Back to the Hits: Sheryl Crow Revisits The Rises of Her 7 Solo Top 20 Singles on the Hot 100

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Before the touring industry fully reopens, Sheryl Crow has devoted multiple projects this summer to the live presentation of her catalog. On Friday (June 18), “Sheryl Crow: The Songs And The Stories – A Live Solo Performance” will feature the singer-songwriter sharing the stories behind her hits and deep cuts in her first full livestream concert, recorded at the “little church” on Crow’s Nashville property. Less than two months later, Crow will deliver Live From The Ryman & More, a new live album featuring her hits as well as some key live collaborations, set for an Aug. 13 release.

“I wound up going back and just exploring a lot of old songs, over a 30-year career of writing and recording,” Crow tells Billboard of the livestream, which will feature the artist playing solo and sharing extended anecdotes (more details to watch here). “Once I started doing that, I started feeling like, ‘The stories that go along with this stuff are really worth telling,’ and I had never done that before.”

Since making her debut with 1993’s Tuesday Night Music Club, Crow has traveled the world, sold millions of albums and won nine Grammys for her vulnerable, blues- and country- influenced brand of pop-rock. She’s also scored seven solo top 20 hits on the Billboard Hot 100 chart over the course of her career (as well as two collaborative top 20 hits, alongside Kid Rock on 2002’s “Picture” and as part of the Stand Up To Cancer anthem “Just Stand Up!” in 2008).

As part of Billboard’s new Back to the Hits series — and to preview her in-depth livestream concert — Crow revisits her seven solo top 20 hits on the Hot 100 and tells the stories behind their chart success, from her Grammy-winning first smash to the cover that unexpectedly crossed over to pop radio.

“All I Wanna Do”
From: 1993’s Tuesday Night Music Club
Hot 100 Peak: No. 2

Crow: For one thing, that was a song that was really bandied about as whether it was going to go on the record. I really felt like it was a throwaway. [Producer] Bill [Bottrell] was on the fence about it. But my little brother, he came to me and said, “You have to put that on the record. That is the song my friends and I couldn’t stop [playing]. That’s the song, that’s the big hit.” I just thought he was crazy, but we did wind up putting it on. And he was right. I told him after that song got into the top 10 that I wanted to hire him as my new A&R guy, but he wasn’t willing to quit his own job to do that.

But, yeah, it was surreal. And it was also strange, in that it wasn’t really a song that I loved. One of the reasons was that the lyric was taken from a poem, “Fun,” by this guy named Wyn Cooper, who is a professor at a liberal arts college in Vermont. After [initially] using that as the lyric, I said, “Well, I’ll just write another set of lyrics.” I wrote five different sets of lyrics, and none of them felt — they all felt extremely calculated. They didn’t feel like that poem did. And it’s one of those remarkable instances where that lyric just spoke to a moment, and it wasn’t going to be replaced.

Somehow or another, it was the song that resonated with so many young people — this down-and-out, apathetic lyric that celebrated itself with an upbeat chorus. People from South America to Russia to Japan, all these places that that song took us, were singing the lyrics. It was just bonkers.

Billboard: How transformative was that chart rise of the song for your career?

I mean, it completely changed the trajectory of my career. I was nominated for Grammys that year, and I won record of the year and best new artist. This was at a time when the Grammys really made a huge difference in your record sales, and it also created a visibility that no one would have until that moment. That’s what the Grammys TV show did. I mean, it was a real game-changer — it was all due to the fact that that song just exploded.

“Strong Enough”
From: 1993’s Tuesday Night Music Club
Hot 100 Peak: No. 5

I don’t think that I could have had another top 10 song on the album had I not had an explosive song come out first in “All I Wanna Do.” “Strong Enough” wasn’t an obvious single, but it definitely was the same personality singing it. The same person that sang “All I Wanna Do” was representing her vulnerability in “Strong Enough,” and I think people really latched onto it. You know, the vocal on that is very imperfect, but very authentic. At that time, there wasn’t really anything that sounded like that on the radio. It was also great for me, because I really loved the song and it really was a personal song for me.

Seeing it now in a list of back-to-back singles and top 10 hits, it really is amazing how different the two songs are.

And it was amazing to have [“Strong Enough”] come out and do as well as it did, because we’d been already on the road for a year and a half before “All I Wanna Do” took off. And when it took off, we went back out on the road, for about another year. And in the middle of that, we were in Europe when “Strong Enough” hit — and it didn’t just hit in the States, it hit in Europe as well. It just felt so… it’s hard to even explain it. It felt so validating, to have not just the one-off, but to have another song come off the same album. I felt like, “Okay, so now I’m not just a fluke.”

“If It Makes You Happy”
From: 1996’s Sheryl Crow
Hot 100 Peak: No. 10

This album felt completely different, because I produced it, for all intents and purposes, and it actually felt like my debut record, much more than the Tuesday Night Music Club record. And yes, there was an immense amount of pressure to follow up the massive album sales of that first record. But it was also quite a lot of overexposure that started happening in the end, and people just being tired of me, and people speculating about what kind of artist I was.

To be able to have “If It Makes You Happy” come out and do so well, it felt much more like my debut — here I am, this is who I am, and I’m here to stay. And also, the sort of in-your-face lyrical content, for me it was so pointed that it just feltgreat to have that song take off.

It was really a fun song in that, when we went out and played it live, people were just — I mean, they would yell it. But it was a summer anthem, and an all-year-long anthem. Anyone who had any kind of frustrations in their lives, that was where you got it out of your system, that chorus. It became sort of a zeitgeist, and thankfully so.

“Everyday Is a Winding Road”
From: 1996’s Sheryl Crow
Hot 100 Peak: No. 11

You know you’ve grown up when this is the theme song of Home Town Makeover on HGTV and you’re super proud of that! You know what I mean? You know you’re a middle-aged woman when you’re just so excited that your song is on HGTV. (Laughs)

Yeah, that song, like “All I Wanna Do” was on the first record, that time was hanging by the skin of its teeth as far as making the record, because it was written about someone that I had known and my engineer Tchad Blake had known, who had taken his own life. And Tchad had gone through the death of his wife during that record. He said to me, “You have to put this on the record, because ‘I’m a stranger in my own life’ means more to me than any other lyric.”

So I wound up putting it on there, and I’ve always thought of that when that song comes to mind. Everytime I sing that lyric, I think of him, and I think of everybody who’s struggled. But also, it’s a testament to how songs can re-create meaning. Last year, we were going through quarantine and people were losing jobs and losing loved ones. I would play that song and really feel the weight of that particular lyric. When you write a song, you just never know how much meaning it’s going to maintain.

Did it feel bittersweet at all as the song was becoming another hit?

I mean, I guess bittersweet, but more so, it was — and continues to be — life-affirming for me, because the whole idea behind the song is that we’re all just trying to find our way. Joy is this nebulous thing, and feeling “okay” has to be relative to something. If you’ve never experienced joy, then what are you measuring your happiness against? And that’s what the song is about. We are constantly taking detours, getting thrown off, and yet everyday is a new day, and it’s filled with the possibility of getting better and getting closer to our authentic self. So for me, it’s a song that’s super encouraging.

“My Favorite Mistake”
From: 1998’s The Globe Sessions
Hot 100 Peak: No. 20

[Songwriter/producer] Jeff Trott and I wrote that song really quickly in the studio — I was on bass, he was on guitar. I just had a bunch of lyrics that came out, I filled in the gaps, and we finished it within an hour. That never happens! And I was so convinced that I had stolen it, that it had already been written, because it seemed so familiar — so much like an already realized pop song — that I called my publisher and sent it to her. I called Aimee Mann and said, “I want you to listen to this, tell me if I stole this from Squeeze, or, have you written this song?” Nobody knew it, nobody ever heard anything that it sounded like. This was just one of those pop songs that just felt like you had grown up with it.

It’s the only song of mine that when I hear it on the radio, I really enjoy it. Most of the time when I hear my other songs, I tend to turn the radio off, but I enjoy that song. I love playing it. It feels good in my heart. It’s just a good pop song.

“Soak Up the Sun”
From: 2002’s C’mon C’mon
Hot 100 Peak: No. 17

This [becoming a hit] was really unexpected. I’m a terrible judge of what is going to be a big hit and what isn’t, and I would not have thought that song was going to be a big hit. It didn’t seem like anything else on the radio. Everything else was sort of grungy, and this was definitely a straight-up pop-rock song.

But for me, there were so many underlying meanings to the song that I’m sure a lot of people missed. I still felt that I could stand behind that song, as not just a pop song, but a diatribe about — no matter how much we put our energy and our attention on wealth and on brand and imaging ourselves on MTV and VH1, that we are missing the whole point. None of this has meaning unless we can look around us and figure out how to sustain this organism that we live on, this planet. Bentleys and gold faucets and gold toilet seats, none of that stuff is going to bring any kind of satisfaction unless we can sustain life on our planet. That’s what the whole point was.

When the song took off and you started experiencing people singing along with this bright, catchy chorus, was it frustrating to see not enough people pick up on the lyrical nuances?

I’m always grateful when something resonates with people, and my job isn’t to be Debbie Downer and point out every single thing that’s wrong. I want to write songs as a result of how I see things or how I feel about things. And it is in some ways predictable, as far as my musical history — the verses will be filled with meaningful, contemplative observations, and then you have this upbeat, fun chorus. Whenever I write a song, I let go of it, and how people see it or relate to it is out of my hands. And I’m okay with that.

“The First Cut Is The Deepest”
From: 2003’s The Very Best of Sheryl Crow
Hot 100 Peak: No. 14

It was kind of funny, because it was on a greatest hits record. The greatest hits was something that I was not that keen on doing because, you know, in some ways for an artist, it feels like you’re signifying the end of something — like, “Okay, here’s the end of the first half of my career!” Or “Here’s the end of my career!” And so when they suggested we put a couple of new songs on there, I was a little cynical about it.

I was working with [producer/songwriter] John Shanks at the time, and when he suggested “The First Cut is the Deepest,” I was like, “That’s a great idea. It’s a great pop song, people know Rod Stewart’s version, they know Cat Stevens’ version. We can make it our own, and it would be fun for us to go out and play.” And then it wound up doing really well, as if it was a new song. On what was already a record full of well-known songs, it was kind of an added surprise.

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