy it. Really, you could use "Everyday Is a Winding Road" to teach core songwriting to fledgling musicians, especially to illustrate how each band member plays a role that, when fused, produces music greater than the sum of its parts. 

Then there's the song's sentiments, which depict a grounded, upfront, undeluded outlook on life perfectly reflected in the music. There are little lyrical vignettes — windows into everyday life — like, "He's got a daughter he calls Easter / She was born on a Tuesday night," that mirror those found in Crow's breakout hit, "All I Wanna Do": "We are drinking beer at noon on Tuesday / In a bar that faces a giant car wash." We guess Tuesday is as homegrown of a day as there could be.

"Everyday Is a Winding Road" even has a deeply personal meaning for Crow, as the song's name comes from drummer Paul Hester, who quit mid-tour following the release of "Tuesday Night Music Club" because of depression and wound up dying of suicide in 2005. "Songs like that seem to recreate themselves, and in a perfect world bring solace to some people," Crow told American Songwriter.

The more you explore Sheryl Crow's discography, the more you realize that she deserves to be ranked amongst rock's greats. "A Change Would Do You Good" from 1996's self-named album might not be deep-cut status, but it didn't even breach the Billboard Hot 100. That's a very odd fact given the song's quality and Crow's success at the time (though it did appear on other charts). The track even came equipped with a star-studded, highly stylized, and memorable music video. But without such a feature, which critics could argue is a gimmick, "A Change Would Do You Good" sounds exactly like what it is: A tightly written song where every part makes sense, flows from what came before, tells a whole story that's down-to-earth in true country rock and/or roots rock fashion, and has little to dislike.  

Unlike a lot of other Crow songs, we don't have any info about what inspired "A Change Will Do You Good" other than the obvious title and chorus line: "A change would do you good." In the music video, Crow acts as a kind of mischievous fairy sprinkling magic dust on people so they swap places and get a taste of a different life. It's all done in good fun, which is another reason why both this track — and Crow's entire body of work — is worthy of acclaim. 

It would be off-putting if Crow was too self-serious and arguably ruin the accessibility of her music. But even though a song like "A Change Will Do You Good" deals with a real, serious topic, Crow frames it in a way that invites people to listen. She's as versatile as she is sensible, in both music and approach.

During an appearance on "The BobbyCast" in 2026, Sheryl Crow said of "My Favorite Mistake" from 1998's "The Globe Sessions": "It's the only song when it comes on the radio, I don't turn it off. I don't overanalyze it, criticize it, whereas other things I go, 'Gosh, I wish I would have done this or would have done that.'" That's quite a statement considering the obvious craftsmanship that goes into Crow's songwriting. But we share her sentiment: We'll never get tired of hearing "My Favorite Mistake," the same as Crow will never get tired of singing it.

"My Favorite Mistake" works so well because of all the hallmarks of great songwriting, rock or otherwise. It tells a story from the very first line, "I woke up and called this morning / The tone of your voice was a warning," and develops it along with the music. The verse builds the track's core chord progression into a payoff that fully comes together in the outro: "Did you know, could you tell / You were the only one that I ever loved?" Musically savvy listeners can hear how the song is going to develop from the get-go, but it's never too obvious when it does. The whole tune is also very mild, mid-tempo, and radio-friendly, which in the hands of another artist might render it dull. But like always, Crow has a rocky-enough edge to elevate "My Favorite Mistake" well above a self-pitying, whiny breakup track.

Plus, "My Favorite Mistake" hasn't stayed locked to a certain time and person. It's stayed alive and relevant, like the best songs. As Crow told Howard Stern in 2022 (on YouTube), she's had quite a few "favorite mistakes" since releasing the track.

Definitely the silliest of our choices, "Steve McQueen" from 2002's "C'mon, C'mon" might raise some eyebrows precisely for that reason. It invokes visions of bygone Americana in an intentionally on-the-nose way, alludes to Lynyrd Skynyrd's "Free Bird," and namedrops all-American artifacts like Memphis, the White House, rock and roll, and the old movie star of yore, Steve McQueen. The song's music video even features a car chase that hearkens back to McQueen's famed San Franciscan stunt car work in 1968's "Bullitt." And, Crow wears star-spangled pants in the music video and references her own OG hit in the line, "I still wanna have some fun." How is this not all empty fan service and cynical songwriting drafted in sole pursuit of the almighty dollar? Easy: It's self-aware.

There's always been an element of self-awareness to some of the best rock of the 20th century, especially of the arena/theatrical rock variety. Bands like Kiss knew they were ridiculous and reveled in it, just like their fans. This is part of the unspoken agreement that music fans enter into when listening to a band, similar to how movie-goers know a movie isn't real but take it as such for the duration of a film. 

Through knowing glances toward the camera in the music video and lines that would border on self-parody if they weren't intentionally over-the-top ("I ain't takin' s*** off no one / Baby, that was yesterday / I'm an all-American rebel / Making my big getaway"), Crow makes it clear she's in on the gag, but also doesn't mock it. She's locked into our rock tradition, not afraid to make it known, and welcomes people to the party.

Coming last in our song chronology, and possibly the most musically refined of our choices, is "Tell Me When It's Over" from 2019's collaboration-flush "Threads." The song highlights every remaining reason why Sheryl Crow deserves a place amongst rock's greats. Written at a time in her life very different from her younger years, "Tell Me When It's Over" is a post-breast cancer, middle-of-motherhood song from an older, wiser Crow who nonetheless retains the hunger of her younger self.

Musically, "Tell Me When It's Over" demonstrates precisely how the smartest songwriters surround themselves with the best musicians. One listen to a live version of the track from CMT Crossroads on YouTube and you ought to be able to see that Crow's band is a crack team of seasoned pros who effortlessly lock together. Of course, Chris Stapleton and his gloriously powerful voice are on hand for both this live version and the studio track as a duet with Crow. He infuses extra pathos into a song that's already full of soul and flowing with the blues, no matter how country-leaning. Crow's descending pre-chorus vocal line is angelic, especially when followed up with the funky, plucked bassline of the chorus that's reminiscent of nothing less than the Rolling Stones' "Miss You." It's a fine piece of work that demonstrates the experience of years yet isn't made dull by age.

Building on themes established long ago in "My Favorite Mistake," "Tell Me When It's Over" deals with a potential breakup in a way that folks can understand: "But anything's better than hanging 'round together / Knowing that the other one's through." Honest, direct, exposed, and tough all at once: This is Crow at her finest.