Sheryl Crow's Grammy Dress From 2005 Ruffled Feathers

Aug 13, 2021

Sheryl Crow is an American musician, singer, and songwriter who is best known for her hit song "All I Wanna Do" and her rendition of "The First Cut is the Deepest." Crow has had an incredible career. She went from working as a backup singer for Michael Jackson in the late 1980s to earning herself nine Grammy Awards out of 32 total nominations. The artist's look she wore to the Grammys in 2005 was so stunning that people are still talking about it today.

Crow was born and raised in Kennett, Missouri. She is the daughter of a piano teacher named Bernice and a lawyer and trumpet player named Wendell Wyatt Crow. She attended Kennett High School and went on to graduate from the University of Missouri in 1984 with a Bachelor's degree in music education. After college, Crow worked as a music teacher at Kellison Elementary School in Fenton, Missouri.

Before touring with Michael Jackson from 1987 to 1989, Crow's first recording job was singing in advertisement jingles. The star would then go on to sell more than 50 million albums worldwide during her career. Crow has established herself as a household name. She even sang the theme song for the James Bond film "Tomorrow Never Dies." 

Crow has had success as an actress as well as a singer, appearing on the series "30 Rock," "One Tree Hill," and "NCIS: New Orleans." The artist is still releasing and performing music today, often posting about upcoming shows on her Instagram account. Keep reading to hear more about Crow and to see the incredible dress she wore to the Grammys. 

In 1993, Crow was dating fellow musician Kevin Gilbert who introduced her to a group of musical artists that met every Tuesday at producer Bill Bottrell's studio in Pasadena, California. Bottrell later agreed to produce a record for Crow that would be called "Tuesday Night Music Club." The record received little success until the release of the third single in April 1994, which was called "All I Wanna Do." It was surprising to Crow because she hadn't initially wanted the song on the album. She said to The Independent:

"Aren't all the best songs the ones you go: 'Nah, this one will never…'? I wish I knew what made for a hit song because I would just do that every day and buy big houses everywhere, but I didn't know!"

Crow's resistance to the song came from the fact that she didn't really write the lyrics. Instead, she took the words from a 1987 poem by Wyn Cooper called "Fun." 

"It was a strange coming-together of a song," Crow recalled. "We jammed up this track and I had a book of poetry in front of me. I started reading it and created the chorus and then thought: 'Well, I'll go back and I'll rewrite the words,' which I did like five times and nothing ever felt the same. I thought: 'I've had to work too hard on this thing, it can't be that good!' Then lo and behold… You just never know what's gonna resonate with people, and that was definitely the anthem of the moment. What a gift!"

Crow was nominated for "The First Cut Is the Deepest" at the 2005 Grammy Awards. She wore a yellow Roberto Cavalli halter dress that had a cut-out that extended across her toned stomach and showed off her belly button. On the same side of the dress, the skirt had a slit that went up all the way to her hip. It was both bold and stunning. The look would be at home at a cliffside resort in Greece, as well as a red carpet event.

The dress's yellow color was a good match for the star's boyfriend at the time: Lance Armstrong. Crow even wore one of Armstrong's yellow rubber "LiveStrong" bracelets on the red carpet. When she presented the award for record of the year that night, Crow went onstage and joked that she had made her dress from Armstrong's old yellow Tour de France jerseys.

Crow and Armstrong dated for two years and were engaged for five months before splitting up in 2006. The couple released a joint statement through Armstrong's spokesman to People after the break-up. The statement read: "After much thought and consideration, we have made a very tough decision to split up. We both have a deep love and respect for each other and we ask that everyone respect our privacy during this very difficult time."

Crow has never been married and doesn't have any children. According to her social media, the star spends most of her time working and is an avid Milwaukee Bucks fan. She also has posted several photos of her enjoying outdoor activities. It seems Crow is still a midwestern girl at heart.

What do you think of Crow's Grammy look? Would you ever wear a dress like that? Let us know your opinion, and be sure to pass this along to your friends and family.