Last November, the Rock and Roll Hall of Fame welcomed its new illustrious class, which included pop icon Kate Bush, Country legend Willie Nelson, and, of course, Sheryl Crow. But while her success has been undeniable, many decried her inclusion, saying that she isn't rock and roll enough to enter the Hall.
Now, this has been an issue for debate for a while within the Hall's inclusion process, but it became especially prevalent for Crow because she has never really been defined by one genre. She's not simply a pop, country, or folk singer because she's been all of them before. She has fun radio singles, conscientious folk ballads, and fast paced rock classics.
In fact, that's one of the reasons that Sheryl Crow has managed to remain such a music icon decades later. She began her career with folkish pop tracks, but eventually crafted full folk, pop, country, and even blues albums. Sure, you can call her a pop singer since she's been steadily popular since her debut album, but that doesn't properly do justice to the multifaceted career she has carved out for herself.
With such a varied career though, Crow has numerous songs that showcase her versatility, lyrical whimsy, and powerful vocals. She sure does have folk, pop, country, and rock hits, yet they all unabashedly retain her signature style.
As such, I've collected what I feel are her ten greatest songs. I took into account many aspects, such as commercial success, impact on her career, and how well the songs have stood the test of time. Some are confessionally devastating, while others are pure slices of pop fun, but all are unmistakably Sheryl Crow.
10. "100 Miles From Memphis"- 100 Miles From Memphis
Starting off with the title track from her R&B and soul inspired album, "100 Miles From Memphis" might just be Crow's most underappreciated song. While it was released a few years after her popularity peaked, it still showcases many of her strengths as a songwriter.
With a bluesy intro, the sound is the perfect backdrop for someone driving alone at night, perhaps searching for something or someone. We quickly find out that the singer is yearning soulfully, as they are headed to someone who's worth driving all night for. Crow adds some distinct sensual notes like "faded blue jeans" and a "tequila soaked dream" so that there's a grounded familiarity to this mysterious affair.
However, the song is all held together by its chorus, a fully blown pleading for her lover to leave with her. As Crow's cool, but husky vocals beg, it becomes clear how committed she is to saving this love. Each rhyming line hits harder than the last until the song title is released as one final whispering effort on Crow's behalf.
It's classic Crow in many ways, building an atmospheric mood before adding a passionate romance to get swept up in. The soul inspiration is also utilized perfectly, as this love starts to feel like a divine rescue from the small town she's trapped in. Building on her folksy reputation, "100 Miles From Memphis" shows how Crow can incorporate new sounds into her old themes without missing a single beat.
incorporates different genres to build on time tested themes.
9. "Leaving Las Vegas"- Tuesday Night Music Club
Another traveling song primed for the desert, "Leaving Las Vegas" exemplifies the fun folk pop that Crow brought early in her career. One of the seminal singles from Tuesday Night Music Club, "Leaving Las Vegas" was one of Crow's first songs to reach mainstream audiences. There's little wonder as to why though, as it remains one of the best showcases of her powerhouse vocals.
Lyrically, the song is straightforward, digging into the details and regret of someone who's lost it all in the excesses of Sin City. However, Crow's raw vocals elevate the song from a one note expression into a full blown exit of empowerment. As she belts the titular chorus, Crow announces proudly that there's nothing more that Vegas can offer, so she must leave.
Yet, the emotional vulnerability that Crow brings makes this about more than gambling. Her ferocious choral cry is a reminder that sometimes we have to leave everything we've known behind to move on with our lives. While Vegas has done nothing for her, it's a city designed to comfort and entice you at every level. It'd be easy to enjoy those neon lights forever, but she must move on to salvage her life.
Even for anyone who has never visited Vegas, Crow's song can leave you with a bittersweet feeling of empowerment. While the drumbeat and clap along are certainly enjoyable, "Leaving Las Vegas" shows how Crow tackles life head on, fully expressing her emotions every step of the way.
8. "My Favorite Mistake"- The Globe Sessions
Of Crow's recurring themes in her music, heartbreak and the dissolution of love some of her most powerful. It's no surprise then that she has some phenomenal breakup songs, one of them being the hit single "My Favorite Mistake."
Rumored to have been inspired by her relationship with Eric Clapton, "My Favorite Mistake" encapsulates the conflicting emotions of a toxic relationship. Throughout the song, the singer emphasizes how her lover is growing distant from her. He comes home late, feigns interest in her, and even has a secret lover.
While it sounds like an awful situation, Crow sings the chorus with an earnest longing that shows that she's not ready to give up on this relationship. Even though she knows things are likely over, she can't let go, rendering the whole experience a mistake she can't stop making.
With an acoustic backdrop and tender vocals that are often vulnerable, the indecisive lyrics lead to one somber track. There's a sad relatability here too, as many people become attached to lovers who just aren't worth the time. Crow never condones the romantic dilemma she's trapped in though. All "My Favorite Mistake "does is acknowledge how painful it can be to love someone, lose them, and then love them after they've gone.
7. "Steve McQueen"- C'mon, C'mon
While Crow does have a tendency to pen thoughtful tracks, she also has a knack for free spirited personal anthems. An outlaw at heart, Crow often reminds her listeners that she's a free soul who must always do what she wants. As such, her hit single from C'mon, C'mon, her poppiest album, does exactly this under the titular allusion of "Steve McQueen."
A famous actor from the 60's who was best known for driving fast and looking cool, Steve McQueen provides the perfect outlet for Crow to channel her freedom. With a revving acoustic guitar, Crow spells out exactly how she lives. She has to say how she feels, she has to drive fast, and she has to have fun doing so. The chorus emphasizes the last part with a bevy of energy led by Crow's bellowing vocals.
While it's not her most complex song, it does attest to one of the most prominent truths in Crow's music: life is to be lived right now and to the fullest. Like Steve McQueen, Crow embraces the fast paced nature of life and rides it the best she can. The freedom of being able to do so is important to her, but only because life is too short to do anything else.
It's a sentiment other Crow tracks have embraced, but it's affectively utilized here with tremendous rock and roll spirit. "Steve McQueen" would not only net Crow another Grammy, but it also provided fans with one of her most captivating songs that can make anyone feel free as a bird in a few mere seconds.
6. "Everyday Is A Winding Road"- Sheryl Crow
Although Crow's songs are often thoughtfully moving or inescapably jovial, sometimes she opts for something that's just relatable. In "Everyday Is A Winding Road," Crow delivers a slice of life song that could appeal to just about any listener. Unsurprisingly, she nailed this universal appeal, as it would go on to be one of the biggest songs of her career.
Released as a single for her second eponymous album, "Everyday" takes a lyrically straightforward approach. Crow doesn't give us some heavy outpour of emotions or complexly layered contradictions. Instead, she notes some seemingly arbitrary details about a "vending machine repair man" and "coffee and nicotine."
While these details seem inconsequential, they're crucial in the character that Crow builds. The singer here is just an average girl, not reaching the intellectual or social heights of the people around her. Despite this, she does the best to live her life, fully actualizing the winding adventures that life brings her.
Once again, Crow is measuring life by her own rules. While there are merits and benefits of chasing the goals society pushes us towards, it's important not to miss out on the moments here right now. Crow even cheekily sings, "Jump in, let's go," inviting the listener to join in on this adventure right now. It isn't Crow's most complex assessment of life, but "Everyday" offers undeniable truths in a song that's just as undeniably catchy.
5. "Real Gone"- Cars (Original Motion Picture Soundtrack)
For most artists, a song recorded for the Cars soundtrack would be an odd footnote for their career or a fun fact to bring up on trivia night. But Crow isn't most artists. Instead of phoning it in for the Pixar production, Crow went all in on "Real Gone," a song as brash and fast paced as Lightning McQueen himself.
Here, Crow takes a note from earlier hit "Steve McQueen" and let's the freewheeling spirit of racing take it up a notch. There's once again a revved up feeling to her opening hook, perfect for the beginning of a race. Shortly after though, Crow begins reeling out distinctly American traits that makeup the racing culture, such as Chevrolet.
But the true lynchpin is her undeniable chorus that lets the song pour out even faster. Crow might belt out, "Slow down, you're gonna crash," but the adrenaline has already set in and the song's in full effect. By the time she reaches that "Real gone" to end the chorus, the guitars have already pushed us into a full racing mode.
It's not a tremendously focused song, but it perfectly encapsulates this unhindered American spirit that lies at the heart of auto racing. Also, it's nearly impossible to listen to and not want to experience the thrills of fast driving yourself. It's catchy, it's full of energy, and proudly boasts of the culture Crow grew up on. One of her most iconic songs, "Real Gone" not only earned Crow an Oscar nomination, but it solidified her as one of the great Americana songwriters of our time.
4. "All I Wanna Do"- Tuesday Night Music Club
Sometimes, an artist is best remembered for their breakthrough hit, whether it's their best song or not. While "All I Wanna Do" isn't quite number one here, it is a tremendous example of how Crow's songs offer slice of life writing that can often feel cinematic.
The song begins with an iconic spoken intro by Crow, letting listeners know that this is the LA music scene exploding right before them. After, Crow begins her detailed tour of a bar she's inhabiting and the people there with her, offering descriptions that are both witty and viscerally gripping. From the man next to her who "wants to have a bit of fun before he dies" to the people washing cars on their lunch break, the mundane world of a bar at noon seems like the most intriguing place in the world.
Yet, despite everything around her, Crow maintains that she's only here to do one thing: have some fun. Like the stranger next to her, the world's concerns don't exist in this LA bar. There's just beer and the good company to share it.
This lively carefree spirit is common in Crow's music, but it's never as layered as it is here. There's the infectiously grooving music that follows the fun chorus, but there's also details that pinpoint the psychological state of the two main characters, who intake the world at a far different rate than us. A pop song with developed lyrics and a jovial attitude, "All I Wanna Do" is still Crow's biggest hit today for obvious reasons.
3. "Soak Up The Sun"- C'mon, C'mon
While Crow has been successful in a multitude of genres, she's never shied away from being a pop singer, especially early in her career. For her fourth album, C'mon, C'mon, she fully embraced the pop sound and released her most radio (and summer) friendly song, "Soak Up The Sun."
Despite being a fully blown pop fest, Crow still takes time to develop the overall theme of "Soak Up The Sun." In the first verse, she remarks how her friends have fun without her, as she's too broke to join them. She adds a touch of irony too, as her communist friend won't let her join because of her lack of money.
However, Crow doesn't despair in the face of fiscal adversity. Instead, she opts to simply enjoy what she has, even if that's only the sunlight at the moment. Once again tapping into the carefree spirit of her independence, Crow fully invests in living in the moment no matter what everyone else does. She presents it as simply as ever here, proudly telling everyone what she's going to do and inviting every listener to join her.
With a fine pop sound and vocals that exude glee, "Soak Up The Sound" maintains the carefree spirit that has become associated with Sheryl Crow. It's not her most complex or emotionally driven song, but it's crucial to the independent songwriter image. Most of all, it's a breath of fresh air that reminds us to have fun while we can, even if we have nothing else.
2. "Strong Enough"- Tuesday Night Music Club
On her debut album, Tuesday Night Music Club, Crow demonstrated many of her great strengths as an artist. You could see her vocal prowess in "Leaving Las Vegas," her whimsy in "The Na Na Song," and her tenacity for having a good time in "All I Wanna Do." However, she's most powerful when she's being completely vulnerable, such as when she let her emotions pour out in the tenderly sung ballad, "Strong Enough."
While "Strong Enough" wasn't her biggest hit off the album, it has resonated with fans due to its raw presentation of emotion. In the song, the singer confesses the overwhelming turmoil she's facing. She feels angry, frustrated, and lonely, yet she still wants her lover to stay. She asks if he's strong enough to be her man, practically begging him to stay despite the lies and emotional whirlwinds it might include.
Musically, there's not much else to this song besides an acoustic guitar. However, that keeps the spotlight on the confession at hand, with Crow's pleading vocals driving the song. The brutally honest lyrics are given an equal straightforwardness by Crow, rendering the entire song realistically vulnerable.
By being so honest, "Strong Enough" showcases a Crow who's not afraid to work through her feelings, despite the implications they might bring. With just a guitar and her voice, Crow encapsulates the addiction and rage relationships can cause us to feel. By capturing the neglect and anger of a wayward romance, "Strong Enough" is not only an enthralling track, but one of Crow's greatest accomplishments.
1. "If It Makes You Happy"- Sheryl Crow
While Crow has released a plethora of hits in a multitude of genres, one song has always been her best since it's release. Despite only peaking at number ten, there's no choice for the greatest Sheryl Crow song besides "If It Makes You Happy."
Starting with an iconic guitar riff, Crow seems to drag her feet into the rest of the melodrama within the song. Soon after, she begins singing about the adventures she has been on as a rock star. However, she presents them in a surreal way, saying she played music for mosquitos and searched through thrift store jungles for items owned by celebrities.
Oddly though, Crow admits that the first verse is made up, showing some discrepancy between her emotions and realty.
She then jumps into the chorus with bellowing vocals, as she practically screams the titular question. In fact, the entire chorus is Crow debating over whether or not the life of global stardom is worth it or not.
Although playing for crowds and shopping in New York would excite anybody, Crow describes them in a way that makes them sound more exhausting than fulfilling. She knows that being a rich and famous pop star is the epitome of success in America, but she can't convince herself that it actually makes her happy, thus rendering her to mope through her fantastic life.
What makes this song Crow's best though is how it captures her signature elements. The vocals are sardonically sung until the chorus allows her to show off her impressive range, which is full of emotion here.
Lyrically, she's at her best, using surreal descriptions and obscure details to craft a life that Crow isn't sure she wants. Most of all, "If It Makes You Happy" allows Crow to confess her true feelings, maintaining the authenticity she always carries.
When all put together, "If It Makes You Happy" becomes an introspective look at success that matches the gloom of the decade that produced it. It's a track that reflects both the conscientious and emotional sides of Crow, while still being a crowd pleaser. As well renowned as any of her songs, "If It Makes You Happy" remains an effectively brilliant song that could only come from the mind of Sheryl Crow.
