The Rock and Roll Hall of Fame inductee joined ET to open up the vault and look back on some of her biggest career moments.
It's clear to see that Sheryl Crow has come a long way since her days working as an elementary school music teacher in Fenton, Missouri.
The 62-year-old songstress sat down with ET for a rETrospective, where she looked back at some of the most iconic moments from her long-standing career, from releasing her debut studio album, Tuesday Night Music Club, in 1993 to dropping her eleventh full-length studio album, Evolution, in March.
Although Crow's career began well before she dropped her first album in the '90s, the mom of two reached her first bit of mainstream success when her single, "All I Wanna Do," began to see traction a year after the album's release.
Reflecting on the song's surprise success, Crow tells ET that she initially saw "All I Wanna Do" as a song suited for a "B side" rather than a release single.
"I felt like it shouldn't go on the record and my brother, who was in college at the time, said, 'Our favorite song is 'All I Wanna Do,'' and he's like, 'You've got to put that on the record,'" Crow recalls of her reluctance to record the song. "And then it wound up being the biggest hit!"
"All I Wanna Do" became Tuesday Night Music Club's breakout hit, peaking at No. 2 on the Billboard Hot 100 for six consecutive weeks. It is still Crow's biggest US hit, and earned the singer GRAMMYs for Record of the Year and Best Female Pop Vocal Performance in 1995. The single was also nominated for Song of the Year.
Crow recalls hearing the song for the first time after releasing it while driving back from the dentist. "I was driving through Beverly Hills, coming back from the dentist, when I heard it on the radio and, literally, when you hear yourself on the radio you just want to roll down your window and yell at people going, 'That's me, that's me, that's me,'" she quips.
"The song just sounded good, you know, and it captured something that was authentic to LA in the '90s, then and there, in that moment," she adds. "But yeah, I didn't really think the song was that great and then, who knew?"
When Crow isn't collecting GRAMMYs for her beloved music -- of which she has 9 wins out of 19 nominations total -- she's making appearances on everyone's favorite TV shows alongside her famous friends.
One such appearance was her stint as an advisor for Team Blake Shelton on season 4 of The Voice in 2013.
Crow reveals that she had been asked to be a coach on the NBC singing competition series when the show was being developed before its premiere in 2011. But the Nashville resident wasn't interested in moving to Los Angeles, where the show is filmed.
"Originally, I felt like I didn't want to lock, stock and barrel move back to L.A. I had two small boys [and] I wanted them to have what was, to me, a relatively normal life," she shares. "I can't see picking up again; I mean, they're teenagers [now], I don't want to miss any time away from them, and they're not going to move."
Still, Crow couldn't praise her good friend enough about bringing her onto the show. "I love Blake [and] having him want me to come on -- I mean, he could have anybody so that's a huge compliment!"
It's no surprise that Crow prioritizes her sons' needs over any potential opportunities, the singer has been very vocal about her struggles living in the spotlight and wanting to keep peace in her family's life.
Crow adopted her sons, Wyatt, 16, and Levi, 13, in 2007 and 2010, respectively.
Back in 2022, ET spoke with Crow ahead of the release of her documentary, Sheryl, during which the songstress looked back on not only her struggles with mental health but with being in the spotlight.
"It's an interesting thing for me. Making this documentary felt like I was revisiting somebody else's life," Crow said of the Showtime documentary. "It's so odd now when I think about it, because this morning I got up, I took my kids to school. I have a sick horse, so we had to schedule our horse being put down tomorrow. This is my life now, and I love my life."
She continued, "When I think about before moving here and adopting my children -- I had parties for the Rolling Stones at my house. John Travolta would be there, Gwyneth. That was my life, and my life revolved around being in that world, and I loved it. There was a lot of pressure that went along with being an artist, entering my forties and everybody on the radio being in their teens, this was during the Britney, Christina Aguilera, and there I am turning 40. Then suddenly you're not relevant anymore."
While Crow's daily life has changed, she's far from completely divorced from fame, which she's starting to share with her sons. The two were by their mother's side when she was inducted into the Rock and Roll Hall of Fame in November 2023.
"I think they think their mom is cool if she just keeps a low profile and doesn't embarrass them," Crow quips to ET when asked about how the boys see her fame. "You know, they are teenagers, but I think they're proud of me. They came to the Rock and Roll Hall of Fame, and I think that was really the first time that they got to see like a retrospective of who I was before they came along."
She adds, "I know they're proud of the work, and they love me, but, you know, when we're home, we're like [any other] family. I'm in the school pickup line, and I'm at the ball games, and you know, I'm doing the homework with the kids, and that's the way I love it. So it's an interesting juxtaposition."
And Crow isn't planning on stepping away from the music game anytime soon. Despite telling ET in 2019 that she predicted Threads would be her final album, Crow released Evolution in March.
When asked what inspired the release after her previous comments, Crow says that the album came about as she found herself trying to "figure out what are we doing in our evolution."
She continues: "What are we doing as a society when we're inviting AI to become the thing that informs us? I mean, we're not even understanding what truth is anymore. And to be raising two kids and to watch the vitriol that is being wielded between us -- it's a very strange time."
Crow shares that as an artist, "the only thing that I know to do" is make music from her thoughts. "So that's how all these songs came about," she explains.
From working as an elementary school music teacher in Fenton, Missouri to becoming a nine-time GRAMMY winner and Rock and Rock Hall of Fame inductee, Crow confesses that looking back at her career thus far "makes me a little melancholy."
"But it also reminds me of some really amazing things that I would not necessarily reflect on," she adds. "There's years and years of experience in there and learning how to hold onto my authenticity as a person first and foremost, not as a famous person, not as an artist but, as you know, a living human being with a soul and spirit. It's interesting to watch it playing out. I hope that I'm closer to who I came in as than I am who I became."
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