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The Best Sheryl Crow Songs

By Deborah Crooks

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Over 11 studio albums and countless singles and collaborations, Sheryl Crow has steadily created an iconic songbook built on a bedrock of clear-eyed truth-telling and rock-solid musicality.

Here are 15 of the best Sheryl Crow songs, according to Holler.

15
Sheryl Crow - Threads Album Cover

Big Machine | 2019

Live Wire

A swampy, blues rocker from her 2019 album, this romp with fellow musical heavyweights Bonnie Raitt and Mavis Staples is as much a victory lap as a great reason for Crow to jam with two of her biggest inspirations.

Showcasing the spirit of collaboration that’s been a throughline of her career, its vibe is pure electricity.

Sheryl Crow - Threads Album Cover

Big Machine | 2019 ? videoThumbnail.image_asset.caption : ''}

14
Sheryl Crow - The Globe Sessions Album Cover

A&M | 1998

Riverwide

This introspective, folk-leaning track from Crow’s third record is a channel change from her usual roots rock.

Using a line from a Walt Whitman poem as a launching point (”I spent a year in the mouth of a whale”) she contemplates how difficult experiences and relationships transform us and make us who we are.

Sheryl Crow - The Globe Sessions Album Cover

A&M | 1998 ? videoThumbnail.image_asset.caption : ''}

13
Sheryl Crow - C'mon C'mon Album Cover

A&M | 2002

Steve McQueen

Crow pays tribute to and takes cues from the famously cool actor for whom the song is named.

Singing “I ain't takin' shit off no one / baby, that was yesterday / I'm an all-American rebel / Making my big getaway", with no shortage of attitude, it earned her another Grammy and turned into a dance hit.

Sheryl Crow - C'mon C'mon Album Cover

A&M | 2002 ? videoThumbnail.image_asset.caption : ''}

12
Sheryl Crow - Tuesday Night Music Club Album Cover

A&M | 1993

I Shall Believe

One of Crow’s earliest compositions is one of her most timeless.

Soulful and melodic, ‘I Shall Believe’ cuts to the heart of faith, pure and simple. “Please say honestly, you won't give up on me / and I shall believe” she sings on the country-gospel hymn.

Sheryl Crow - Tuesday Night Music Club Album Cover

A&M | 1993 ? videoThumbnail.image_asset.caption : ''}

11
Sheryl Crow - The First Cut Is the Deepest Single Cover

A&M | 2003

The First Cut is the Deepest

Amid writing many great songs herself, Crow has amassed a neat collection of covers, including this classic Cat Stevens song about love’s battle scars from 1967.

Her 2003 version gave her another huge radio hit and her first solo country top-40. Nearly 20 years later, it remains one of her setlist perennials.

Sheryl Crow - The First Cut Is the Deepest Single Cover

A&M | 2003 ? videoThumbnail.image_asset.caption : ''}

10
Sheryl Crow - The Globe Sessions Album Cover

A&M | 1998

My Favourite Mistake

‘My Favorite Mistake” perfectly captures the roller coaster emotions that come with being hooked on a cheating lover.

The pain of heartache is sometimes worth its high price, a sentiment she conveys with a knowing wince, a wink and no regret.

Sheryl Crow - The Globe Sessions Album Cover

A&M | 1998 ? videoThumbnail.image_asset.caption : ''}

9
Sheryl Crow - C'mon C'mon Album Cover

A&M | 2002

Soak Up The Sun

A perfect, breezy summer tune, ‘Soak Up the Sun’ reminds listeners to seize the day and have a good time amid life's challenges.

It epitomizes Crow and her frequent co-writer Jeff Trott’s knack for hitting musical sweet spots between pathos and superficiality.

Sheryl Crow - C'mon C'mon Album Cover

A&M | 2002 ? videoThumbnail.image_asset.caption : ''}

8
Sheryl Crow - Sheryl Crow Album Cover

UMG | 1996

A Change Would Do You Good

Populated by quirky characters who are interesting but not the company she actually needs, Crow lays down a funky groove in this infectious smash from her eponymous album.

As usual, she brings the listener along as she figures things out; “Scully and angel on the kitchen floor / and I'm calling Buddy on the Ouija board".

Sheryl Crow - Sheryl Crow Album Cover

UMG | 1996 ? videoThumbnail.image_asset.caption : ''}

7
Sheryl Crow - Sheryl Crow Album Cover

UMG | 1996

Everyday Is A Winding Road

While Crow was inspired by the mental health struggles of a tourmate to write this song on her sophomore album, its message resonates with anyone contending with recovery.

Over an upbeat track, Crow sings a lyric that is at once sympathetic and encouraging; “Lay back, enjoy the show / everybody gets high, everybody gets low".

Sheryl Crow - Sheryl Crow Album Cover

UMG | 1996 ? videoThumbnail.image_asset.caption : ''}

6
Kid Rock - Cocky Album Cover

Atlantic | 2001

Picture

Sung from the perspective of two former lovers pining for each other, despite having moved on to other relationships, Crow co-wrote and performed ‘Picture’ with Kid Rock for his album Cocky.

Crow’s deft vocals carry just the right touch of twang and depth of emotion to make it feel authentic and launch it to the top of the charts.

Kid Rock - Cocky Album Cover

Atlantic | 2001 ? videoThumbnail.image_asset.caption : ''}

5
Sheryl Crow - Tuesday Night Music Club Album Cover

A&M | 1993

Leaving Las Vegas

One of Crow’s songwriting talents is relatability, epitomized by her raw, emotive performance on this rich track from Tuesday Night Music Club.

“I’m standing in the middle of the desert / waiting for my ship to come in” she shouts over a bed of percussive handclaps and acoustic guitar, conveying both frustration and determination.

Sheryl Crow - Tuesday Night Music Club Album Cover

A&M | 1993 ? videoThumbnail.image_asset.caption : ''}

4
Sheryl Crow - Sheryl Crow Album Cover

UMG | 1996

Redemption Day

Crow’s visit to war-torn Bosnia, at the same time as the Rwandan genocide was raging, led her to question global political maneuvering and moral prices paid in the name of strategy.

Johnny Cash famously covered the song just months before he died. She later combined his recorded vocals with her own for a haunting duet on 2019’s Threads.

Sheryl Crow - Sheryl Crow Album Cover

UMG | 1996 ? videoThumbnail.image_asset.caption : ''}

3
Sheryl Crow - Tuesday Night Music Club Album Cover

A&M | 1993

Strong Enough

A deceptively straightforward ballad that packs a revelatory punch, Crow flips the script by being the one to ask a lover “are you strong enough to be my man?”

First included on her debut album, she went on to perform and release versions with both The Chicks and Stevie Nicks.

Sheryl Crow - Tuesday Night Music Club Album Cover

A&M | 1993 ? videoThumbnail.image_asset.caption : ''}

2
Sheryl Crow - Tuesday Night Music Club Album Cover

A&M | 1993

All I Wanna Do

Based on the poem 'Fun' by Wyn Coope, ‘All I Wanna Do’ was, and is, just that: fun.

A breezy, catchy, singable confection of a song about beer-buzz loving, day-drinking buddies whiling away a day in L.A., it encapsulated her character-rich songwriting, winning Crow her first Grammy Award.



Sheryl Crow - Tuesday Night Music Club Album Cover

A&M | 1993 ? videoThumbnail.image_asset.caption : ''}

1
Sheryl Crow - Sheryl Crow Album Cover

UMG | 1996

If It Makes You Happy

Crow had already achieved global stardom by the time she wrote ‘If It Makes You Happy,’ a swaggering slice of country rock from her self-produced sophomore effort Sheryl Crow.

The work signaled to the world that not only could Crow stand on her own musically, but that she was here to stay.



Sheryl Crow - Sheryl Crow Album Cover

UMG | 1996 ? videoThumbnail.image_asset.caption : ''}

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