I don’t remember much about this one - I think I saw clips on Siskel and Ebert, though. The main character is a fan of authentic blues music and follows a singer of that type who is down on his luck - he’s the opening act for a faux Blues act that sings something like “Ive been plowing my field, harvesting cotton all day long” (which is ridiculous, of course).
Could be Cadillac Records? Vaguely matches description but can’t recall a scene like that (not seen it ages however)
It kind of sounds like the blues an character from Kids in the Hall.
Crossroads?
I need to add some more background - though the main character is a blues fan, he’s not a musician and not really close to any musicians. It’s just a character trait that he loves “authentic blues.” I think the movie itself is about his mundane life, taking dates to bars where bluesmen play and boring the dates with his lectures about the true blues.
Ghost World?
That’s it!
The lyrics are even worse than I thought - “Plowing in my fields, picking cotton all day long”