Sheryl Crow's 10 Best Songs: Critic's Picks

Mark Seliger
Sheryl Crow

For close to a quarter-century, the music of Sheryl Crow has served as the soundtrack to American lives. Sometimes, that has included some of the most unforgettable up-tempo songs of that time period -- that make you just want to roll down the window, and 'have some fun.' At other times, Crow’s compositions have inspired us to aspire to dream big and make 'A Change' for good.

Whether you prefer her ballad or rocker side, we feel there are plenty of Sheryl Crow songs on this list that will make you nod in agreement, and maybe a few that you had forgotten about. Either way, they stand as a representative of an artist who remains as timeless and as relevant as the moment she first walked into America’s spotlight at the Tuesday Night Music Club!

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10. Sheryl Crow - "If It Makes You Happy" 

This Grammy-winning performance from her 1996 self-titled disc was definitely one of the moodiest performances Sheryl Crow's song catalog. There was definitely a shift in attitude between Tuesday Night Music Club and her follow-up disc, with this being the gritty focal point of that change in sound.

9. Sheryl Crow - "The First Cut Is The Deepest" 

Released as a single from her 2003 The Very Best of Sheryl Crow compilation, her cover of the Cat Stevens classic earned her a huge Pop / AC hit, but also found herself in the Top-40 of the Country charts for the first time as a solo artist.

8. Sheryl Crow - "Strong Enough"

Crow chose to follow up the exuberance of "All I Wanna Do" with a song that stood in stark contrast to the hit that launched her career. This was a highly charged performance where fans got a peek at the artistic flair of the singer -- and fans and fellow artists took notice. A few years later, Travis Tritt recorded an answer to the song, aptly titled "Strong Enough To Be Your Man."

7. Sheryl Crow - "Soak Up The Sun" 

For her fourth studio album, 2002's C’mon C’mon, the singer decided to dial things in a bit with the lead single, a three-minute ode to enjoying the good times, complete with a video shot in Hawaii that made this song a staple of playlists during the summer of that year.

6. Sheryl Crow - "My Favorite Mistake"

Written by the singer and frequent collaborator Jeff Trott, this Sheryl Crow song had people guessing during its’ chart run in 1998. Speculation focused strongly that the lyrics -- about a cheating boyfriend -- could have been about Eric Clapton. Crow never confessed who the song’s subject, but that she was the only one who knew for sure!

5. Sheryl Crow - "A Change Would Do You Good"

 Crow’s 1997 single release found her in a deep state of transition, as she realized that she was in need of something a little more real out of life. In 2008, Crow performed the song at an inauguration event for President Barack Obama.

4. Sheryl Crow - "Steve McQueen"

This fiery 2002 release garnered the singer her fourth Grammy for Best Female Rock Performance, and what a showcase it was for the singer. As she approached forty, the singer reminded us all that age was simply a number -- releasing a song and a video that showed her swagger had only gotten more defined over the course of time. The video was especially effective, with the singer getting to recreate scenes from several of the actor’s film scenes over the years.

3. Sheryl Crow - "All I Wanna Do"

A blockbuster of a debut hit upon its' release in 1994, it might be fair to say that this song was both a blessing and a curse. The release was such a huge success that some fans and critics were probably expecting more of the same for the singer. And, there was a whole other side to her that would be reflected in the Sheryl Crow song catalog. Still, having a worldwide hit that resulted in a pair of Grammy wins is not a bad problem to have.

2. Sheryl Crow - "Everyday Is A Winding Road"

Crow’s music made fans out of many of her fellow Rock artists, and this song was no exception. The original 1996 recording featured harmonies from Crowded House’s Neil Finn, and a few years after her release, no less than Prince covered the song on his Rave Un2 the Joy Fantastic disc.

HONORABLE. Sheryl Crow - "Waterproof Mascara"

On paper, Crow’s 2013 disc Feels Like Home might appear to be somewhat of a failure. In all honesty, that distinction is because Country Radio didn’t give the stunning album a fair shot, as the format was heavily focused on "Bro Country" anthems at the time. While the Kennett, Missouri native has said that playing the radio game was something that wasn’t for her, this album is definitely worth a look. One of the key moments from the album was this breathtaking composition, co-written with Brad Paisley and Chris DuBois.

1. Sheryl Crow - "Can’t Cry Anymore"

It might not be the biggest Sheryl Crow song of all, but this 1995 single from Tuesday Night Music Club about a woman in search of a brand new start without some of the hindrances that had kept her down remains one of her most charismatic performances. The cut was a minor hit in the States, but ironically, the song earned her a chart-topper in Spain, helping to establish her as a fan favorite all around the world.