The Meaning Behind “My Favorite Mistake” by Sheryl Crow and the Mystery Relationship It Chronicles

When Sheryl Crow released “My Favorite Mistake,” people immediately speculated about who the song might be about.

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By 1998, Crow was already one of the biggest stars in music, and the paparazzi were obsessed with her personal life. But, more importantly, Crow had established herself as one of the era’s most prolific songwriters and producers.

Meanwhile, she continued her impressive run of hits with The Globe Sessions. Though the press was stubbornly preoccupied with Crow’s relationships, her songs helped define the era. She led a decade of influential female songwriters, including Sarah McLachlan, Fiona Apple, PJ Harvey, Sinéad O’Connor, Natalie Merchant, and Alanis Morissette.

“My Favorite Mistake” made tabloid catnip and turned a broken relationship into the kind of breakup anthem Carole King would be proud of.

The Perfect Ending to a Bad Day

“My Favorite Mistake” was the first single from Crow’s 1998 album The Globe Sessions. The song is about a cheating ex. However, Crow can’t bring herself to hate her former partner—out of all the bad ones, he’s her favorite.

I woke up and called this morning
The tone of your voice was a warning
That you don’t care for me anymore
I made up the bed we sleep in
I looked at the clock when you creep in
It’s 6:00 a.m., and I’m alone

In the song, Crow explains how her friends feel sorry for her, and the singer predicts her ex will soon be overwhelmed by guilt.

Now, here comes your secret lover
She’ll be unlike any other
Until your guilt goes up in flames
Did you know when you go, it’s the perfect ending
To the bad day, I’d gotten used to spending
When you go, all I know is you’re my favorite mistake
You’re my favorite mistake

Crow wrote “My Favorite Mistake” with her longtime collaborator Jeff Trott. Trott and Crow also co-wrote her hits “If It Makes You Happy,” “Every Day Is a Winding Road,” and “Soak Up the Sun.”

Who Is the Mistake?

Many speculated the song is about Eric Clapton, whom Crow dated in the ’90s, but she said the song predates Slowhand.

She told People, “It’s still so personal to me that I don’t know that anybody knows who it’s about. I guess it’s my ‘You’re So Vain’ moment—I Carly [Simon]-ed it. People thought it was [about Clapton] because I had been dating him for a little bit; I love Eric, and I admire him, but the song was older than that.”

Simon never revealed the subject of her 1972 hit “You’re So Vain,” but she later admitted Warren Beatty is the subject of the second verse.

While writing The Globe Sessions, Crow left Los Angeles for New York after a relationship (and engagement) had ended. The broken relationship and the unnamed partner threaded much of her writing, including “My Favorite Mistake.”

“A lot of that record was weeding through the upheaval, digging through the subterfuge,” she said.

Taking Control

Following her stunning debut Tuesday Night Music Club, public disputes between the album’s songwriters soured their relationships. Crow shrank her circle of co-writers and took control of her albums. She continued as the producer and primary songwriter on her third album, The Globe Sessions, which reached No. 5 on the Billboard 200.

The lead single, “My Favorite Mistake,” was a Top 20 Hot 100 hit and reached No. 5 on Billboard’s Mainstream Top 40 chart. Crow received a Grammy Award for Best Female Pop Performance for “My Favorite Mistake” and The Globe Sessions earned a Grammy for Best Rock Album.

She recorded “My Favorite Mistake” at Globe Studios in New York and Sunset Sound Factory in Los Angeles. The song features both Trott and Wendy Melvoin from Prince’s Revolution band on guitar. Tchad Blake mixed the album and won a Grammy for Best Engineered Album, Non-Classical for his work on The Globe Sessions. (Blake also won two Grammys for his work on The Black Keys’ 2010 masterpiece Brothers.)

Alone in the Music Video

Samuel Bayer directed a sparse music video for “My Favorite Mistake.” Crow performs alone in a narrow room while occasionally playing her bass guitar.

The video’s color scheme and treatment are very ’90s, with dark textures and dramatic images of Crow staring blankly off-camera. If you watched MTV in the ’90s, you’d often see artists staring off “somewhere,” with Pearl Jam’s “Jeremy” being the most notable.

Bayer also directed two of MTV’s touchstone ’90s videos, Nirvana’s “Smells Like Teen Spirit” and Blind Melon’s “No Rain.”

I Bet You Think This Song Is About You

In the ’90s, Sheryl Crow songs were ubiquitous, and “My Favorite Mistake” was Crow’s politer version of Carly Simon’s “You’re So Vain.”

One of Crow’s many gifts is making heartbreak sound so soothing.

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Photo by Jason Kempin/Getty Images

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