Sheryl Crow on Monkeying Around With Michael Jackson’s Chimp and Surviving Sexual Harassment Before the #MeToo Movement

Legendary singer, songwriter, and recording artist Sheryl Crow returned to the Stern Show on Wednesday where she wowed listeners with a two-song concert and opened up about her fascinating life and career. Sitting down with Howard just a few days ahead of the release of “Sheryl,” her career-spanning rock documentary, the 60-year-old luminary was happy to reflect on many of the more incredible moments from her storied career, whether it was watching TV with Michael Jackson and his chimp or throwing up before throwing down with the Rolling Stones on stage.

Crow, who has 9 Grammys to her name and has sold over 50 million records, also spoke candidly about her legacy as a rock star and crossover artist. Her visit to the show coincided with the unveiling of the 2022 class of Rock and Roll Hall of Famers (which includes female recording legends Dolly Parton, Carly Simon, and Pat Benatar, among others). Sheryl, who has been eligible for a Rock Hall induction of her own since 2019, has not yet been nominated.

Howard wondered if she felt at all snubbed or insulted by having not yet made the cut.

“I feel like I was always kind of an outsider and [by] having songs like ‘All I Wanna Do’ and ‘Soak Up the Sun’ define me, so many people wrote me off,” Crow said, explaining that fundamental misunderstanding about her music and backstory ultimately became a driving force behind her decision to collaborate with director Amy Scott on “Sheryl.”

“When they came to me and said do you want to do a documentary, I said only if the story of the person is told and not the rehash of the awards and … all that stuff,” she recounted. “I was 30 before my first record came out, and I had real jobs—I was a schoolteacher, I waited tables for years and years. There is a whole life there that isn’t just ‘All I Wanna Do’ and happy songs.”

“Those songs aren’t the ones that define your career anyway. Those are just the ones that are ear candy,” she continued. “The ones you write that never get heard are the ones that tell the story.”

Participating in the doc proved to be a double-edged sword. “Sitting and being interviewed for hours on end and recalling all this stuff and recalling the harshness—in some situations—was so draining,” she told Howard. “Also, it was liberating, in a weird way to finally talk about it. A lot of this stuff I’ve never ever talked about.”

One such story involved watching old sitcoms with Michael Jackson and his misbehaving chimp.

It was the late ‘80s and she was a backup singer on the King of Pop’s “Bad” tour. One night, he invited her to his room to watch TV with Bubbles the chimpanzee. Michael was apparently poking him to try and get him in line. “This poor little chimpanzee that could’ve picked him up and thrown him out the window,” Sheryl recalled.

“I’m just trying to, like, stay in my body because Michael is laughing at ‘Amos ‘n’ Andy’ and throwing popcorn and poking Bubbles in the chest, and I’m just this girl who just moved to L.A. seven months ago and used to be a schoolteacher,” she continued. “It’s so weird.”

A Bad ‘Bad’ Tour

A far more serious story from her days on the “Bad” tour involved Sheryl getting sexually harassed by Jackson’s then-manager, Frank DiLeo. She told Howard the experience soured her on the industry.

“I was pretty disappointed,” she said. “You work hard, you’re a nice person, put one foot in front of the other … I thought good things would happen.”

With unfounded rumors about Sheryl and Michael in the tabloids stirring around — “[I] got paid $2 million to have his baby,” she joked of one rumor – the singer found herself part of a machine she wanted no part of.

“There’s a whole backstory to that with having his manager take that notoriety that I was accruing and, you know, trying to architect some pop career around me and I didn’t want to be a pop star,” she explained. “And then the sexual harassment was involved in all of that and then the threat of ‘You’re never going to work’ and my going home and putting bands together and playing my music and having everybody in the industry say, ‘Well, we don’t know what to do with the blue-eyed soul singer … I got a ton of excuses and I just felt like it was all tied together.

Once the tour money ran out, Sheryl took up waitressing again. “It was tough, it was really tough,” she admitted. “I mean, it’s tough coming off the road and just sinking back into your own life no matter what, but that was some other kind of tough.”

Sympathy for the Digestive System

Sheryl has a decades-long relationship with the Rolling Stones, having both performed with the iconic rockers on stage and collaborated with them in the recording studio. She’s even built a lasting friendship with frontman Mick Jagger and guitarist Keith Richards.

When Crow was first starting out, the music scene was dominated by grunge and alternative rock acts. “I was just an outsider, and it was the Stones who kind of plucked me out of [that] and said, ‘Hey, welcome to our scene,’” she recalled. “That was the scene I kind of always wanted to be in anyway. It always felt like I was born too late.”

As warm a welcome as the Stones gave her, Crow was a nervous wreck before first performing with them on stage. “I vomited all day. I was so terrified,” she told Howard. “Right before I went out, [their saxophonist] Bobby Keys … handed me a bottle of tequila and said, ‘here’s a little courage,’ and kind of shuffled me out.”

“I can remember exactly what I was thinking when I was like six inches from Mick’s face,” she added. “‘Oh, this is the guy whose zipper … I unzipped on that record [‘Sticky Fingers’].”

She’s since become a superstar in her own right, of course, but Sheryl said she still gets giddy when she talks with Jagger. “I texted him recently and asked him if he would play harp on [a cover of the Rolling Stones song] ‘Live With Me,’” she said. “As I was texting him, I was just thinking, ‘Oh God, I can’t even believe I have his phone number.’”

On Dating Musicians and the Mystery Man Behind ‘My Favorite Mistake’

Despite speaking for the first time about several different subjects in her new documentary, Sheryl came into the studio on Wednesday still holding on to one big secret: which former partner was she singing about in her sizzling 1998 single “My Favorite Mistake”?

“It’s about Warren Beatty,” Sheryl told Howard with a laugh, poking fun at the long-standing rumor Carly Simon’s classic takedown track “You’re So Vain” was perhaps about the “Dick Tracy” actor, whom she dated in the early 1970s.

Howard pressed on, but Sheryl remained coy.

“I couldn’t reveal that … [but] I’ll give you the scenario,” Sheryl responded. “When I first met this person he was with somebody at a radio event. Then, before we left, I saw him making out with another famous girl—one was an actress, one was a singer—and I was like, ‘That’s so gross.’”

“And then what happens?” she continued. “Much later on, we wind up on a handful of gigs together, and I get sucked in.”

“You couldn’t help yourself!” Howard said.

“You love who you love who you love,” Sheryl responded, quoting rocker John Mayer. “I felt bad about [the ‘mistake’] for 8 or 10 months, and then I never thought about it again.”

Considering Crow has famously dated guitar legend Eric Clapton in addition, perhaps, to her musically inclined “mistake,” Howard wondered if she had a thing for musicians.

“No, I like funny people … I’ve dated famous people, I’ve dated athletes, I’ve dated not-famous people,” Sheryl said, explaining she’s at a point in her life now where she’s ready to make a few more mistakes. “It’s an open opportunity for anyone to be in the category of my next ‘favorite mistake,’” she laughed.

Relationship Changes That Did Her Good

Mick and Keith aren’t the only titans of rock who bent over backward to collaborate with Crow. The one and only Prince was also eager to work with her after first hearing “Everyday Is a Winding Road.”

“These men go absolutely berserk for you. They do,” Howard noted.

“Because I’m hot. Even at 60, I’m hot,” Sheryl said with a smile. “How am I not married? How is that?”

Though she’s never been married, Crow has been engaged on three different occasions. Her ex-fiancés run the gamut from a musician who put religion first to cyclist Lance Armstrong, whose career-altering doping scandal broke while the two were dating. As Howard heard it, it was then, at his lowest moment, that the embattled athlete popped the question.

“That’s happened twice,” Sheryl told him. “I’m always like, ‘Don’t wait until the relationship is over to ask me to get married because you don’t want me to go.’”

Even so, she assured listeners she isn’t holding any grudges. “Everybody eventually grows up and figures out who they are. I give people a lot of leeway if they evolve,” she concluded.

‘Leaving Las Vegas’

The first song Sheryl and her band performed Wednesday morning was a soulful rendition of her classic 1994 single “Leaving Las Vegas,” hailing from her seven-times-platinum debut album “Tuesday Night Music Club.”

“Wow, I love that version of that song,” Howard applauded.

“That felt good,” Sheryl said before adding, “Let’s play a whole set.”

While Sheryl and her band didn’t wind up performing an entire set, she and her backup singers did regale listeners with some extra vocalizations which were so impressive they emboldened Howard to sing along.

Sheryl tried to keep her feedback constructive. “Just stick with what you do,” she told Howard with a laugh.

‘Live With Me’

Armed with a reissue of her first guitar, a ’59 Telecaster she picked at least partially because it’s also favored by Keith Richards, Sheryl geared up to play “Live With Me,” by his band the Rolling Stones. In addition to the track appearing on the soundtrack of her documentary, it also has ties to when she first linked up with them for a gig in 1994.“

When Mick called me to set up the scenario, I hadn’t really exploded yet but there was a big buzz and I was getting played a ton in Colorado and then a ton in France,” she remembered. “I was in France, and he called in the middle of the night.”

Though Mick suggested one song, when Sheryl got to the show Richards had other ideas. “I get over there and I see Keith and Keith’s like, ‘Hey little sister, so you’re going to do “Live With Me?”’ and I was like, ‘Sure,” she recalled. “I just have this incredible memory of being thrown into the big boys club, the real rock star circus.”