Sheryl Crow Songs: The Singer-Songwriter's 10 Greatest Hits, Ranked
For 30 years, Sheryl Crow has been one of the most beloved singer-songwriters around, blending a down to earth, bohemian vibe with country storytelling and popstar catchiness. Her songs manage to be simultaneously easygoing and philosophical — they're fun to sing along with, and sound just right blasting out of your car's speakers on a sunny day, yet the lyrics always pack a serious punch.
Crow has racked up some impressive achievements over the years, winning nine Grammys and being inducted into the Rock and Roll Hall of Fame in 2023. At 62, she's also dealt with her share of hardship as she's battled cancer, but thankfully she's bounced back with grace. In recent years, she's won over a new generation of fans (she even recently shared the stage with Gen Z pop starlet Olivia Rodrigo!) and she's just released her 12th album, Evolution.
In honor of her new album (which features the fun single "Alarm Clock"), we're ranking the 10 best Sheryl Crow songs that we had on repeat in the '90s and '00s — and still love today!
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Read on for more of our favorite '90s pop culture!
10. "Tomorrow Never Dies" (1997)
In 1997, Crow sang the theme song for the James Bond movie Tomorrow Never Dies. It initially seemed a strange pairing, as many of Crow's signature songs are more understated than the bombastic anthems often associated with Bond, but "Tomorrow Never Dies" proved a surprisingly potent showcase for her powerhouse vocals.
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9. "The First Cut Is the Deepest" (2003)
Many Sheryl Crow songs have a laidback '60s/'70s feel, and this cover of a classic Cat Stevens song was a perfect fit. While the song has been covered many times over the years, Crow's folky yet poppy interpretation is one of the best, and it earned her a Gold Record.
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8. "Soak Up the Sun" (2002)
"Soak Up the Sun" is the most uplifting of Sheryl Crow songs — and one of her biggest hits. With a boppy tune and upbeat yet slyly subversive lyrics, the song is sure to put a smile on any listener's face, and the lyric "It's not having what you want/It's wanting what you've got" offers an important reminder to appreciate the little things in life.
The song was released in 2002, not long after the traumatic events of 9/11, and its positive spirit had a profound resonance with people hoping to find optimism.
7. "Steve McQueen" (2002)
There are few actors cooler than Steve McQueen, who starred in classic '60s and '70s movies like The Great Escape, Bullitt and The Getaway. Decades later, Crow played tribute to the late star in this rockin' song. The music video shows her wearing leather and driving fast in a car and motorcycle, putting a tough girl spin on McQueen's macho legacy.
6. "A Change Would Do You Good" (1997)
"A Change Would Do You Good" seems straightforward at first (couldn't we all use some change in our lives?) but listen a little more closely and you'll realize the lyrics are pretty quirky.
Crow wrote the song with her frequent collaborator Jeff Trott, who said, "There was a bunch of little non-sequiturs because Sheryl said, 'We need to write some really colorful verses and just get out there and be really abstract.'" They also were inspired by the sounds of '60s soul, and the star-studded music video (featuring Ellen DeGeneres, Jeff Garlin, Molly Shannon and more), is similarly retro, with Crow taking on a role not unlike Samantha from Bewitched.
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5. "Strong Enough" (1994)
"Strong Enough," in which Crow pointedly asks an admirer "Are you strong enough to be my man?," is a poignant, stripped down song with a dash of country flair. The relatable lyrics can apply in all kinds of circumstances, as Crow said that while the song was inspired by "holding my own amongst a bunch of guys" it ultimately felt "thematically universal."
4. "My Favorite Mistake" (1998)
"My Favorite Mistake" features lyrics about a no-good lover, and there's been much speculation as to which man may have inspired it, but Crow will never tell. In a People interview, she said, "It’s still so personal to me that I don’t know that anybody knows who it’s really about. I guess it’s my 'You’re So Vain' moment."
Crow has also called the song one of her favorites she's written, telling Vulture, "It’s the quintessential kind of perfect pop song, out of all the pop songs I’ve written, at least. I still really enjoy it. Other songs I’ve written don’t do that for me." A perfect pop song that keeps people guessing... what could be better?
3. "All I Wanna Do" (1994)
"All I Wanna Do" was Crow's breakout hit, peaking at number 2 on the Billboard Hot 100. Three decades later it remains her highest-charting song to date, and it's easy to see why, given its irresistible catchiness and lighthearted message.
Crow admitted to having mixed feelings about her biggest hit, saying, "I had a love-hate relationship with 'All I Wanna Do' early on because it wasn’t one of my favorite songs. I look at that song now, and I play it with total gratitude because it took me all over the world." Ultimately, the success of the song put Crow on the map and allowed her to take greater risks on her next albums, and it remains one of her most adored creations.
2. "Everyday Is a Winding Road" (1996)
"Everyday Is a Winding Road" is one of Crow's deepest songs. Her lyrics took inspiration from the struggles of her friend Paul Hester, of the band Crowded House, and the title was a direct quote from something he once said about his struggles with depression.
Sadly, Hester died by suicide in 2005, leading to song to take on a new resonance. Reflecting on her dearly missed friend, Crow said, "He inspired the song because... he was such a character and so full of life, and it’s basically about the search for the meaning of life.”
1. "If It Makes You Happy" (1996)
Of all the Sheryl Crow songs, "If It Makes You Happy" is the most anthemic. The chorus, "If it makes you happy/It can't be that bad/If it makes you happy/Then why the hell are you so sad?" has an emotional power anyone can relate to.
The song was the first single from Crow's second album, and expressed her feelings of celebrating her success while also being fed up with the sexism she faced in the music industry. Crow has also said the message of the song boils down to "Quit complaining everybody. Look at the joy in your life" — a message many of us need to hear, especially when it's delivered in such a great song.
