23 of Sheryl Crow's Best Songs: A Definitive Playlist

Sheryl Crow, a name synonymous with soulful vocals and unforgettable melodies, has left an indelible mark on the music industry. For years, fans have debated the ultimate "best songs by Sheryl Crow," a conversation as lively as her own electrifying stage presence. This isn't just a list for casual listeners; it's a journey through the evolution of a powerhouse vocalist and songwriter, exploring the tracks that have defined her career and resonated deeply with millions. Whether you're a longtime devotee seeking a nostalgic trip down memory lane or a curious newcomer eager to discover her musical genius, this curated selection of Sheryl Crow's best work will offer something for everyone. From her bluesy rock anthems to her poignant ballads, we'll delve into the songs that cemented her place as a true icon, highlighting the lyrical depth and undeniable charisma that make her music so enduringly popular. Prepare to rediscover your favorites and uncover hidden gems within this definitive ranking of the best songs by Sheryl Crow.

23 of Sheryl Crow's Best Songs: A Definitive Playlist
SongArtistListens
1. If It Makes You Happy Sheryl Crow 74M+
2. Soak Up The Sun Sheryl Crow 42M+
3. The First Cut Is the Deepest Sheryl Crow 29M+
4. My Favorite Mistake Sheryl Crow 28M+
5. Everyday Is a Winding Road Sheryl Crow 14M+
6. Tell Me When It's Over Sheryl Crow
Chris Stapleton
9M+
7. All I Wanna Do Sheryl Crow 8M+

1. If It Makes You Happy

Upbeat Melody: "If It Makes You Happy" boasts a relentlessly catchy melody that's both instantly memorable and undeniably joyful, perfectly showcasing Crow's songwriting talent.

Anthemic Chorus: The powerful chorus is incredibly singable and uplifting, making it a perfect addition to any feel-good playlist.

Nostalgic Vibe: This track perfectly encapsulates the breezy, optimistic sound of 90s pop-rock, offering a dose of nostalgia for fans of that era.

If It Makes You Happy - Sheryl Crow

2. Soak Up The Sun - 2025

Upbeat Melody: "Soak Up the Sun" features a relentlessly cheerful melody that's instantly catchy and guaranteed to lift your spirits, making it a quintessential Sheryl Crow feel-good anthem.

Nostalgic Vibe: The song evokes a carefree summer attitude, tapping into a specific time and feeling that resonates with many listeners and solidifies its place among Crow's most beloved tracks.

Vocal Delivery: Sheryl Crow's bright, powerful vocals perfectly complement the song's optimistic tone, delivering the lyrics with an infectious energy that adds to the overall appeal.

Soak Up The Sun - Sheryl Crow

3. The First Cut Is the Deepest (Sheryl Crow - 2025)

Sheryl Crow's Vocal Performance: Sheryl Crow delivers a powerhouse vocal performance in "The First Cut Is the Deepest" showcasing her incredible range and emotional depth. Her raw, vulnerable delivery perfectly captures the song's heartbreak.

Timeless Melody: The song's melody is instantly memorable and undeniably catchy, contributing to its enduring popularity among fans and critics alike. It's a beautifully crafted tune that stays with you long after the song ends.

Emotional Resonance: "The First Cut Is the Deepest" resonates deeply with listeners due to its relatable theme of heartbreak and loss. This universal experience contributes to its status as a beloved classic.

The First Cut Is the Deepest - Sheryl Crow

4. My Favorite Mistake (Sheryl Crow - 1998)

Catchy Melody: "My Favorite Mistake" boasts an instantly memorable melody that gets stuck in your head in the best way, showcasing Sheryl Crow's knack for crafting earworm hooks.

Emotional Resonance: The song explores the bittersweet complexities of a flawed relationship with honesty and vulnerability, making it relatable and deeply affecting.

Vocal Performance: Crow's vocals are raw and emotive, perfectly conveying the emotional turmoil and ultimately, the acceptance, within the lyrics.

My Favorite Mistake - Sheryl Crow

5. Everyday Is a Winding Road (Sheryl Crow - 1996)

Sound: "Everyday Is a Winding Road" boasts Sheryl Crow's signature blend of folk-rock and bluesy grit, creating a sound both relaxed and powerful.

Vocals: Crow's vocals are effortlessly soulful, conveying a sense of both vulnerability and resilience that perfectly matches the song's reflective lyrics.

Emotional Impact: The song's reflective lyrics and mellow yet driving rhythm create a deeply resonant and ultimately uplifting listening experience, making it a perfect choice for moments of introspection.

Everyday Is a Winding Road - Sheryl Crow

6. Tell Me When It's Over (2019)

Vocals: Sheryl Crow's and Chris Stapleton's distinct vocal styles blend beautifully, creating a captivating and emotionally resonant duet.

Emotional Impact: The song's melancholic yet hopeful tone explores themes of loss and acceptance, making it a relatable and powerful listen for anyone navigating difficult emotions.

Musicality: The instrumentation subtly underscores the vocal performance, letting the raw emotion of the lyrics and vocals take center stage; a hallmark of Crow's best work.

Tell Me When It's Over - Sheryl Crow,Chris Stapleton

7. All I Wanna Do (Sheryl Crow)

Catchy Melody: "All I Wanna Do" boasts an instantly memorable melody that's both upbeat and slightly melancholic, perfectly capturing the complexities of wanting something you can't quite have.

Sheryl Crow's signature vocals: Crow's distinctive, raspy vocals shine, delivering a performance that's both powerful and vulnerable, making the song's emotional core resonate deeply.

Enduring appeal: Its blend of rock and blues influences gives the song a timeless quality that continues to captivate listeners years after its release, solidifying its place among Crow's best.

All I Wanna Do - Sheryl Crow

8. Steve McQueen (Sheryl Crow - 2025)

Driving Beat: "Steve McQueen" boasts a propulsive rhythm that's both catchy and undeniably cool, perfectly capturing the song's rebellious spirit.

Sheryl Crow's Vocals: Crow's powerful yet vulnerable vocals are a highlight, conveying a complex mix of longing and defiance.

Nostalgic Vibe: The song's blend of rock and blues creates a timeless quality, making it a enduring favorite among fans of Sheryl Crow's best work.

Steve McQueen - Sheryl Crow

9. Tomorrow Never Dies

Catchy Melody: "Tomorrow Never Dies" boasts an instantly memorable melody that gets stuck in your head in the best way, showcasing Crow's knack for crafting earworm hooks.

Powerful Vocals: Sheryl Crow's distinctive vocals are at their peak here, delivering a performance full of raw emotion and controlled power.

Enduring Appeal: The song's blend of rock and pop sensibilities has ensured its place as a timeless classic within Crow's discography, a testament to its enduring quality.

Tomorrow Never Dies - Sheryl Crow

10. Run Baby Run

Upbeat Tempo and Driving Rhythm: "Run Baby Run" boasts a relentlessly catchy rhythm that keeps the energy high, making it perfect for adding some pep to your step.

Sheryl Crow's Powerful Vocals: Crow's distinctive voice shines on this track, delivering a powerful and emotive performance that underscores the song's themes of perseverance and hope.

Anthemic Quality: The song's overall feel makes it incredibly singable and memorable, cementing its place as a true Sheryl Crow classic.

Run Baby Run - Sheryl Crow
  • Good Is Good
    11

    Good Is Good

    Sheryl Crow

    2005

  • Home
    12

    Home

    Sheryl Crow

    1996

  • Anything But Down
    13

    Anything But Down

    Sheryl Crow

    1998

  • Love Is Free
    14

    Love Is Free

    Sheryl Crow

    2008

  • Sweet Child O' Mine
    15

    Sweet Child O' Mine

    Sheryl Crow

    1999

  • A Change Would Do You Good
    16

    A Change Would Do You Good

    Sheryl Crow

    1996

  • Strong Enough
    17

    Strong Enough

    Sheryl Crow

    1993

  • Gasoline
    18

    Gasoline

    Sheryl Crow

    2008

  • Out Of Our Heads
    19

    Out Of Our Heads

    Sheryl Crow

    2008

  • There Goes The Neighborhood
    20

    There Goes The Neighborhood

    Sheryl Crow

    1998

  • Beware Of Darkness
    21

    Beware Of Darkness

    Sting,Sheryl Crow,Eric Clapton,Brandi Carlile

    2019

  • Hard To Make A Stand
    22

    Hard To Make A Stand

    Sheryl Crow

    1996

  • Long Way Back
    23

    Long Way Back

    Sheryl Crow

    2008