At many different points in Sheryl Crow’s life, becoming a pop music icon seemed highly unlikely. Like when she was a school teacher in Missouri. Or even when she was a backup singer on Michael Jackson’s Bad Tour, performing anonymously in the shadows behind the world’s biggest star.
But when Crow burst out in 1993 with her debut, Tuesday Night Music Club, she immediately established herself as one of the most reliable singer-songwriters in the business, a title she can still claim two decades later.
Take a look at our picks for the 10 best Sheryl Crow songs and see how they compare with your own choices.
“Easy” perfectly matches its title. The lead single from Crow's 2013 country album Feels Like Home was a warm tune that glided over a nice melody and contained appealing lyrics about forgetting vacation and enjoying life at home instead.
9. “The First Cut is the Deepest”
The most recent chart-topper of Sheryl’s career – it hit #1 on the adult contemporary chart in 2004 – “The First Cut is the Deepest” was a Cat Stevens song from 1967 that Crow turned into her own tale about overcoming brutal heartbreak.
8. “If It Makes You Happy”
The first track from Crow’s second album, the Grammy-winning “If It Makes You Happy” presented a new side of Sheryl – one with a bit of snarl and attitude, as well as vocal abilities that went well beyond anything she had shown on her first record.
7. “Leaving Las Vegas”
Crow’s first hit remains one of her best. “Leaving Las Vegas” featured some of her most memorable lyrical snapshots, from the gaudy neon streets to the crossroads trucker demonstrating his might, which left her ultimately searching for a way to “take this losing hand and make it win.”
6. “Redemption Day”
“Redemption Day” was a dark, bluesy album track from 1996’s Sheryl Crow that documented what she saw as society’s ignorance of important social problems. Johnny Cash later recorded the song for his final album American VI, an honor that Crow called her biggest accomplishment as a songwriter.
5. “My Favorite Mistake”
The 1998 hit “My Favorite Mistake” was a bit more subtle than some of Crow’s more infectious earlier singles, but it’s one of those songs that became more appealing with each repeated listen. The singer has called it one of her favorites from her career.
4. “Soak Up the Sun”
“It’s not having what you want / It’s wanting what you’ve got,” Sheryl advised on this undeniable smash from 2002’s C’mon C’mon. Wise advice from a performer who had been through numerous ups and downs and lived to sing about them.
3. “Everyday is a Winding Road”
On her self-titled second album, Sheryl did most of the writing and production herself, and that includes “Everyday is a Winding Road,” a pop song that found room for heavy percussion and killer slide guitars that took the track to another level.
2. “All I Wanna Do”
The endearing narrative tale about sitting at a bar and observing her surroundings earned Crow three Grammy Awards, cementing her place in pop music history before her first album cycle was even finished.
1. “Strong Enough”
The Sheryl Crow track most likely to be remembered 100 years from now is the heartfelt ballad “Strong Enough,” which deftly described a tortured relationship. “God I feel like hell tonight,” she began, before later urging, “Lie to me / I promise I’ll believe.” The #5 hit from 1994 tops the list of the best Sheryl Crow songs.