New Sheryl Crow documentary to detail Michael Jackson tour, breast cancer diagnosis and past romances

The legendary Sheryl Crow appears in her first-ever documentary for a candid reflection on her incredible journey as a bestselling musical artist

Sheryl Crow documentary to detail Michael Jackson tour, breast cancer diagnosis and past romances
(Image credit: Getty)

American music fans, clear your evening plans—a new Sheryl Crow documentary is about to drop. 

The 90-minute-long film will see the US musician 'remembering, reflecting, and revisiting' memories of her incredible life, in celebration of her outstanding contribution to the entertainment industry as she marks her 60th year. 

Directed by Amy Scott for Showtime, 'Sheryl' promises viewers a candid insight into Ms. Crow's career highs and showbiz lows—as well as the personal, and often extremely painful, struggles that played out backstage. 

Interviews with people close to Sheryl, including Keith Richards, Jason Isbell, and Laura Dern, will also feature. 

Speaking on the recent Television Critics Association panel, the All I Wanna Do singer admitted that she wasn't initially keen to do a documentary—but had a change of heart after her manager sold the idea to her. 

"I’ve always felt like documentaries were told after someone has already gone, or after a fiery plane crash," she said during the virtual interview. "But it was my manager, who has been with me from the very beginning, which is 30 years now, who said, ‘Look, you have a powerful story. You have seen your business change. You have grown up most of your life in the world of music. You have a story to tell and it's time for you to tell that story.'" 

What can you expect from the Sheryl Crow documentary?

'Sheryl' is packed with thought-provoking revelations, offering the starlet's loyal fans a whole new perspective on her amazing life. 

The Soak Up the Sun singer rehashes multiple chapters from her successful career—a notable one being her experience as a backing vocalist on Michael Jackson's Bad tour in 1987. The gig is often credited for skyrocketing Sheryl onto the music scene, but her memory of the job has since been tainted by the child sexual abuse allegations against the late King of Pop. 

“I was naïve," she said, "but I still thought it was weird that there were a couple of little boys on the tour with him. It makes me sad for the life he had and obviously sad for the children.” 

She also alleges that she was subject to sexual harassment from Michael's former manager, Frank DiLeo, during this two-year-long placement. 

Sheryl's breast cancer diagnosis in 2006, which came shortly after her breakup with cyclist Lance Armstrong, is another emotional ordeal explored in the documentary. She recalls the paparazzi's relentless chase to photograph her during her medical treatment, adding, "The craving to see pictures of me at my worst... I felt like I didn’t deserve it."

Sheryl's friendship with Bob Dylan, from whom she sought help when she was battling writer's block, is also discussed in the film. She recalls how she rang him for advice after eight months of struggling to finish her album, only to learn that the US music legend couldn't exactly relate to her plight. When she asked him if he'd ever experienced such a creative drought, he apparently, replied, "No, never!" 

'Sheryl' premieres at 9pm EST on May 6, on Showtime Now.

Emma is a news writer for woman&home and My Imperfect Life. She covers the Royal Family and the entertainment world, as well as the occasional health or lifestyle story. When she's not reporting on the British monarchy and A-list celebs, you can find her whipping up vegan treats and running the roads to cheesy '90s pop music...but not at the same time, obviously.