The 1998 Song Sheryl Crow Will Never Tire Of Singing Isn't Her Biggest Hit

Rarely do artists share the same opinions about their work as the general public. If you ask Sheryl Crow to play her favorite song, she's not going to play the funky, clean electric opening to her biggest hit, "All I Wanna Do" — a song that helped make 1994 the decade's best summer for music. She'll play a song that might be related to its subject matter, though: "My Favorite Mistake."

That's right. While Crow's breakout and biggest single reached No. 2 on the Billboard Hot 100, it's the lesser-charting (No. 20) "My Favorite Mistake" that remains the song she's most proud of. As Crow said on "The Bobby Bones Show" podcast in 2026 (per Parade), "It's the only song when it comes on the radio, I don't turn it off ... I don't overanalyze it, criticize it, whereas other things I go, 'Gosh, I wish I would have done this or would have done that.'" This makes sense musically, as the song is textured, has a good balance of singable simplicity and instrumental depth, and even lets Crow play bass (which she's done more and more over time). We could even add it to a list of nearly perfect Sheryl Crow songs that belong on every country rock playlist. On the other hand, Crow's love of the song might seem unusual since you'd assume artists feel sensitive about dredging up old breakup feelings. 

Then again, the song's subject matter might be part of why Crow likes it. As she told Howard Stern in 2022 (via YouTube) of the song's muse, "There've been several other favorite mistakes since him." 

We don't know the full story of how Sheryl Crow wrote "My Favorite Mistake," who it's about, why it matters so much to her, and why she feels so non-critical about it. For awhile, folks thought it was about Eric Clapton, which Howard Stern jokes about in his aforementioned 2022 interview with Crow. But Crow has never and likely will never say exactly who the song is about. She released it on 1998's "The Globe Sessions," but the song's origin predates her time with Clapton.

Crow has, however, revealed the circumstances surrounding "My Favorite Mistake." As she told Stern, the song came from her time dating a person who had previously been involved with two other people at the same time. Crow and this person's relationship ended, and she wound up dating several more "favorite mistakes" over the years. In other words, the song has enduring meaning to Crow on top of a timeless sound and excellent songwriting. No matter the lack of publicly confessed specifics, the song is very personal and came from real life. 

Contrarily, Crow's biggest hit, "All I Wanna Do," was a last-minute album addition to 1993's "Tuesday Night Music Club." She was reluctant to include the song on the album largely because she didn't write the lyrics, which rendered it impersonal. As she told The Independent, the lyrics were basically lifted from a 1987 poem called "Fun." She doesn't despise "All I Wanna Do," though; she considers it "a gift." Nonetheless, it's a gift she feels less strongly about than something that came purely from her.