My Favorite Mistake by Sheryl Crow

Album: The Globe Sessions (1998)

Charted: 9 20

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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.)
The video is pretty straightforward, with Crow miming and vamping to the song in an unadorned room. It was directed by Samuel Bayer, who used the sepia look and film transitions that show up in a lot of his work.
Eric Clapton clearly didn't have any hard feelings about this song or his breakup with Crow. He appears on her 1999 album Sheryl Crow and Friends: Live From Central Park, where he performed "White Room."

Comments: 10

Amy from CtEvery woman on the planet can relate to this song
Youknowyouknow from United StatesOMG….If it makes you Happy Happy Happy Happy Happy
Don't be unhappy….you're no music fan…
Richy from Birmingham,englandSheryl is just amazing, I would just love to make her my favourite mistake!! P.s. I have made plenty of those and this song really hits the spot and I can relate to it. Wonderfull, thankyou Sheryl.
Dane from Lima,ohio, FlThis is one of her better songs.(Altho I like"Home" "If it makes you happy"or "The difficult kind" a lot better)This CD or the 2nd one are my favorites.
Theresa from Murfreesboro, TnThis song just screams the truth, I love the album - one of my favorites.
Mike from Hubbard, OhShe plays this on "Eric Clapton and Friends in Concert A Benefit for the Crossroads Centre at Antgua" DVD. She plays bass- wearing a dress and army boots with short black hair. I think female bass players, expecially Sheryl, are hot! I like all of her tracks.
Adrian from Brookings, SdThis and "Anything But Down" are the weakest songs on "The Globe Sessions" which is saying a lot because they're both still really good songs. That album was her creative apex and by far my favorite in her catalog. I'm not going to lie, I've had a crush on Sheryl Crow for years. She's sexy, talented, down to earth and I don't care what anyone says, the woman can straight up sing!
Mark from Ascension Island,so. AtlanticI bought the DVD "The very best of Sheryl Crow" This song along with 14 of her other great videos. Love her music
Musicfan from New York, NyHer voice is one of a kind, alright... I think this woman is a LOUSY singer and I'm amazed she gets any airplay at all. Her songwriting is pretty interesting, but her singing, hmmmm... Every time I hear her 'belt out' "If it Makes You Happyyyyyyyyyyyyyyyyyyy", I look for the volume control on my radio. :-)
Bethany from Carrier Mills, IlI can't believe that there are only two comments on this song. This is one of the best songs she has ever come out with ... although it is Sheryl Crow so there is so many. I love her... and I think that she is one of the most talented women singer/songwriter in music still today. Her voice is unmistakeable one of a kind. Nobody sounds like her... and she don't let that go to her head. she is who she is... and it doesn't matter what people think.

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