Sheryl Crow has carved a unique place in the landscape of American music. Emerging in the early 1990s, she blended rock grit with pop sensibilities, country twang, and bluesy undertones to create a sound that was both familiar and refreshingly new. Across a career spanning decades, Crow has gifted us with a rich catalog of songs that are introspective, anthemic, and always undeniably catchy. From her breakthrough hits to her deeper album cuts, Sheryl Crow’s songs resonate with authenticity and a keen observation of life’s complexities. This list delves into 20 essential Sheryl Crow Songs, showcasing the breadth and depth of her remarkable artistry.
20. Prove You Wrong (2019)
From what was initially billed as her final album, Threads, “Prove You Wrong” is a collaborative powerhouse. Sheryl Crow joins forces with Stevie Nicks and Maren Morris in this rollicking, barroom-ready track. The song crackles with a playful energy as the trio of vocalists seems to revel in putting down a former flame who underestimated them. It’s a testament to Crow’s ability to bring together diverse talents and create something genuinely fun and spirited, even late in her career. The song’s infectious rhythm and empowering message of self-assuredness make it a standout from her later work.
19. Soak Up the Sun (2002)
“Soak Up the Sun,” the lead single from C’mon, C’mon, offers a burst of pure, unadulterated optimism. After the introspective depths of her self-titled album and The Globe Sessions, this track is intentionally bright and breezy. While some might find its sweetness a touch saccharine, the infectious chorus is undeniably effective. Crow paints a picture of simple pleasures, finding joy even in a “crummy job” that “don’t pay near enough.” Released in a post-9/11 world, “Soak Up the Sun” was deliberately designed to lift spirits, and its enduring appeal suggests it succeeded. Its recent cover by Gen Z indie artist Soccer Mommy further underscores the song’s timeless quality and cross-generational resonance.
18. There Goes the Neighbourhood (1998)
Recorded in New York’s Meatpacking District during its late 90s transformation, “There Goes the Neighbourhood” captures the area’s bohemian spirit. This track from The Globe Sessions is a surreal and strutting character study, populated by the “Hells Angels, transvestites and very colourful people” that Crow observed. The lyrics are a stream-of-consciousness mix of cultural references, from Peter Ustinov to heroin chic, culminating in a nod to Calamity Jane. The song’s quirky charm and vivid imagery offer a glimpse into a specific time and place, filtered through Crow’s unique artistic lens.
17. Cross Creek Road (2019)
Sheryl Crow excels at crafting rock ballads that possess a raw, vulnerable edge, and “Cross Creek Road” from Threads is a prime example. Featuring Lukas Nelson on backing vocals and a verse from Neil Young, the song begins as a delicate piano ballad, imbued with poetic melancholy (“I took the blue sky and turned it into rain”). It gradually evolves into a swaying country singalong with its chorus before dissolving into a coda of fractured guitar feedback. This masterful blend of tenderness and grit, characteristic of Crow’s signature sound, makes “Cross Creek Road” a standout track.
16. Riverwide (1998)
A quieter, more contemplative moment on The Globe Sessions, “Riverwide” opens with a striking literary allusion (“I spent a year in the mouth of a whale / With a flame and a book of signs”). The lyrics then drift into cryptic territories, touching on themes of broken relationships and mortality. According to Crow, the song arrived fully formed, and its latter half, enriched by lush strings, adds a spiritual dimension. “Riverwide” demonstrates Crow’s capacity to create songs that are both lyrically intriguing and musically evocative, showcasing her depth as a songwriter.
15. What I Can Do For You (1993)
Before achieving mainstream success with Tuesday Night Music Club, Sheryl Crow was a backing vocalist for Michael Jackson’s Bad tour. This period, however, was marred by alleged sexual harassment from Jackson’s manager, Frank DiLeo, an experience that profoundly impacted Crow. “What I Can Do For You,” a lesser-known single from her debut album, directly addresses this experience. Sung from the perspective of a predatory figure, the song is a chilling portrayal of power imbalance and manipulation, making it a significant, albeit uncomfortable, piece within Crow’s discography.
14. Ordinary Morning (1996)
Sheryl Crow, her self-titled sophomore album, explores the complexities of newfound fame and success. “Ordinary Morning,” the album’s closing track, encapsulates this theme of disillusionment. It portrays a sense of suffocating paranoia, suggesting that achieving your dreams isn’t always the idyllic experience imagined. The song blends jazzy piano with raw, crunching guitars, creating a tense and unsettling atmosphere. Crow’s whispered final lines, “Don’t you wanna slip away?” perfectly capture the desire for escape from the pressures of fame.
13. Strong Enough (1993)
Tuesday Night Music Club‘s massive commercial success in the US was such that even its fifth single, the folk-tinged ballad “Strong Enough,” reached the Top 5. This song revealed a different facet of Crow’s artistry, highlighting her vocal vulnerability. Her “careworn vocal” delivery perfectly complements the lyrics, which delve into the search for stability and strength within a turbulent relationship. “Strong Enough” is a testament to Crow’s versatility and her ability to connect with listeners through raw emotional honesty.
12. Weather Channel (2002)
In the 2022 documentary Sheryl, Crow openly discusses her struggles with depression. These struggles came to a head during the making of C’mon, C’mon, a period where she felt overwhelmed and feared being forgotten if she took a break. “Weather Channel,” the album’s heartbreaking closer featuring Emmylou Harris, directly confronts these anxieties. Crow’s cracked vocal delivery is deeply affecting as she sings lyrics like, “Can you make it better for me / Can you make me see the light of day.” The song is a poignant and deeply personal exploration of vulnerability and the search for solace.
11. Redemption Day (1996)
Inspired by Crow’s visit to Bosnia to support American troops, “Redemption Day” is a powerful Dylan-esque protest song. It critiques the international community’s slow response to global crises. Set against a steady, martial beat and ominous guitar twangs, Crow directly challenges politicians (“Come leaders, come ye men of great / Let us hear you pontificate”) and questions the motivations behind delayed interventions (“Was there no oil to excavate?”). Despite its specific origins, “Redemption Day”‘s potent anger and message of accountability remain timeless, further emphasized by Johnny Cash’s 2003 cover.
10. Anything But Down (1998)
Sheryl Crow’s lyrical style can sometimes be emotionally ambiguous. However, “Anything But Down,” a vibrant single from The Globe Sessions, takes a more direct approach. The verses list everyday coping mechanisms – lighting cigarettes, running baths, pouring wine – before the chorus bluntly reveals the one-sided nature of a relationship. The song features a standout bridge culminating in the sharp kiss-off line: “It was so much easier before you became you.” This track showcases Crow’s ability to blend catchy melodies with lyrics that are both relatable and incisive.
9. Now That You’re Gone (2008)
Following her battle with breast cancer and the end of her engagement to Lance Armstrong, Crow returned to her musical strengths with Detours, the album succeeding the commercially disappointing Wildflower. “Now That You’re Gone” perfectly balances Crow’s pop sensibilities – the melodic lift into the chorus is expertly crafted – with lyrics celebrating newfound independence. Rolling Stone aptly compared it to Kelly Clarkson’s “Since U Been Gone,” but “20 years wiser,” highlighting Crow’s mature perspective and enduring pop craftsmanship.
8. A Change Would Do You Good (1996)
Sheryl Crow faced considerable pressure with her self-titled second album. Despite the massive success of her debut, questions lingered about the extent of her own songwriting contribution, fueled by public comments from her (male) collaborators. “A Change Would Do You Good” directly addresses this, playfully mocking producer Bill Bottrell in the first verse. The song is melodically buoyant and fuzz-laden, with a caustic second verse partly inspired by Madonna. It’s a defiant and catchy response to critics and doubters, asserting Crow’s artistic autonomy.
7. Run Baby Run (1993)
Released as her debut single to initial indifference, “Run Baby Run” has since become a staple in Crow’s repertoire. Written in her storytelling mode, it portrays a character caught between contrasting worlds: the nostalgic conservatism of the past and the idealistic protest of the hippy movement. The protagonist’s primary lesson learned is to run and avoid looking back, a pattern that extends to her relationships. “Run Baby Run” is an early example of Crow’s narrative songwriting and her exploration of complex themes within accessible pop structures.
6. Hard to Make a Stand (1996)
Crow’s pop inclinations can sometimes obscure her politically engaged songwriting. However, tracks like “Hard to Make a Stand” from her self-titled album serve as powerful reminders of her social commentary. The album itself faced controversy for criticizing Walmart’s gun policy on “Love Is a Good Thing” (leading to the retailer refusing to stock it). “Hard to Make a Stand,” a classic-sounding, Rolling Stones-esque rocker, tackles the grim reality of anti-abortion violence. It describes a friend who “Went to take care of her own body / And she got shot down in the road.” The song is a potent example of protest music that is both morally driven and viscerally impactful, never resorting to preachiness.
5. All I Wanna Do (1993)
Built upon the then-obscure 1987 poem “Fun” by Wyn Cooper, “All I Wanna Do” marked Sheryl Crow’s long-awaited commercial breakthrough. This gloriously carefree anthem seamlessly blends rock, country (evident in the slide guitar wah-wahs), and adult-pop, proving irresistible to 90s US radio. Reaching No. 2 on the charts, it solidified Crow’s status as a major rock star. Remarkably, its ubiquity hasn’t diminished its infectious energy and enduring appeal, remaining a quintessential 90s feel-good track.
4. If It Makes You Happy (1996)
Bruised by the fallout from her debut album’s success and exhausted from constant touring, Crow adopted a grittier approach for her self-produced follow-up. “If It Makes You Happy,” the lead single, showcases this shift. Having developed a more characterful, raspy vocal style and backed by a swaggering rock sound, Crow directs the chorus’s central question – “If it makes you happy then why the hell are you so sad?” – inward, while also delivering a warning to those who perceived her as simply “nice and homely”: “I’m not the kind of girl you’d take home.” The song is a raw and assertive declaration of independence and self-awareness.
3. Home (1996)
“Home,” a delicate ballad from Sheryl Crow, features Crow’s versatile voice reduced to a near whisper. It intimately examines a relationship that has transitioned from passionate to platonic. Written during the dissolution of her second engagement, the song explores the comfort of familiarity versus the allure of the unknown, the latter symbolized by the bridge and Crow’s yearning to see the sunrise “in a stranger’s arms.” “Home” is a beautifully melancholic exploration of love, loss, and the bittersweet nature of relationships evolving.
2. Everyday is a Winding Road (1996)
Crow quickly discovered that fame can be destabilizing, and her second album largely grapples with regaining balance. “Everyday is a Winding Road,” inspired by former Crowded House drummer Paul Hester, celebrates embracing risks and living in the moment. The song’s soundtrack is a heady mix of slide guitar, fuzzed Moog bass, and driving percussion. It also garnered notable fans, including Prince, who famously covered it in 1999. The song’s message of resilience and its infectious musicality have contributed to its enduring popularity.
1. My Favourite Mistake (1998)
Crow reportedly considered shelving The Globe Sessions entirely, feeling exposed by the raw honesty of her lyrics, which shifted from veiled narratives to intensely personal confessions. The reaction to the lead single, “My Favourite Mistake,” with its allusions to a cheating ex, fueled intense media speculation (Eric Clapton and Jakob Dylan were prominently mentioned). However, the personal turmoil is overshadowed by the sheer brilliance of “My Favourite Mistake,” arguably Crow’s greatest achievement. Its defiant rock riffs and dramatic organ tremolos are beautifully undercut by the resignation in Crow’s vocals as she grapples with conflicting emotions. The song masterfully balances a glimmer of hope for change with a deep-seated sense of inevitability, capturing the complex push and pull of human relationships. “My Favourite Mistake” is a powerful and enduring testament to Sheryl Crow’s songwriting prowess and her ability to transform personal experience into universally resonant music.
