Crow wrote the song in five minutes in the studio, live on the microphone. It's an odd number for her, in a way, since she's never been married. And yet there is an emotional residue to the song that resonates in her own life. On her way to rock stardom, Crow has made choices, and not all of them have been without personal cost.

"I'm sort of at a point now where I'm looking at my life and wondering why I've never been married," she says. "I'm sort of looking at my life and experiencing some regret, wondering if I'd gone down this road, instead of that road, what my life would have been like."

For the 35-year-old singer-songwriter, the road chosen has stretched from modest beginnings to the top of the pops: a childhood spent in the Missouri town of Kennett; college at Mizzou; teaching in St. Louis; jingle and session work in Los Angeles; back-up singing for Michael Jackson; rock stardom in her own right.

It also is a road that has been littered with controversy, and some long bouts of loneliness.

Today, Sheryl Crow would seem to have it all: two multi-platinum selling albums under her belt, five Grammys on her shelf, sold-out tour dates behind and in front of her. Her videos have been shown on MTV, and she's practically been the house artist on the music channel VH1. She's sung with Pavarotti, been joined on stage by the likes of Emmylou Harris, rocker Joan Osborne and the Band's Levon Helm. There's even been a rumored romance with Eric Clapton.

But beneath the glitzy appendages of fame, the Missouri native has also learned that success these days carries an enormous price tag, especially for women.

Small Town Saturday Night

Sheryl Crow grew up in the Bootheel of Missouri, in Kennett, population 10,941, a town roughly 200 miles south of St. Louis. It is the place, more than any other, where her heart remains.

It is genuinely something of a different world in Kennett, far more Southern in its feel than Midwestern. White tufts dot the roadside, clear signs that the cotton industry butts up to this edge of the state.

When you first pull into town, there are signs that the corporate, homogenizing reach of modern America has extended down into this burg. There's a Wal-Mart superstore, a McDonald's, a Taco Bell, a Pizza Hut and a strip mall with a Dollar Store.

And yet most of Kennett still reveals a compelling throwback quality to another era -- the clock here turns on small-town time. The local paper, The Daily Dunklin Democrat, is all of 14 pages thick. The stores that ring the town square -- Mitchell Drug Store, the Downtown Flea Market, the A.J.K. Shop -- still retain a '50s storefront feel, while further up the road Kennett Bowling Lanes bears a sign declaring "Friday Night All You Can Bowl."

Bernice Crow, Sheryl's mother, is a petite, brunette piano teacher who turned 60 in May. She has known her husband, the attorney and amateur trumpeter Wendell Crow, all her life. They both grew up in nearby Caruthersville, and have called Kennett home since 1959. They raised four children here: Karen, Kathy, Sheryl, Steve.

Sheryl Crow was born Feb. 11, 1962. She grew up in the family's two-story brick house, three minutes from the square by car, a comfortable home with a music room and a back porch where, as Kathy Crow puts it, "we sit outside and fling a burger on the fire once in awhile."

When Sheryl was growing up, Wendell and Bernice Crow played in a local big band. "We usually practiced on Wednesday night, and a lot of it wound up at our house. So the kids heard it always," says Bernice Crow.

By the time Sheryl was 3, she was busy entertaining her family by singing "Downtown" in a near perfect imitation of the Carnaby Street songbird, Petula Clark. Bernice remembers how she and her husband and two older daughters would laugh and laugh at Sheryl's preternatural act, and talk about "our little rock singer.

"Little did we know," adds Bernice.

There were three pianos in the house, and often all three girls would practice at the same time, with Bernice occasionally calling out "B-flat." The stereo was always on, reflecting the tastes of the various Crow family members, from jazz to big bands to more contemporary '70s singer-songwriters.

Sheryl lived a seemingly idyllic childhood as an attractive, popular girl active in athletics, choir and school plays. Yet she says she always felt as if she was on the periphery of the cool group. And she also was kind of a people-pleaser; it was important for her to win her folks' approval. That mattered most to Sheryl.

The yearbooks that chronicle her four years at Kennett High, from 1977 to 1980, bear out the golden girl image: drum majorette, a member of the Pep Club, Future Farmers of America, and the National Honor Society. She was also Freshman Maid, Senior Maid and the Paperdoll Queen.

Whatever activity she took on, Sheryl threw herself into it with a perfectionist's zeal. She'd endlessly practice her baton twirling in the family's backyard, studying her reflection in the house's big glass window. Marching back and forth for hours, she eventually stomped a dirt path in the grass.

Mizzou Days

Sheryl Crow majored in music education with a concentration in piano at the University of Missouri at Columbia. She pledged the Kappa Alpha Theta sorority. Her goal was to teach music to youngsters.

She studied with Raymond Herbert, a music professor at Mizzou, who had taught her older sister Karen a few years before. Herbert considered Karen exceptionally gifted, both academically and musically.

Sheryl was slightly less exceptional. No question, she was a very good student and musically talented in her own right, but more than that, she was a plugger.

Herbert sensed a fierce determination behind Sheryl's "sweet, delicate" demeanor." At her insistence, he gave her piano selections not only suitable for her current level but also ones that demanded more virtuosity. Sheryl never failed to master those pieces.

But Sheryl Crow's greatest claim to fame occurred outside the classroom. She played and sang in a Top-40 campus band Cashmere, rolling out the covers every weekend for the local frats and sororities: Heart's "Barracuda," Lionel Richie and Diana Ross' "Endless Love," the Doobie Brothers' "China Grove," Nena's "99 Red Balloons."

By all accounts, the band was no great shakes in the creative department, but it got Crow onstage, singing and playing keyboards in front of the public. She liked it up there, and for a few in the audience, it became the first overt sign of her deepening drive to perform.

Even in Cashmere, Crow was always wanting to do more, always talking about doing original songs. Fred Moreadith, Cashmere's drummer, remembers her determination, her always going that extra mile.

But when college came to an end, so did Cashmere. Crow moved to St. Louis, lived in an apartment complex in Webster Groves and worked for several years teaching music at Kellison Elementary School in the Rockwood District in St. Louis County.

At the time, the clean, modern, brightly lit school in Fenton served roughly 700 students in kindergarten through sixth grade. Crow worked as a vocal music teacher, and taught the special chorus for the fifth and sixth grades.

Mary Jackson, a second grade teacher at Kellison, recalls a "hometown girl from a small community, a relatively quiet, strait-laced, nice girl," but never sensed a future rock star in her midst.

Modest Beginnings

Crow's time on stage with Cashmere had lit a fire that hadn't died. In her heart, she didn't want to just teach music -- she wanted to pursue it as a career for herself. An acquaintance suggested she contact Jay Oliver, a St. Louis musician who had made a name for himself as a producer of commercial jingles, industrial themes, corporate music and demos.

Oliver, who now lives in Los Angeles, ran a thriving recording studio in the lower level of his parents' home in Creve Coeur.

Crow called him and he invited her to come by his studio. He remembers "a really sweet, very innocent girl" with effortless charm, good looks, and a brilliant smile. Although Oliver found her to undeveloped as a singer and musically naive in terms of the roots of rock 'n' roll, the two shared a jazz background and immediately hit it off.

Under Oliver's tutelage, Crow threw herself into an intense learning period. Within months, she had improved so rapidly as a vocalist Oliver began using her as a singer on jingles. Her first was a commercial for a back-to-school spot for Famous-Barr.

The local band P.M., which was signed to Warner Bros. for a time, was also auditioning for a female back-up singer. Oliver remembers the hardcore work ethic Crow applied to win the spot: "She took all the tapes home, learned them, the next day came in and kicked a--."

Although Crow enjoyed teaching, she considered her day job a temporary one. She asked Oliver if it was a smart move for her to quit her teaching gig and do music full-time. He said yes. "She was coming along so fast, man, this chick was going somewhere," Oliver said.

She worked eight hours a day for months on nearly every aspect of her craft -- learning her music history, perfecting her voice, performing with P.M., and recording a number of jingles for the likes of McDonald's and Toyota.

During a vacation, Crow visited a friend in Los Angeles who lived about 45 minutes from the city, in Redondo Beach. She was psyched by the sunny, party climate of the West Coast, and talked excitedly of moving there one day.

After a love relationship back in St. Louis soured, Crow decided to make the big move to LA to pursue her music career. She went home on a Tuesday, and told her parents she was leaving on Sunday.

"I just knew that I was going to have to make the leap and pursue the dream, or resign myself to not pursuing it," she says. "I just felt that was such a heavy weight to have to live with, wondering what would have happened."

Jacko And Wackos

In 1986, when Crow was 24, she lit out for Los Angeles, without any cynicism or pre-conceived notions. "At that point in my life I was really not jaded at all," she would later recall, "and was more wide-eyed and full of wonder at the possibilities."

But the city held immediate lessons for the small-town girl. She moved four times in six months, and at least one of the moves served as an eye-opener to the fact that this place wasn't Kennett.

She rented a house from an ad in the newspaper, and wound up living with a couple of strangers. It was a nightmare, her first taste of city girls who did drugs and ran much wilder than Crow. "They were actually nice people," she says, "but I hadn't been exposed to that, and to the fast pace of having people in and out of your house."

She moved into a one-room apartment, 500 bucks a month, a lot of money back then. Matt Collier, a Kennett native and Mizzou graduate who also lived in LA at the time, recalls the first time he visited Crow there. Serious musical equipment was scattered everywhere: keyboards, P.A., synthesizers. He knew at that point there was a heck of a lot of "something" to Crow's music thing.

Just beyond the door of her struggling, anonymous life, Crow could clearly see the great chasm between the haves and the have-nots, the winners and the also-rans. She could look out her apartment window and see Jaguars and Mercedes driving down the road. Huge displays of wealth. And she found it intimidating, as she was going through her money. "That's part of the plight of living in Los Angeles and part of the dues-paying, being bottomed-out and working really hard waiting tables," she says.

Crow might have gone to LA naive, but she was not unprepared. Jay Oliver had helped her put together a professional demo tape, filled with her commercial jingle work. She got a list of all the top session music producers in LA and inundated them with tapes and photos.

It was a pro package, and Crow was relentless in marketing her talent. If people wouldn't take her calls, she'd deliver her tape in person. She finally landed her first studio gig, word spread, and soon she was doing four to five jingle sessions a week.

It was during one such studio session that she overheard that Michael Jackson was auditioning for back-up singers for his upcoming 1987-88 "Bad" world tour. Crow, fueled by that naivete that knew none of the industry rules, crashed the audition and won a slot.

It was a high-visibility gig that took Crow around the world and kept her on stage for 18 months, done up in big blond hair and engaging in several bump-and-grind duets with Jackson every night. It was a gig that also landed her on the cover of the National Enquirer and other tabloids. Among other things, she supposedly was carrying Jackson's love child.

Crow found the spotlight more fearsome than appealing. At home in Kennett, the tabloids were camping out on her parents' front lawn. In LA, they were following Crow everywhere.

But the tour also introduced Crow to the music industry, and opened doors. After it ended, Crow did more session work with Sting, Rod Stewart and Don Henley. She was writing then as well, signed a publishing deal with Warner/Chappell in 1989, and eventually placed songs with the likes of Wynonna Judd while trying to get her own solo career off the ground.

During a back-up recording session, one of Crow's demo tapes made its way to A&M. The major label liked what it heard, and signed her, but the initial sailing was not smooth.

Crow recorded an entire album, but the highly polished pop sound left both Crow and the label cold. The recording was shelved, but Crow was determined to work, and keep on working, until she got it right.

With a recording contract but still no record, Crow started jamming with a group of musicians who hung out at producer Bill Bottrell's funky and homey recording studio in Pasadena. Dubbed the "Tuesday Music Club," or "TMC," the loose gang included the former David & David duo of David Baerwald and David Ricketts, as well as Crow's then-boyfriend, keyboardist Kevin Gilbert.

It was a casual party atmosphere in the studio, with all the musicians trading up instruments and collaborating on jams that began turning into songs. Out of those sessions, Crow emerged with the debut album, "Tuesday Night Music Club," which would eventually introduce her to the world.

`All I Wanna Do . . .'

In 1993, the "Tuesday Night Music Club" album hit the stores, and made its way to radio stations across the country. But it took months before it became a massive hit with the public. Crow hit the road and toured relentlessly; she made a stop at the American Theatre in April 1994, and returned to St. Louis three months later as an opening act on the Eagles' reunion tour stop at Riverport.

As Crow was taking her music on the road and landing a couple of mid-chart radio hits, the music channel VH1 was going through an overhaul. Hoping to shed its dorky, pop-schlock image, the station wanted a hipper look and sound to woo the 25-34 age demographic. And Crow, along with acts like Hootie and the Blowfish, Melissa Etheridge and Des'ree, had just the right mix of funk and easy-listening to get the job done.

It was the woozy, infectious, loose-limbed hippie jam "All I Wanna Do," the first big single off Crow's new album, that struck a mass nerve. With an off-kilter steel guitar lazily winding its way through the strummed guitars and loopy percussion behind her, Crow turned the verses into a seductive, odd rush of talking-blues.

"I like a good beer buzz early in the morning," she sang/talked, and a nation of baby-boomer rock fans grew misty-eyed over a hazy memory made fresh again.

With Crow's tune being played in heavy rotation on VH1, and with radio stations following suit, she became almost ubiquitous. Suddenly, everyone wanted to talk to Crow, to have her on their shows. Not only was she making music people wanted to hear, she also was extremely pretty -- not a bad combination for an ambitious woman rocker.

At home in Los Angeles, not everyone was happy with Crow's new-found success. While members of the Tuesday Music Club received songwriting and session mention on the album, accusations quickly flew that Crow had taken more credit than deserved for the songs, and that she had cut TMC members out of her tour plans.

But it was an appearance on the "Late Show with David Letterman," when Crow performed the song "Leaving Las Vegas" off her debut album, that caused the most controversy. After she was done, Letterman beckoned her over and asked if the song was "autobiographical." She sheepishly said yes, then amended her response to say it was "metaphorical."

She omitted the fact that the song was collaborative, and that the collaboration had been led by TMC member Baerwald. He had based the song on a novel by the same name written by his friend, John O'Brien. (The novel later became the basis for the 1995 movie for which Nicolas Cage won the Academy Award as best actor.)

Angry that Crow had not given others on-air credit, the TMC backlash escalated. O'Brien, a deeply troubled alcoholic, committed suicide shortly after the Letterman show. A number of publications eventually jumped on various aspects of the TMC story, and most made Crow out to look like a selfish, no-talent self-promoter.

The album went on to earn Crow 1995 Grammy awards for best new artist, record of the year and best female pop vocal performance. It should have been a time for Crow to bask in her success. Instead, she nearly went into seclusion -- at least from the press.

"It felt like almost the day after the Grammys, my press really changed," she says. "I went from being the underdog to being the person to be ripped apart. I didn't know how to deal with that. What's really helped me is isolating myself from the whole press thing and actually just not doing very much of it."

Every Day, A Winding Road

Image is nearly everything these days, at least in the world of rock 'n' roll, and currently, there are two distinct images of Sheryl Crow that swirl in the pop consciousness. The first came from her 1994 leap into full-fledged stardom, with Crow's classic rock served up in a funky, rootsy charm.

The second came last year, when Crow re-emerged with her second, self-titled "Sheryl Crow" album. This time, there was a decidedly harder snap to the proceedings, with many of the neo-hippie leanings of her first outing morphing into a far more jagged '70s rock stance. With the piercing if flawed "If It Makes You Happy," Crow wailed over the raw clank and punch of electric guitars. "If it makes you happy/then why the hell are you so sad," she sang. It was a hard, complex shout compared to the loose, boozy strains of "All I wanna do/is have some fun."

Even Crow's look changed. Hippie wear was replaced by high-fashion designer clothes, and her curly locks were straightened and streaked.

Once again, the music -- and ultimately her success -- was obscured by controversy. Before the release of her sophomore album, Kevin Gilbert, the TMC keyboardist and Crow's ex-boyfriend, was found dead, clad in a leather skirt with a strap around his neck, the victim of autoerotic asphyxiation. The news linked back to Crow, and in a story in the San Francisco Chronicle, it appeared that Gilbert never fully recovered from the TMC backlash.

Then came a November 1996 Rolling Stone cover story, with Crow looking her most coquettish clad in hot pants and leather boots. In the commercial rock world, it doesn't get much bigger than the cover of Rolling Stone.

But the story behind the cover wasn't the type of attention that any artist would crave.

"I heard all they wanted to talk about was the Tuesday Night Music Club scandal and all that stuff," she says, claiming that she did not actually read the article but heard about it from friends.

Still another blow came when Crow's second release was banned from the shelves of all Wal-Mart stores. The giant retailer took exception to her song "Love Is A Good Thing," which contained the lyrics "Watch out sister, watch out brother/Watch our children while they kill each other/With a gun they bought at Wal-Mart discount stores."

Despite those setbacks, Crow's second CD has kept her on the radio and before the public. In March this year, she took home two more Grammys for her sophomore release, victories for best rock album and best female rock vocal performance.

A few nights after the Grammy show, she played Boston's Orpheum Theater, to an audience that consisted mostly of thirty- and fortysomethings. The petite Crow, clad in black leather pants and sleeveless shirt, her hair streaked blond, took the stage to rousing cheers. Backed by a five-man band on guitars, bass, drums and keyboards, she launched into the hit "If It Makes You Happy."

Not a showy performer, Crow stayed mostly at the mike and strummed the acoustic guitar slung around her neck. She rarely interacted with her band, and failed to introduce any members.

But her voice, which has yet to be accurately captured on disc and frequently sounds breathy on record, was far more powerful in a live setting, reaching easily into a tough, grainy register.

In between songs, she looked out at the packed house. "Have you had a good week?" she asked. "So have we."

She smiled wide at the cheers. The audience was responding to Crow's Grammy coup.

The Road Ahead

Sheryl Crow, who recently relocated from Los Angeles to New York, is a lot more savvy than when she first ventured out to the West Coast, and a lot more circumspect. She also is at a crossroads, trying to weigh her professional interests with those that are deeply personal.

She believes the things that caused all her relationships to mutiny is the fact that she hasn't been very present in them.

"I've buried myself in my art, and that's been a refuge and also an escape for me a lot," she says. "It's just not an easy thing for [a man] to cope with, having a relationship with a woman who's not conventional in any way."

On one hand, Crow mentions seeing herself having children and raising them in a small town someday, a town just like Kennett. On the other hand, she speaks of adoption, something she's currently looking into. But mostly, it seems that Crow grapples with that peculiarly female dilemma -- being a working woman who wonders if a family is even in the cards.

"I've gotten to the point now where I'm looking at my life and trying to accept that I may never have kids," she says. "I may never get married. I've had some wonderful relationships, and I've had the luxury of being in love a lot. So I can't say that I've led an extremely lonely life. It's just the choices I've made, it's sort of eliminated my having a normal life. But it's been an even trade-off."

And that trade-off is the rock stardom that has kept her at the center of the public eye for the last several years.

"Now it's about success, and the size of your success," Crow says, and in many respects, she is right. The pressure in today's music business is enormous. There was a time when selling a million records was considered a stratospheric achievement in the recording industry. And musicians -- buoyed by A&R (artist and repertoire) folks who signed artists with career longevity in mind -- were allowed to develop their music over a series of albums.

In today's music biz, disposability rules, and the scenarios have grown outlandish. Bands today are signed promiscuously and at break-neck speed. Artists are expected to hit quickly, and hit big. If they do not, the descent is hard, fast and uncompromising.

Crow refers to these extremes as "the nature of the beast." In many ways, she has come to the fore at a time when the music industry is, in every respect, at an all-time low.

"The thing that's discouraging is the way the music industry has gone now, since I've been in it. There's no developing of young artists, there's no having five or six albums to define who you are," she says. "You have your one opportunity, or maybe two, before your record label drops you."

As Crow talks about that past, her voice takes on the awe of the Kennett kid, a rock star remembering a simpler time when she was simply a rock fan. A lot has changed in the rock world since the days when Kennett kids did their own thing by making music: the loss of a nurturing community, the lack of artist development, the accelerated nature of a business which voraciously exploits trends, then just as quickly disposes of them for the next flavor of the month.

"There's so much pressure and so much weight on chart positions and on sales," she says. "It's created a really competitive environment amongst musicians."

For Crow, who has scaled the heights into contemporary celebrity, there are few peers now in life who know exactly what it is that she is going through.

It's little wonder, then, that she speaks so affectionately about the town from which she came. It's easy to understand what she misses about it, what it continues to offer her no matter where she goes. In a big world of raw, ultimate exposure, it is in Kennett, a small dot at the edge of the state, a town tucked into the heel of the boot, where Crow finds that which eludes her so often now on the bruising stage of fame: unconditional love, ramrod loyalty, genuine respect.