“How many people here are in their 30s?” Sheryl Crow demands of the audience, guitar slung across her back in the middle of a set at Toronto’s Budweiser stage. The response, while audible, is unimpressive.

She then asks about those in their 40s, to a slightly more substantial cheer. When Crow wonders aloud how many people are in their 50s, though, the roar is almost deafening. She grins, strumming the opening chords of “Still the Good Old Days,” a collaboration with Joe Walsh from her 11th studio album, Threads (out Aug. 30), about living it up in middle age. “But we’re still having fun, right?”

“Fun” has been a defining word in the 57-year-old multiplatinum, Grammy Award-winning singer-songwriter’s career (as has its frequent rhyme, “sun”), for better or worse. Crow’s beachy, upbeat songs have always had a healthy sense of levity. But “fun” has also become a backhanded compliment of sorts when it comes to discussions of her music — a suggestion that her catalog and her songwriting are enjoyable but mostly trivial. Crow’s hits endure though, and nearly three decades into her career, she’s still fighting for the respect she deserves instead of being just another “woman in rock.”

She is, plainly, having plenty of fun though. Her clear, bright voice sounds as good, maybe even better, than it ever has. (“I actually have more range than I used to,” she’ll tell me later, almost offhandedly.) Onstage she struts around in black skinny jeans with silver fringe running down each leg to match sparkling silver sneakers, occasionally wagging her knees in and out like Elvis Presley. Even as she runs through a more or less complete roster of nothing but hits — kicking off with “A Change Will Do You Good” and “All I Wanna Do” — her smiles seem sincere and her enthusiasm infectious.

It wasn’t always this way. “Fifteen years ago, I was burned out and didn’t want to play those songs,” says Crow the day after the show, sipping English breakfast tea in the Four Seasons Toronto restaurant. “I still played the hits, but I didn’t enjoy it and I didn’t want to see the audience. But something changed — obviously breast cancer [which she was diagnosed with and successfully had treated in 2006] made a big difference. Now I want to see what a song meant to people. That means more to me than anything else. Especially in the day and age when people have their phones up at your shows, those songs where their arms are in the air and they’re just singing really loud — you can’t be sick of that. You’re not allowed to be sick of that.”

What Crow has grown sick of, or at least wants to stop doing, is making albums. Though she just signed with Big Machine Label Group in February, she says Threads, which includes collaborations with everyone from Stevie Nicks to Brandi Carlile, will be her last. “I have loved the tradition and the challenge of making records, but it doesn’t feel like the end of anything. It felt sad for a while when people stopped wanting to pay for music, but I’ve just made my peace with all of it.”

So Crow is not retiring — just keeping up with the times in her own way, by sticking to touring and releasing singles. The clarity she found after adopting her sons, Wyatt, 12, and Levi, 9 — who also serve as part of her team of guitar techs, for $5 a show — helped her forget about the skeptics and the critics and the sexists, and instead appreciate the new generation of young artists she has inspired, as well as her own tight-knit network of iconic musician-friends, many of whom are featured on Threads.

“I’ve never been the best guitar player or the best singer,” says Crow. “But I’ve always gotten ideas across, better than probably anyone else could have. They all came from me.”

You have seen the industry move from the LP era to what it is today. What do you think are the upsides to technology?

The ability to go in, make your own record and not be dependent on somebody offering you a budget — and, in return, owning your masters. As young artists become more savvy, hopefully they can sell records that they already have in hand. Then they can go into business with a label without losing their art in perpetuity.

Your masters were some of those lost in the Universal Music Group fire, right?

It’s really difficult for me to even wrap my mind around it. It is such a predicament: You can’t sue a record company for allowing something to burn that you gave up your right to own. But having said that, I’ve found out that not all my masters burned. [UMG confirmed that masters for all of Crow’s A&M-released albums survived the fire.] For me, it’s indicative of the business: Wherever commerce and art are joined together, art takes the back seat.

When you started making this album, you weren’t attached to a label. Why did you sign with Big Machine?

I made the record in my barn and it cost a lot of money, but I didn’t want somebody to say, “Look, we’ll pay you, but we get to keep the masters.” I loved everything that Scott [Borchetta] had to say. It is my last album, and he felt above all that the songs needed to be heard — not just the songs that could make everybody richer, but the songs that mean something. He was like, “I believe in this; I’m going to work it.” And they have worked, as my 9-year-old says, their man-berries off.

How did you connect with Scott?

I was shopping the country record [2013’s Feels Like Home]. He listened to it and was like, “I can’t do anything with that. It’s hard enough to get women [on country radio], and people want to hear you make a Sheryl Crow record” — and he was right. At first, I was like, “What?! I’ve been very influenced by country music.” But I really appreciated that he wasn’t going to jerk my chain.

That’s so interesting to hear, considering that two of the most exciting young women in country — Maren Morris and Kacey Musgraves [who recorded her Grammy-winning Golden Hour in Crow’s in-barn studio] — have cited you as an influence.

I want to be a source for young artists, male or female, for creativity and advice. I would love for more people to make records in my barn. I was just telling [British singer-songwriter] Lucie Silvas the other day, “I want you to come and just experiment.” When the light gets shone on you commercially, there’s a lot of pressure to follow that up. With somebody like Kacey, it was important for her to do some self-discovery artistically and not have the record label involved. When I was first hearing it in the barn, I told her I could feel that she was shutting out the world and finding herself. It was so beautiful and brave.

When did that moment of self-discovery happen for you?

The second record [Sheryl Crow] was probably my Kacey moment. I felt like everything that people thought about me — and there were a lot of stories out there about my first record — wasn’t telling the full story. It was like, “I’m in the studio by myself and have nobody who really believes in me, so that’s actually to my benefit.” Working with Trina [Shoemaker], a female engineer, made a monumental difference. Being able to explain in my novice way to her the sounds I wanted — and her just embracing my ignorance — was fantastic.

It’s also interesting to see how many younger artists have covered some of those songs. When did you first notice that?

A few years ago, Lorde and HAIM did “Strong Enough.” I was just like, “Oh, my gosh, that’s amazing.” Not just anybody, but two of the hippest artists out there? It was really flattering.

“If It Makes You Happy” is basically canon at this point.

I mean, that was in a Britney Spears movie [Crossroads]. You know when it’s in a Britney Spears movie, you have passed go. (Laughs.)

Do you feel like you’re considered one of rock’s canonical artists? Do you want to be?

I have a pretty low image of myself, mainly because when I first came out I was totally shunned by my peers — the Seattle scene, Courtney Love and Beck and R.E.M. and Billy Corgan — because what I was doing was much more rootsy. You either liked me or you didn’t, and it wasn’t cool to like me. The people who wrote me off way back then have never liked me. As a result, they don’t know that I have anything other than pop hits.

I had some people tell me that I was eligible for the Rock & Roll Hall of Fame [in 2018]. It never occurs to me that I would even be considered a rock artist. Most people think I’m lightweight. Eighty percent of my catalog is not the pop stuff — but the big hits are.

You and Bonnie Raitt, who is on Threads, have had somewhat similar careers in terms of being women who play instruments and lead bands and make rootsy, approachable rock music.

I told her this: “I saw you when I was 17, and I saw you playing guitar like a man.” And that’s not to sound derogatory, but I had never seen a woman do that. Right then I picked up a guitar and started teaching myself how to play. I can’t touch it like she does, though.

The tough part is getting people to understand that not all women artists should be grouped together.

It doesn’t make your music female rock. I mean, I was watching Chrissie Hynde, who has been around forever, and like, people, that is rock. That’s rock’n’roll. She may be a female, but you need to forget that.

For women, it’s obviously harder to be taken seriously — in every field, but particularly in music. You and Raitt both got pushed into this adult-contemporary category when in fact you make rock music.

It’s really funny. I’m not as sensitive about it as I used to be. Early on, the reviews would mention what I wore or what I look like. We were opening for John Mellencamp, and I would think, “Why don’t they mention what John’s wearing? Or what he looks like?” (Laughs.)

It’s true: In most of the early coverage of your career, male and female writers alike talked quite a bit about, frankly, finding you sexy. How did you deal with that at the time?

My first record, the label turned away my photo shoot. They were like, “You’re prettier than that.” And I said, “But this is what I look like — I don’t want to be sexy just so that people will check out my music.” I put on an oversize jean shirt — I was like Billie Eilish — and I liked that. I wanted to be taken seriously. At least we’re having the conversation these days. People are more aware that there can’t be a double standard.

You have been politically engaged from the beginning: On your first album, there’s a song [“What I Can Do for You”] about sexual harassment, almost 25 years before the #MeToo movement. How was it received?

Frank DiLeo [Michael Jackson’s former manager, whom Crow named as the subject of the song after it came out] filed a lawsuit against me. Then he died of a massive coronary. Not because of me — I’m sure there were other skeletons that might have been more of a burden. I have a history of [talking about politics]. I wrote a song on the second record, “Love Is a Good Thing,” about Walmart selling guns to kids, and I got banned at Walmart, the only store in most of Middle America that sold records. But once you make a first impression, it’s really hard to win people back with album tracks. And that’s fine. I’ll still keep writing about the hard stuff.

You mentioned that your favorite karaoke song is “Picture,” your collaboration with Kid Rock. Is it tough to be associated with him now, given how far you have politically diverged from each other?

All I can say is that it is an incredible journey being a human being. You have to find a way to have compassion, even in the worst of situations. Putting out hate messages and vitriol is just never OK. All the people who say, “Shut up and sing,” on my social media, they’re not going to make me stop or change my mind. My mom has this great saying: “You can’t possibly wish for them to be more miserable than they already are.”

How do you remain physically and mentally strong enough to stay engaged with the music after all this time?

I actually feel more engaged and empowered than I have in years. I think part of that is that there was a really big transition in my life, around 2004-2005, where I had just latched on to some not great influences. But coming out on the other side of having had cancer was liberating, in a weird way. I quit thinking about what people thought. I quit thinking I needed to be productive all the time. I quit putting myself in this box of what life is supposed to look like: fall in love, get married, have babies. I didn’t feel like I was mired down in the muck that I had managed to collect through the years. I dropped a thousand skins.

It’s often underappreciated when successful women are able to choose their own path.

The thing that makes me mad is that it’s almost like I’m bucking the system — like I’m cramming my foot in the door and jamming my way in, when really every woman should be allowed to walk through that door and ask for her due. To be able to direct her own missions. I’m a bit of an outsider because of the system. But I’m just doing what it is I want to do.

What do you want people to take away from this final record and your catalog as a whole?

You know, to be perfectly honest, I don’t care. I made the record kind of selfishly, for the experiences and the love of not only what [my collaborators] have brought to me but for the love of the people themselves. I’m still floating on all that. I don’t even fool myself into thinking that people will hear it as it is — unless they buy the vinyl, and thank God for vinyl. If people like it, that’s great, and if they don’t, I’m sorry, but they’re missing out.

This article originally appeared in the July 27 issue of Billboard.

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