My Favorite Mistake

The song is rumored to be about Eric Clapton, whom Crow dated for a while, but she says it's definitely not about him. "I can't look at that relationship as a mistake," she explained. So who is the mystery man? The song pre-dates her relationship with Clapton and comes from a time when she left Los Angeles and briefly moved to New York City. "I'd been engaged, and I was out of my engagement," she explained to People in 2023. "I uprooted myself and moved and was really, really raw from a relationship I had had that was just simply a very bad idea. A lot of that record was weeding through the upheaval, digging through the subterfuge."

Crow learned from Carly Simon that it might be a good idea not to say who the song is about. Simon has never said who her 1972 song "You're So Vain" is about, which has kept people talking about it. Like Simon, Crow dated many high-profile guys, making the song rife for speculation. Among her paramours: Kid Rock, Lance Armstrong, Jakob Dylan, and Owen Wilson.

In a 2015 interview, we asked Jeff Trott, Crow's frequent songwriting collaborator and guitarist, to weigh in on the mystery. He said: "I've never ever talked to Sheryl about it – never, ever. One of these days, I'm just going to like throw it out there. Everyone just assumed it was Eric Clapton, but I thought it could be Jakob Dylan from The Wallflowers. The Wallflowers supported Sheryl Crow when I was in her touring band. But she dated Eric Clapton for a little while, for about six months... But he was really into Sheryl, big time. I thought for sure they were going to get married. I think the real deal is that he really wanted to have a very traditional marriage, meaning that Sheryl would take care of things, in a traditional housewife role. At the time, this was like when she was pretty much peaking and playing everywhere, and she would've had to give that up." (Here's the complete interview with Jeff Trott.)