How Sheryl Crow Went From Fired Waitress to Michael Jackson’s Backup Singer to Grammy-Winning Superstar

Sheryl Crow returned to the Stern Show on Tuesday to talk to Howard about her new studio album “Be Myself,” as well as perform some of her new music and classic hits. Sheryl’s road to musical success actually started in TV — that’s where her singing voice was heard nationwide for the first time in a McDonald’s commercial.

“I was playing in a band and this guy who was doing session work in town came in and said ‘Will you come in and sing this commercial?'” Sheryl recalled to Howard. At the time, Sheryl was making a living as a school teacher in Missouri, earning about $17,000 a year. She took the commercial gig and recorded various voices for the spot which eventually got played on television coast to coast.

“I made $42,000 which was more than two years of teaching,” Sheryl said.

Determined to see just how far her singing could get her, Sheryl moved to Los Angeles. “First thing I did when I got to L.A. is I took my demo tape to every studio,” she told Howard. In the interim, she got a waitressing job at a café in the San Fernando Valley. Her ambitions got the best of her, however, when she broke the restaurant’s rule prohibiting self-promotion and passed her demo along to a diner who wanted to hire her for a Toyota commercial.

“I got fired for giving my tape out because I wasn’t supposed to do that, but badda bing, badda boom … I got that gig,” she said. “It paid $67,000.” Even after so many years have passed, Sheryl said she remembers what she made on early jobs because those paychecks meant so much at the time.

She wasn’t done breaking the rules just yet, though. While recording backups on a Johnny Mathis record, Sheryl overheard some of the other singers talking about auditioning for Michael Jackson as one of his background singers. Sheryl wanted to tryout, too, but hadn’t been invited.

“So, I just found out where it was and I went,” Sheryl admitted. “I go in, I sign a clipboard, they don’t ask me anything.”

Next, Sheryl was asked to stand in front of a camera and introduce herself to Michael on tape. “I looked in the camera, I said, ‘Hey Michael, my name’s Sheryl Crow. I just moved here six months ago, I’m a singer, I’d love to go on the road with you,’ and that was it. And then they called me back and then they put me with three singers. I hadn’t even sung yet.”

Sheryl isn’t sure if the first round of auditions was to judge the singers’ personalities, but if it was based on looks she told Howard she still looked like a school teacher back then. She got the job and went on tour with the King of Pop, doubling his voice on songs like “Billie Jean” and “Dirty Diana.”

“We did like 30 days of rehearsal and then, wham bam, we’re in front of 65,000 in Tokyo,” Sheryl said. “It was unbelievable when I think about it. I didn’t even own a passport.”

However, Sheryl said she was sometimes manipulated by others while on tour with Michael, being told that her hotel room was bugged and that she was replaceable. “I think that’s the nature of when you have somebody who’s so famous, everybody is paranoid about their job,” Sheryl said.

“The gift in that whole tour was getting to just be on the side, not only doubling him but watching him,” Sheryl told Howard. “There were things about him that were totally otherworldly … things that he created that no one had ever seen. In fact, I was in the audience when he did the moonwalk for the first time at the Grammys.”

Touring with Michael helped Sheryl make a name for herself as a backup singer as well as a songwriter for other famous musicians, like Celine Dion, Phil Collins, and Tina Turner, to name a few. “I needed to make money and, also, that was what I knew how to do,” Sheryl explained. But when it came time for her to break out on her own, she told Howard how Don Henley advised her to stop supporting other artists and start saving her best songs for herself.

“He was actually very instrumental in my getting started,” Sheryl said.

She landed a deal at A&M Records, got into the studio, and made an album, but then she had second thoughts. The sound she had created was “slick” and not at all what she wanted her solo album to be. So, she made the decision not to release it.

“It was hard. It was a bad feeling,” Sheryl said.

After hearing whispers that her label was ready to drop her, Sheryl joined a jam session on Tuesday nights. It was there she found the sound she wanted for her debut album, as well as its title.

“Tuesday Night Music Club” included Sheryl’s first breakout hit “All I Wanna Do,” which was a combination of a Marvin Gaye groove and a Wyn Cooper poem. The single climbed to No. 2 on the charts and earned Sheryl a trio of Grammys, including Best New Artist.

While her newfound fame netted her millions in record sales, Sheryl told Howard it also led to some conflicts. Some of her old jam band buddies began taking credit for the music on Sheryl’s debut album, alleging Sheryl had very little to do with the arrangements. She dismissed those stories Tuesday morning and opened up to Howard about dealing with negative press and losing her producer Bill Bottrell, who decided to not work with Sheryl on her second studio album.

“I felt like the whole world hated me,” Sheryl said.

That’s when she wrote “If It Makes You Happy,” a song Sheryl described as being about “anybody that ever was mean to me.” It made it onto her self-titled sophomore album alongside another track titled “Everyday Is a Winding Road,” which almost got left on the cutting room floor.

“I just didn’t think it was that great of a song,” Sheryl told Howard. “I don’t know anything.”

Sheryl wrote “Everyday Is a Winding Road” about Crowded House drummer Paul Hester who committed suicide shortly after Sheryl and her band started opening for them on tour. The mixer on Sheryl’s second album insisted she include the track due to its subject matter. As a single, it hit No. 11 on the charts and was later covered by Prince.

“I never play that song where I don’t get to the end of it and hear [Prince] in my ear go, ‘Sheryl Crow, y’all,'” Sheryl told Howard on Tuesday, referring to a live performance she did with him in 1999 at Lilith Fair. The two formed a friendship but had a disagreement once over a show Sheryl was doing in New York’s Central Park.

“He just had very, very staunch beliefs about ownership,” Sheryl told Howard. That concert was being put on by American Express and after Sheryl invited Prince to perform at it, he refused.

“He came down on me pretty hard and it just hit me at a moment when I was feeling super fragile,” she continued. However, Sheryl said there was no “rift” between them — they simply lost touch with one another. After Prince’s death, she wished they had kept in contact.

“You have to seize the moment, every opportunity, to tell the people that you care about that you care about them. And I wish I would have done that more,” Sheryl said. She also bought into Howard’s theory that Prince’s personal injuries might have been caused by jumping around in his signature high heels. Stevie Nicks even once told her about playing basketball with Prince while he wore pumps.

Speaking of Stevie Nicks, Howard asked Sheryl about rumors she almost joined the band Fleetwood Mac. Sheryl revealed she was close to coming on as a new member but things simply didn’t line up. “I wish I would’ve. I wish I could have,” she said.

Howard heard it was longtime member Lindsey Buckingham who had a problem with inducting Sheryl into the band. “Well, I felt like if there was gonna be bad blood when I joined, that perhaps maybe I shouldn’t. I didn’t want to upset something that was already so beautiful,” Sheryl said. “I would still love to do it. I’m putting it out there.”

For now, Sheryl’s a solo act with a new album coming out on April 21. After performing her single “Halfway There,” Howard commended Sheryl on still being able to rock.

“I’m funky for a middle-aged white woman,” she joked.

Howard was especially fond of her use of the wah-wah pedal on her new song. “You know what’s wrong with the wah-wah pedal? Nothing!” Sheryl replied.

Watch Sheryl perform “Halfway There” live on the Stern Show (below).