“Still a lot of fun to play”: Sheryl Crow’s favourite song of her career

The concept of a legend is a strange one in today’s landscape. For some, it means being around for long enough to make a lasting impression, while for others, it’s less about longevity and more about mystique and endearment. Although the term seems odd for Sheryl Crow, there’s an undeniable weight to her presence, the kind that seems gentle at first, though indisputably there for the long haul.

Interestingly, when discussing the topic and the possibility of being praised as a legend, Crow evaluates the differences between when she gained popularity and today’s landscape. Like many, she shares the view that had she tried to make it today, the pressure to promote herself using modern, digital marketing tools would have held her back, stagnating her momentum in inexplicable ways. Stevie Nicks also noted Crow’s interesting placement in music history.

While assessing Crow’s impact on the industry, Nicks once said she would have thrived better if she had been around the same time she blossomed, enjoying the scene with unwavering freedom and liberation in ways she never could when she did emerge. “I’ve already gone through everything she could possibly think of going through,” Nicks once said, observing how Crow’s quiet defiance mirrored everything Nicks encountered in the previous years.

On the subject of her own impact, Crow acknowledges the different generations while enjoying the one she came from, in spite of all its flaws: “I’m from a different generation,” she bluntly reflected to Vanity Fair, “but I always liked the mystique: I was the girl who wanted to meet the guys standing in front of the airplane who had their packages showing in their jeans— Led Zeppelin.”

However, for most people, it’s not Crow’s extensive years in the business that necessarily make her a legend. In fact, it actually stems from all the reasons you might expect, even of today’s artists who face a constant stream of social media pandering. For Crow, her legendary status came from her ability to seamlessly blend different musical tropes, resulting in an effortless cocktail of forward-thinking tunes.

Of course, Crow’s authenticity and ability to blend personal experience with sonic diversity underscore many of these. ‘My Favorite Mistake’, for instance, was inspired by a cheating ex (who some think was Eric Clapton), not only proving Crow’s proficiency with raw songwriting but also demonstrating her knack for sonic evolution, blending equal parts simplicity with musical intricacy.

Incidentally, it’s also Crow’s favourite song. “My favourite single is ‘My Favorite Mistake’; it was a lot of fun to record and it’s still a lot of fun to play,” she told the BBC in 2005. Despite all of the speculation the song evoked after release, especially regarding the details of Crow’s private life and whether the song was, in fact, about Clapton, it’s easy to see why it earned the top spot among her favourites.

Appearing as a typical, considered rock song, ‘My Favorite Mistake’ isn’t as distinctly Crow as some of her more obvious hits, making it feel like something of an overlooked gem when discussing the broader impact of her legacy. However, it’s precisely these moments that deserve focused attention, revealing Crow as an artist who may have seemed understated in her influence.

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