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If it makes her happy: Sheryl Crow at 60, still going her own way

by Mark McDermott

Wendell and Bernice Crow were among the more musical folks in the small town of Kennett, Missouri.

Neither was a professional musician but both were more than musical hobbyists. Wendell was a lawyer by trade who played trumpet, and Bernice was the town’s beloved piano teacher. They played jazz in a big band that practiced Wednesday nights and played every weekend. The Crow home included three pianos and a rotating cast of most of the town’s musicians.

Even so, Wendell and Bernice were shocked one day in 1963 when they were driving through downtown Kennett and Sheryl, the youngest of their three daughters at 3 years of age, started singing in the backseat. It wasn’t just that she was singing, but how she was doing it – Sheryl sang all the words to the Petula Clark song “Downtown,” exactly like the radio hit, down to every last inflection, even the British accent.

“We were just stunned,” Bernice later remembered, years after Sheryl had become a worldwide rock star and merited her own VH1 “Behind the Music” special. “Because we didn’t know she could do this. And that she wanted to do it.”

Sheryl Crow turns 60 today, and she’s still doing it. Crow possesses that rarest of musical gifts, the ability to write and sing songs that are not just buoyant but meaningful. And she’s a hitmaker: Crow has sold more than 80 million records, earned 9 Grammy Awards, and played all the world’s greatest stages, from the Royal Albert Hall to Carnegie Hall to the Woodstock revival festival and, in May, BeachLife Festival.

And yet, there’s a strange thing about Crow’s stature within the annals of rock ‘n roll. Even though Crow’s forbearers such as Stevie Nicks, Keith Richards, and Bob Dylan consider her a peer, and a new generation that includes Kasey Musgraves, Phoebe Bridgers, and Lorde cover her songs and venerate her as a vital influence – Sheryl Crow is underrated.

If a male musician had produced a body of work like Crow’s and carried three decades of cultural sway, he’d already be in the Rock & Roll Hall of Fame.

Crow knows this, but like everything she does, carries it lightly while keeping it real.

“There are far more male ‘legends’ or ‘rock heroes’ than there are women. I’m not exactly sure why,” she told Nylon magazine. “Motherhood tends to get in the way of longevity….There is something different about men being able to go on the road then come home to something intact. Women don’t have the luxury of that. I don’t know many male husbands who would stay at home while their rockstar wife is out traveling around.”

Another strange thing about Crow’s journey through the world as a musician is that, despite the everlasting buoyancy of her music, nothing ever came easy.

After an idyllic childhood in which she was a baton-twirling majorette, an all-state track star (a hurdler, naturally) and crowned Paperdoll Queen in a beauty contest her senior year of high school, she studied classical piano and voice at the University of Missouri and started singing in a rock band on weekends. She fell in love with a fellow musician in the band, moved to St. Louis with him, became an elementary school teacher, and got engaged. Then she got dumped three months before the wedding because she wasn’t singing Christian songs (the first of three times in her life that an engagement was broken off). She did what she always did, which was to keep on singing. A jingle that she wrote and sang was picked up by McDonald’s and earned the equivalent of two years' salary as a school teacher. And so the small-town girl took that money and drove to Los Angeles, where she didn’t know anyone. She was 25 years old.

Crow heard that Michael Jackson was looking for backup singers for a big global tour, crashed the auditions, and got the job. She became Jackson’s favorite backup singer on the tour, and the tabloids made up stories that he’d offered her $2 million to have his baby. The reality was even uglier – Jackson’s manager, Frank DiLeo, sexually harassed her the entire 18-month tour, vowing to make her a star, but then vowing to blackball her from the music industry when she would not comply with his advances. When Crow arrived back in LA, she made a demo and took it to all the record companies, and was rejected by everyone. This was the age of Madonna and Paula Abdul, and Crow’s own music was relegated to “blue-eyed soul,” which had no place on the radio at the time.

“Even though I've been singing R&B and pop every night in front of 75,000 people and was in all the tabloids and all the magazines, I came home, went to every record company and played my music, and had everybody say, ‘We don't know what to do with that,’” Crow recalled in a radio interview with Canadian Public Radio. “I went home to total silence, and I went back to waitressing. I felt like I had missed the bus, and it was my fault. “

She fell into a crushing depression. Her mom drove out from Missouri and literally got her daughter out of bed.

“You don't want that,” Crow said in an online interview with Rolling Stone’s Brian Hiatt a few years ago. “You just don't want your mom to show up when your whole life has been about making sure everybody thinks that you're perfect and great. It's just…we're all made differently, and if we're really honest with ourselves and really allow ourselves to experience all the facets of life and all the emotions that go along with it – it's hard sometimes.”

Crow picked herself up and began singing again. She got a gig as a backup singer for Don Henley, made a demo that A&M records liked, and so finally landed her own record deal. But after more than a year in the studio working with Sting’s producer, Hugh Padgham, the resulting album was big and shiny and loud…and not at all what anyone wanted, including Crow. She and the record company agreed to not release it. Her recording career started with complete failure, and second chances are rare in the music industry.

Crow was undeterred. She caught wind of a group of L.A. musicians that included songwriters Bill Bottrell and David Baerwald that had casual gatherings every Tuesday night beginning at a Mexican restaurant and ending up jamming at someone’s house. She was invited to join.

The rest is musical history. Sheryl Crow’s first record, The Tuesday Night Music Club, sold 8 million copies and won three Grammy Awards, and included the eternal mega-hit, “All I Wanna Do.” It was listed by NPR among the top 100 rock albums of all time.

But even Crow’s breakthrough came with almost unspeakable pain. One of her co-writers, Baerwold, was friends with author John O’Brien, who’d written a novel called “Leaving Las Vegas” (eventually a movie starring Nicholas Cage). Baerwald brought the title to the Tuesday Night Music Club and they wrote a beautiful song of the same name, but none but Baerwald knew O’Brien had written the title. The author, who was a troubled soul and a chronic alcoholic, killed himself right as the album was charting in 1994. Though O’Brien’s family absolved her of any responsibility, his death deeply affected Crow.

“There's always a wall that we all slam into, and our innocence or our naivete is shattered,” Henley told VH!. “She's never been quite as light-hearted ever since then.”

Then came what is always the most difficult challenge, the follow-up to a first record that is a blockbuster. Bottrell, who had produced Tuesday Night, traveled to New Orleans with Crow to work on the next record but quit on the very first night of recording. Crow did something unheard of at the time, especially for a woman in the music industry – she produced her own record.

“It forced me to man up, or woman up,” she told Hiatt. And to really dig deep and find who I wanted to be artistically.”

And because she was a woman, Crow faced skepticism that she’d even written her first, collaboratively created record (Bottrell, despite their differences, years later confirmed that Crow had been the lead writer on every song). Crow found it liberating.

“There was a huge spectrum of emotions that went along with that record,” Crow told Rolling Stone. “One of being burned, and of being highly misunderstood and very underestimated. But the euphoria of feeling like, ‘Well, nobody believes I can do anything anyway, so I'm going to do what I want to do.’”

She pointedly titled her second album Sheryl Crow. Released in 1996, it won the Grammy for Best Rock Album (and two other Grammys), went triple platinum, and scored five hits, including a song that would inspire a generation of female musicians, “If It Makes You Happy.” The album was an announcement of a sort: Sheryl Crow was here to stay.

First of two parts. See part two next week. Sheryl Crow plays BeachLife May 15


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