My 10 Favorite Sheryl Crow Songs, Ranked
by Marisa Torrieri Bloom
After decades in the music business, rockmommy Sheryl Crow continues to put out rootsy Americana songs that turn into timeless classics. Here’s a list of our 10 favorite tunes by the boy mom (of sons Wyatt Steven Crow and Levi James Crow) and LIlith Fair siren.
#10: “LEAVING LAS VEGAS” (TUESDAY NIGHT MUSIC CLUB)
This 1993 hit about the ups and downs of being a performer is one of the most relatable songs in Crow’s catalogue, and still ranks as one of her best singles to date.
#9: “ROLLER SKATE” (BE MYSELF)
With its funky, disco beat and synth-pop hooks, this 6-year-old summery tune showcases Crow’s vocals in a whole new way. I love the post-chorus call to action, “put your phone away, let’s roller skate!”
#8: IF IT MAKES YOU HAPPY (SHERYL CROW)
From the first strum of the muscular guitar to the singalong refrain, this tune from Crow’s self-titled album is a storyteller’s dream. The way she belts out the chorus is just unreal.
#7: EVERY DAY IS A WINDING ROAD (SHERYL CROW)
I dig everything about this song, from the percussion to the video featuring Crow at a playground. Why am I a stranger in my own life? Why am I so wound up? This song ponders these and other big life questions, while inviting the listener to escape and enjoy.
[SEE RELATED: MY TOP 10 FAVORITE GRACE POTTER SONGS IN HONOR OF THE ROCKMOMMY’S 6/20 BIRTHDAY]
#6: IN THE END (IN THE END)
Is it too late to turn back now? Too late to see the light? These are the serious questions a seething Crowe considers amid the acrimonious political climate of the 2020s (which has, sadly, persisted, long past Covid’s heyday). But what I love about this song is that showcases Crow’s ability to shapeshift and draw inspiration from anger and turn it into art.
#5: ALL I WANNA DO (TUESDAY NIGHT MUSIC CLUB)
Word has it this catchy, carefree tune from Crow’s 1993 breakout record is based on the once little-known poet Wyn Cooper’s 1987 work, Fun. It’s a little country, and a little rock n’ roll, with cool, electric-guitar and jazz riffs and weird sounds that come together in the most serendipitous way.
#4: SOAK UP THE SUN (C’MON C’MON)
This upbeat tune from Crow’s 2002 album is sweet and relatable, with a synth-pop drum beat and the sunniest, slide-guitar chorus – it’s also (apparently) a Gen X mom favorite (ahem!).
#3: MY FAVORITE MISTAKE (THE GLOBE SESSIONS)
Some say the song’ is a masterpiece because of its searing rock riffs buoyed by subtle organ tremolos – but it’s the emotional heft that drives it: The song about a relationship with a man who proves to be unfaithful and is widely believed to have been written about her relationship with Eric Clapton.
#2: THE FIRST CUT IS THE DEEPEST (C’MON AMERICA)
This Cat Stevens 1967 classic is a pure joy to cover, with its simple chord progressions and catchy choruses.
#1: STRONG ENOUGH (TUESDAY NIGHT MUSIC CLUB)
Crow’s three-decade-old “Strong Enough” – stands the test of time – kids know it, Gen Xers love it, and rising stars cover it (as they should).
Marisa Torrieri Bloom is the founder and editor of Rockmommy.
