Sheryl Crow Got Into Prank Wars With Michael Jackson

Sheryl Crow became one of the biggest legends of the music world in this day and age. Everyone has a different path to success, and hers certainly proves that she worked to earn everything that she got. Her humble beginnings brought her to ultimate stardom – but unlike many others in the music industry, she didn’t let it get to her head.

She rose to stardom, though the game of life didn’t fail to send obstacles her way. She dealt with disappointing lovers, deadly diseases, and harassment from managers claiming her success as something she owed them for. Sheryl Crow is successful because she had a goal and worked to accomplish it!

Sheryl Crow Started Small, but Made It Big

Sheryl Crow’s humble beginnings make her such a relatable musician! She broke into the music scene in the early 1990s, and her lyrics have proven to be timeless. Her hit songs still ring true today, with her biggest fans knowing deep down inside that her lyrics truly came from the heart.

Her humble beginnings not only inspired her to write songs that are the epitome of female strength and empowerment but even inspired her to adopt two children and live life as single mom. Sheryl Crow’s path to success shows that once she set a goal, she did whatever she needed to in order to attain it!

Sheryl Crow’s Early Days

Sheryl Suzanne Crow was born in Kennett, Missouri on February 11th, 1962. Her parents Wendell and Bernice were ecstatic to welcome another daughter to their family roster. She is a middle child – the third born in her family, following two older sisters, Kathy and Karen. After Sheryl’s birth, her family continued to grow.

After Sheryl was the baby of the family, her younger brother Steve. Her parents were happy with their four great kids, and they lived a simple life in Missouri. The musician started playing piano when she was only six years old.

Her Music Education Started at Home

Crow was raised in a small farming town in Missouri, to parents who both taught different types of music. Her mother worked as a piano teacher, introducing her daughter to what would end up being her life’s work. Her father was also a practicing lawyer, but taught trumpet lessons on the side.

Her parents taught her to share her gifts with those around her. She was raised to believe that knowledge is power, and that sharing knowledge with others would only do great things for the world she lived in. She went on to study music and related fields in her academic career.

She Studied Music at the University of Missouri

Crow studied music performance, composition, and education at the University of Missouri in Columbia, Missouri. She sang in a local band called Cashmere during her university days and was pretty active beyond that on campus.

Crow was a member of the Kappa Alpha Theta sorority on campus, as well as Sigma Alpha Iota, the international music fraternity for women. She was known for her involvement on campus, and even worked as a “Summer Welcome” orientation leader, helping new students find their footing.

How Old Is Sheryl Crow?

Sheryl Crow was born on February 11th, 1962, making her 59 years old. She’s got years of experience as a musician under her belt, which certainly comes with a ton of stories. She’s an Aquarius, meaning that she is a woman who marches to the beat of her own drum. If anyone is calling the shots in her life, it’s her!

Her star sign seems to be a spot-on fit. Aquarius women are known for requiring the freedom to be who they really are and thinking and acting independently. If that’s not a perfect description of this strong female star, then what is?

She Started as an Elementary School Music Teacher

After settling in Fenton, Missouri after graduating from college, Crow accepted a job as a music teacher in a local elementary school. Imagine being one of her students at Kellison Elementary School, hearing that your former music teacher became a famous musician?

Crow worked as a music teacher at the St. Louis area elementary school for two years. She used her music education degree to empower the next generation of musicians. If she had been my music teacher, I’d have shown up every day!

Her Teaching Days Were Short Lived

Crow spent two years teaching at a local elementary school but knew that was not the path she was destined to take. She spent weekends singing with Cashmere, along with other local bands, and ultimately decided that staying in education was not the right move for her. She was ready for something more.

Crow knew that staying in education wouldn’t help her accomplish her goals of working as a musician professionally, so she packed her bags and took her country girl self out to Los Angeles. She was finally able to start pursuing her dreams, and the City of Angels was the perfect place to get started.

She Started Singing Jingles

Before heading out to Los Angeles, the star was introduced to a local St. Louis musician and producer, Jay Oliver. He had a basement recording studio at his parents’ home and brought her in to start recording jingles. Her first jingle was for a back-to-school spot for a famous St. Louis department store.

The store, Famous-Barr, is no longer in business. However, not everything went south for the department store; it initially went defunct in 2006 but was soon acquired by Macy’s. Fortunately, not every jingle she sang was for companies that went out of business. She sang for McDonald’s and Toyota, as well!

Is Sheryl Crow Married?

Sheryl Crow has never been married. She’s a strong, independent woman, but that doesn’t mean she doesn’t want some companionship! She has just learned that she doesn’t need it to be happy. She has a long list of ex-boyfriends – which we’ll get to, just sit tight – but, no, she is not married.

She was, however, engaged for a period of time to cyclist Lance Armstrong. The two became engaged in September 2005, though the relationship unfortunately did not last. The two called it quits and broke off their engagement and officially split by February 2006. She dodged a bullet there.

The $40,000 Jingle

In her 2013 interview with a music critic from The New York Times, she opened up about the weekend gigs that she’d done – weddings, bat mitzvahs, and so on. At one of these gigs, she was introduced her to a local industry professional who helped her get some important gigs.

One commercial she sang for did incredibly well. It started out as a regional jingle, reaching as far north as Chicago, but ended up doing way more than that. It went to network, and made her $40,000, which went straight to her savings. That lucky commercial was for McDonalds, and it gave her the push she needed to get out to Los Angeles.

Her Earliest Days in Los Angeles

After finding some success with her jingles, she knew she wanted to use her voice for more than just smaller performances. She gave notice at work, saw her parents on a Tuesday and let them know that she was leaving the following Sunday for her new life in the City of Angels. She was destined to make it.

She got into Los Angeles at 4:30 p.m. after driving all night from Missouri. She found herself ready to tackle the city – but not before dealing with the infamous traffic Los Angeles is known for! She had her jingles ready on cassette tapes to be given to any industry professional who would hear her out.

The Typical Hollywood Origin Story

Make no mistake – there’s no standard path to success. However, you can definitely tell that so many stars start out working as waiters and waitresses to pay the bills and continue to audition. Crow joined the ranks and went to every audition she possibly could.

She found her big break as a backup singer for several world-renowned artists. From 1987 to 1988, she was a backup singer on Michael Jackson’s famous “Bad” World Tour. She went on to tour as a backup singer for artists like Don Henley, Rod Stewart, Sting, and George Harrison.

Funny Business With Michael Jackson

The King of Pop, Michael Jackson, had Crow working as a backup singer on one of his world tours. The two had quick-change tents that were adjacent to each other, and the superstar wanted to be playful with his backup singer who was just next door.

With just a wall between their changing compartments, Michael Jackson used to throw grapes, carrots, and other tiny snacks over the wall at her. Crow even said that she would hear him giggling at his own pranks! Nothing takes the stress out of a situation like making a joke about it!

Sheryl Crow Had Fond Memories of Michael Jackson

In addition to his food-fighting pranks, Crow had other fond memories of the King of Pop. She recalled how much he loved to laugh, and that he would often rent out entire amusement parks for him and his employees’ entertainment. Her favorite memory of him was watching him perform his song “Human Nature.”

“There was something so genuinely vulnerable in his voice on that song and watching the freedom with which he danced, doing the moves he invented only made me more keenly aware of the greatness I was blessed to be witnessing.” She channeled his energy into her own successful career.

Her Late Ex-Lover, Kevin Gilbert

Crow used to date Kevin Gilbert, a musician who she joined in the group Tuesday Night Music Club. Gilbert died in 1996 by autoerotic asphyxiation, which came as a shock to many who knew him. But no one linked his death to Crow. Actually, Crow wasn’t one of the people who was shocked by the news of his death. “In the weirdest way, my reaction was that of not being surprised,” Crow said.

“As long as I’ve known him, he’s struggled with life, as if every single event in life was out to bring him down or trip him up.”  Crow’s song, Sad, Sad World, might just be her farewell note. Her lyrics: “I know you hate me, I see that now . . . I’m a bad, bad girl for letting you down/I remember every f***ed-up minute/It’s a sad, sad world without you around.” She and Gilbert dated in 1992 and evidently, didn’t go as planned.

Her First Album Was Unreleased

In 1992, Crow recorded her first attempt at an album. She did so along with the help of Sting’s record producer, Hugh Padgham. The album was self-titled and was set to be released in September 1992, but after some thought and discussion, Crow and her label decided the album would not be released.

She was signed to A&M Records, and both the record company as well as the artist herself felt the album felt “too slick.” Now, she’s leaving her fans to speculate about what masterpieces she might have held back, but it seems like we will never know!

Her Debut Album Resulted in Multiple Grammy Wins

Sheryl Crow worked her way to success after that initial unreleased album and found herself as truly the next big thing. Later in her career, she would win nine Grammy awards and be nominated a whopping 31 times! That’s quite an accomplishment, we’d say – but that’s not the craziest part.

The wildest part here is that her 1993 debut album, “Tuesday Night Music Club,” helped her earn her first three Grammys! That’s right – her first album won her the most coveted awards in music history. She won recognition as Best New Artist following the release of this album.

She’s Got Lots of Grammys!

1994, not long after her first album was released, was a great year for Sheryl at the Grammys. She won the Grammy for Best New Artist, Best Female Pop Vocal Performance, and Record of the Year for her hit song, “All I Wanna Do.” The only upset there was losing out on her Song of the Year nomination.

Just a couple of years later, she won the Grammy for Best Rock Album for “Sheryl Crow,” the album that held another one of her hit songs, “If It Makes You Happy.” This song also won a Grammy! All in all, she was nominated for 32 Grammys and taking home nine of them. She’s been recognized by the best of the best!

She Suffers From Sleep Paralysis

Sleep paralysis is scary; being fully conscious yet unable to move is a truly horrifying thought. Researchers believe that it is caused by a disturbance in the rapid eye movement cycle, better known as REM sleep, and usually happens as people are either falling into or coming out of this kind of sleep cycle.

This stage usually ends up with the brain paralyzing the muscles, because the brain needs to make sure the rest of the body doesn’t try to act out the dreams it is having. As a result, whether someone is fully awake or only half awake, they know that their body cannot move while suffering from this phenomenon. Sheryl spoke out about her experiences with it.

The Rolling Stone Interview That Exposed It All

In an emotional interview with the magazine Rolling Stone, Crow opened up about her struggles with sleep paralysis. Things got so bad that she was even afraid to go to sleep. She was terrified of the state that it put her in, and she was uncomfortable with how it made her feel.

Here’s an extra level of terrifying for you to sink your teeth into: Sometimes sleep paralysis comes with auditory or visual hallucinations. She and her mother share the same condition, though she wishes it weren’t part of her life. Many folks who believe in the paranormal will claim to experience the condition when interacting with demons and ghosts from the great beyond.

She’s Quite Short

Crow stands somewhere between 5’1″ and 5’3″, which is pretty tiny! Regardless of her exact height, you might not be able to tell this from photos of her. She appears to be taller – many people think from her public appearances that she’s somewhere around 5’7″, but she’s far from it.

She’s also quite familiar with these handy devices for her feet that make her taller. That’s right – we’re talking about high heels! For years, Crow has managed to come across as taller than she actually is partially because of her high heels, and partially because she’s so fit!

She Beat Breast Cancer

Cancer is a horrifying diagnosis for anyone, and breast cancer is no different in this case. Though there are variants of the disease, all typically pretty invasive, the survival rate is shockingly high for breast cancer. This is great, especially because no one should have their life cut short by a disease like cancer, though unfortunately many do.

One of the brave survivors of breast cancer is Sheryl Crow herself. Luckily for her, she caught it while it was still in the early stages. According to an ABC News report from 2006, she underwent a lumpectomy, what she described as a “minimally invasive surgery,” as well as seven weeks of radiation.

The Diagnosis Shocked Her

Crow was beyond shocked when she learned that she had breast cancer. Who wouldn’t be? She was always healthy as a young woman and the disease didn’t run on either side of her family. The diagnosis opened her eyes to what stress can do to a person.

Crow defines herself as a fighter, and she will remain that way until the day she dies. Luckily, beating cancer allowed the rest of the world to keep enjoying her work. She made waves across the world, and across the music industry, and we are beyond grateful to have her around to this day!

She Adopted Two Sons as a Single Mom

Becoming a parent is a life-changing experience, whether you’re famous or not! Sheryl Crow knows this firsthand, as she took a leap of faith and adopted two sons, one in 2007 and one in 2010. “Adopting my boys — that’s just been the biggest everlasting event that has informed everything, and really for the better.”

In an interview with People, she opened up about how surviving breast cancer changed her perspective. “Being diagnosed with [breast] cancer was a showstopper, for sure. I think it dictated that I reevaluate my life and set up new guidelines for the way I want to live,” the musician said.

She’s a Proud Momma

She’s a proud mother to her two sons, Wyatt and Levi. After she finished promoting her 2013 album “Feels Like Home,” she had an epiphany about how she wanted to spend her time. She knew that something had to change if she wanted to dedicate her time to being a mom.

“I didn’t want to spend any more nights away from home. When you have kids, your priorities definitely change. I really felt consistency is the most important thing,” Crow stated in an interview. She felt she needed this big shift in her life, and she was more committed to motherhood than ever.

She Doesn’t Let Her Sons Get Addicted to Technology

In this day and age, we all know that most people are completely and utterly addicted to technology. So many people, across different age brackets, suffer from technology addiction, because it’s hard to live in such a high-tech world without engaging in the culture! Well, Sheryl won’t let that be the case for her sons.

Some of her newer songs over the last couple of years have been influenced by society’s dependence on technology and social media. “I’m very protective of them being allowed to have the innocence of being children. They don’t have iPhones, they don’t have TVs in their room, and we have a 30-minute rule: 30 minutes of screen, either the TV or the iPad, and that’s it,” she shared.

She’s Making Efforts to Protect Her Boys From Addictive Technologies

“When Wyatt was really little and we would be flying, we had educational games on the iPad, and he learned his letters and numbers and all that — but what really happens?” she says. “He’s learning things, but also his brain is becoming like a little sponge for those bright colors and those quick edits, and what it winds up doing is it creates this addiction. It’s crazy,” she stated.

She continued, “It’s easier for a parent to say, ‘Ugh, let them sit on the iPad, I’ve got things I need to do.’ And I feel that way sometimes: ‘I just need an hour to myself, here’s your iPad.’ But I know that it’s like giving a hit off a crack pipe, and then saying, ‘How did you wind up being addicted to crack?!'”

She’s Got a Lengthy List of Ex-Boyfriends

Crow has a long list of famous exes – she’s gorgeous and talented, who wouldn’t want to snag her? She’s highly coveted and has proven time and time again that she’s a strong, independent woman who does not need or want to be tied up by a man who doesn’t deserve her.

Being a strong, independent woman doesn’t mean that she can’t give herself a shot at love, though! She’s dated some of the most coveted (and controversial) celebrities over her years and has even teamed up with some of them for albums. They were lucky to have her!

She Dated a Much Older Man, Eric Clapton

Back in the late 1990s, Sheryl Crow dated legendary musician Eric Clapton. He just so happens to be a full 17 years older than her! The relationship was relatively short-lived, though he is said to be the inspiration for one of her greatest hits, “My Favorite Mistake.”

This song is about a womanizing ex-boyfriend, leaving room for speculation from her fans. Who could it be about and did the relationship end so badly that she had to take it out on him in a song? Well, we may never know – unless, of course, we end up being the next one of her lovers and get the inside scoop!

She Never Admitted Who the Song Was About, but Had Him Join a Performance

Crow has never quite confirmed who that song is about, and she has certainly appeared to move on from her former romance. When Clapton joined her 1999 performance in New York City’s Central Park, she clearly defined their relationship.

She introduced Clapton as “a really good friend of mine,” and things did not stop there. They seem to remain friends to this day, and he even appeared on her last album, Threads. This leads us to believe that their friendship is stronger than ever, even with their romantic history!

She Dated Owen Wilson

Back in 1999, Crow began dating actor Owen Wilson. The two met on the set of a film that isn’t super well-known, The Minus Man, where Crow made her film debut. She played one of Wilson’s serial killer character’s victims – what a great way to start out a relationship!

Wilson and Crow dated seriously for two years. They made several public appearances at coveted events, like the world-famous Vanity Fair Oscar Party in 2000, and she later admitted that her song “Safe and Sound” from her 2002 album, C’mon, C’mon, was dedicated to him.

She Dated Actor Josh Charles

Their relationship wasn’t the longest she’s had, but at least she gave it a try. Crow dated The Good Wife star Josh Charles and brought him as her date to the Grammy awards the following February. Public appearances together only cause the rumor mill to turn rapidly!

Unfortunately, by April of that same year, the two ended their short-lived relationship. A source told Us Weekly that “they are no longer seeing each other. She’s looking for The Guy, and he wasn’t it.” Not every relationship is going to last a lifetime, Crow’s relationship with Josh Charles included!

Her Relationship With a Disgraced Athlete

Sheryl Crow’s highest-profile relationship was with the infamous cyclist, Lance Armstrong. The two met at a charity event in 2003, not long after he had divorced his wife (and the mother of his three children), Kristin Richards. Their relationship was serious enough for him to pop the question.

Crow revealed secrets about illegal activity that he committed while they were together. While they were dating, he got an illegal blood transfusion right in front of her, back in 2004. She reportedly willingly handed over that information to the FDA, though Armstrong assumed she wouldn’t do a thing with that information.

They Had a Good Time Together

This couple was made up of two highly coveted celebrities who both worked a ton. It’s a wonder that they even made time for a relationship! She would often be seen on the sidelines of his races, cheering him onto victory. He also joined her at red carpet events for the music industry.

“I mean, we really loved each other a lot and still love each other a lot,” she told Good Morning America back in 2008. Armstrong was even the inspiration for not one, but two of her albums! The relationship must have been great if he inspired multiple albums!

The Beginning of the End for Crow and Armstrong

Armstrong and Crow were together for three years and got engaged in 2005. Unfortunately, the relationship ended after being engaged for five months and living on a ranch together. Armstrong opened up about the end of their relationship in his book, Lance. Some relationships just aren’t meant to last forever, it seems!

“She wanted marriage, she wanted children; and not that I didn’t want that, but I didn’t want that at that time because I had just gotten out of a marriage, I’d just had kids,” Armstrong said when asked about why things ended. That’s not all, though… there’s more.

She Went Quiet After Their Breakup

Crow went under the radar after their breakup but did make a clarification on an appearance on Good Morning America not long after. He claimed it was about kids, but she said that wasn’t the case by any means. They just wanted different things – there’s nothing wrong with it, but it’s still a bummer.

“It’s about what he wants and it’s about what I want. And where the two don’t meet, there’s definitely a, you know, a fissure.” Including Armstrong, Crow has had three engagements broken off. She’s still open to marriage, though it doesn’t seem to be a priority for her.

Motherhood Gave Her Insight Into Her Relationships

Despite multiple relationships going down the drain, Crow is still open to marriage. In 2019, she told People that she’s still open to marriage, even if her previous three engagements never came to fruition. She credits motherhood with keeping her open to making that kind of commitment.

“Being well-loved and loving someone is what it’s about,” the singer said. “And that’s another area that’s just priceless to be able to model to your kids. So, if it isn’t that, then I don’t want it around them.” Motherhood is a gift, and she won’t let any relationship change her views on that!

She Dated TV Personality Ryan Seacrest

Ryan Seacrest is known as a TV personality for the ages. He’s also known as one of Sheryl Crow’s many exes! The same year that he briefly dated Teri Hatcher, back in 2006, he followed that relationship with some intimate time with Crow. It may have been short, but it was a relationship nonetheless!

Seacrest has become one of the most recognizable faces in entertainment to this day. It’s no wonder that he might have been linked to another incredibly accomplished entertainer like Crow! Their relationship didn’t last very long, but it’s interesting to speculate about!

She Dated a Longtime Friend

She enlisted Doyle Bramhall II as the producer of her 2010 album, “100 Miles from Memphis,” and then things got private between the two. They started a relationship and made their first public appearance together at The Society of Memorial Sloan Kettering Cancer Center’s 2011 Spring Ball.

In her interview with Prevention Magazine in May 2011, she opened up about her relationship with a producer (that she kept anonymous). She told the publication that he was great with her kids, and she really appreciated that. It was important to her as a mom to have someone her sons could get along with.

She Didn’t Want Her Sons to Hurt If There Was a Breakup

“I’ve been involved with people and their kids, and if the relationship doesn’t work out, it’s heartbreak,” the musician told Prevention Magazine. She now had people in her life that would be impacted by her relationships and decisions, and she needed to be mindful of that.

She continued, “So I’m keeping the relationship friend-based when we’re around the kids. Luckily, we have a great foundation, having known each other for fifteen years.” At least she understands the difference and separation between the two. Hopefully, she finds love that lasts someday!