I’ve expressed in several other posts on here that I never really saw Heartbreaker as the amazing album that a lot of other fans do. I feel like it has some good songs and a few that are absolutely amazing, such as “Oh My Sweet Carolina” and today’s song: “My Winding Wheel.” It’s a pretty simple folk song, all built around a loose guitar rhythm and lyrics about lovving someone who has other men on her mind. What’s interesting about it is the fact that this song isn’t sad, though. Rather than sitting around, feeling sorry that he isn’t up to her standards, the narrator is defiant and challenges her to go out and try to find someone better.
The chorus is one of his best. “Buy a pretty dress/Wear it out tonight/For anyone you think could outdo me/Oh, better still/Be my winding wheel” truly says it all. But, to be honest with you, I don’t know what a “winding wheel” could be. I mean, I guess every wheel winds… I just don’t really understand the words in the line. I completely get what he’s saying, but the term just doesn’t really click with me. I feel like this song is the highlight of his folkier material, and I’m surprised it isn’t a regular in his setlists.